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Manchester-by-the-Sea Vacation Rentals

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    All 170 Rentals in Manchester-by-the-Sea
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    Manchester-by-the-Sea
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Manchester-by-the-Sea
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Manchester-by-the-Sea
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Manchester-by-the-Sea
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cottage was built in the 1920s and recently renovated. At the end of a long driveway on the back of an old estate, it is very private and yet within 10 minutes walk of Singing Beach and less than a mile from the town of Manchester. So there is easy access to shops, restaurants, and even...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Manchester-by-the-Sea
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    Booth Cottage Ocean view, private path to beach. Private mowed path, ten minute walk to village, harbor, 2 parks, on the commuter rail, four bedrooms, three full and one 1/2 bath, extra large lawn for ball playing, large porches, high ceilings, large windows. 3000$ per week, lower rates off...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Manchester-by-the-Sea
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
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    About this property
    Completely renovated 3-4 bedroom, 1.5 bath. Spacious designer kitchen w/ stainless steel appliances. Large Living room, Dining Room, Family Room (optional bedroom) (first floor) and three bedrooms (second floor). Close to town center, commuter rail, and Singing Beach. 4 minute drive to Singing...
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    Manchester-by-the-Sea, Cape Ann 01944
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    The following rentals are within 15 kilometres of Manchester-by-the-Sea.
    ChestnutSweet, for a sweet New England get-away!1 / 25
    (46)Excellent
    Marblehead
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Housekeeping Included
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2018
    We returned to Chesnut Sweet for our 4th visit and continue to be amazed at the attention to detail in anticipating our every need. The Sweet is in a perfect location that...
    Reviewed May 28, 2018
    Great accommodation with excellent design, finish and very well maintained Marblehead is a lovely town with great views, bars and restaurants The owners were very friendly and...
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    About this property
    Chestnut Sweet, in Marblehead's historic Shipyard neighborhood, is a romantic, private hideaway offering new, top-drawer cottage furnishings and services, easy access to town and beach, and hosts who will welcome you like family. We're within sight, sound, and salt-water air of the ocean for guests...
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    Marblehead, Massachusetts 01945
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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    Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet1 / 23
    (33)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Parking
    • Cable/satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2018
    June 22, 2018As two old Englanders’ visiting New England we have had a wonderful week here. We last visited 10 years ago in November, so needless to say, the weather has been...
    Reviewed May 23, 2018
    My husband and I rented the cottage for a short getaway after our wedding in Kennebunkport, Maine. After the hubbub of the wedding, it was nice to have this quaint cottage to...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2018... we're honored to celebrate our 9th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home away from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Sail Loft of Bearskin Neck1 / 17
    (1)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Reviewed August 6, 2018
    We loved our stay at the Sail Loft—the apartment has all the amenities we needed (including air conditioning!) and was a pleasure to cook and relax in. If you like being in the...
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    About this property
    The Building was once the historic Sail loft- oozing with character and charm. Inside is a 2 Bedroom, 1 Bath apartment unit. A good sized living area with a leather couch, TV & dining table that can fit up to 6. There is a small patio in front with a table, bench and 2 chairs. Great views of White...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 27
    (17)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2017
    We had a fantastic holiday in Gloucester. Summer wind was the perfect location - the house was beautiful, with all mod cons and fabulous views over the harbour. It was also...
    Reviewed May 24, 2017
    We recently stayed at Summerwind Cottage in Gloucester MA. We thoroughly enjoyed our stay. The decor was wonderfully New England cottage. The living area was cozy with lots...
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    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill1 / 21
    (5)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2016
    We really enjoyed our stay. Originally from Massachusetts, we looked for a place that would be interesting and relaxing. The rental is perfect. We were comfortable, had...
    Reviewed February 19, 2016
    With two bedrooms, a convenient, well-stocked kitchen, and a homey living room, the Salty Dog was just what we needed for a family getaway to Rockport, MA. Owners were friendly...
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    About this property
    The Salty Dog Summer Stay is a spacious, bright, furnished apartment with all the comfort and amenities one may need to enjoy time in our seaside town. Perfectly located on Atlantic Avenue in the Old Garden Beach neighborhood, many of Rockport's shops, restaurants, and attractions are a short walk...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2016
    The Seaward is the perfect getaway! I travelled from Boston to Rockport to take a little break from the city with my boyfriend. It's about a 50 minute drive or you can take the...
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    About this property
    Formerly Seaward Inn, 'The Seaward' continues to offer a spectacular setting and charming accommodations. Here you can fully relax while listening to the ocean waves. Experience the charm, serenity, and unspoiled beauty that is The Seaward. Suite 205, also known as Gully Point, offers...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    One Bedroom Loft Apartment B at Cedar Hill Farm B & B1 / 6
    (1)Excellent
    Essex
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2017
    This was our first stay in a B&B, it did not disappoint! It was very clean, cozy and conveniently located to the town of Essex. Appreciated the breakfast choices, especially...
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    About this property
    We can now offer Apartment B to our options at Cedar Hill Farm B & B. This apartment is identical to Apt. A also located in our lower barn. The bedroom is on second floor with open to living area and cathedral ceiling. 8 Foot sliders open to open pastures, woods and meadows. Guests can enjoy...
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    Essex, Cape Ann 01929
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Relax and enjoy the summer in Marblehead1 / 16
    (2)Excellent
    Marblehead
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Grill
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2017
    What a lovely, homey place to stay for 4 adults and 2 children! A beautiful home, well furnished, tastefully decorated, clean and cozy, in a quiet neighborhood. Plenty of...
    Reviewed August 14, 2015
    Wow! Great summer stay and family reunion in Marblehead, thanks in no small part to this absolutely pristine home. The photos do NOT do this home justice. The feel is...
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    About this property
    Located only three blocks from Devereux beach and ln a quiet neighborhood, our house, renovated in 2014, is the perfect getaway for the summer. It is walking distance to downtown Marblehead, restaurants to a movie theater...The house, fully renovated in 2014 can comfortably accomodate 6 people. The...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Ocean Views
    • Terrace
    • Waterfront
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seaward offers a spectacular setting and charming accommodations. Loblolly Cove, offers accommodations for up to 4 people. One bedroom has a queen sized bed, while the rather spacious living room has accommodations for two more. At Loblolly Cove, you will enjoy a deck with ocean views and...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Quaint Seaside Village Studio Steps  From Beach1 / 12
    (6)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    What a wonderful place!! I had the upstairs to myself as well as a living room. Wendy has thought of everything! Very hospitable. I wish I could have stayed here for a month...
    Reviewed March 6, 2017
    We so much enjoyed this cozy little apartment! It is a great find and well kept with everything you need to enjoy your stay in Rockport. Walk to Bearskin Neck in the heart of...
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2018!!. DEDICATED OFF-STREET PARKING FOR ONE CAR. BEST LOCATION IN ROCKPORT steps away from everything! Ground floor studio boasts comfortable and clean efficiency with AC, cable TV and microwave kitchenette, private entrance, private bathroom all on the ground...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • DVD Player
    • Patio
    • Shared Garden
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    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 22, 2014
    We stayed in this fantastic house for over a week with my husband, my sister and her husband. What a wonderful find and what a beautiful place Rockport is. Cannot recommend it...
    Reviewed August 3, 2014
    We stayed in this lovely two bedroom home for two weeks and enjoyed every minute. The location was convenient to down town and various walking trails as well as the other...
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    About this property
    Rockport, a part of Cape Ann, is one of the most scenic towns in Massachusetts located on Boston’s North Shore, Rockport and nearby Gloucester are filled with attractions: art, music, shopping, beaches, whale watching, boating, fishing, bicycling… you name it! Historic Lexington, Concord & Boston...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Captain Quarters1 / 14
    (4)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed July 23, 2018
    Changing Tides is true it's name. I arrived stressed and tired from my daily grind but, left relaxed, rested and full of wonderful memories! Stephanie and Jay are more than...
    Reviewed July 8, 2017
    We stayed for three nights over the July 4th holiday. Perfect location for walking to most places. There is parking right next to the house which is a real bonus in Rockport...
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    About this property
    Captain's Quarters,at Changing Tides Bed and Breakfast, features a queen-sized bed, two skylights and a shared bath, sleep well and look forward to a gourmet breakfast. Beaches, downtown shops and galleries are all within a short walk of our home. This room is located in the front of our home....
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The Harborfront, Beverly/Salem, Boston North Shore1 / 26
    (4)Excellent
    Beverly
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Parking
    • Waterfront
    • Wi-Fi
    • Porch
    • Air Conditioning
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 26, 2018
    Husband and I enjoyed our 2 nights here and wish we could stay longer. As usual, Kathy thinks of all the amenities a guest could need—including luxurious toiletries and plush...
    Reviewed September 21, 2017
    Excellent stay: very good reception and coordination. A very nice stay in comfortable apartment. View from 3rd floor was great. Kitchen well supplied. Convenient location.
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    About this property
    Welcome to the Harborfront House, located at historic Independence Park and Beach on Lothrop Street, recently recognized by the Boston Globe as one of the “20 Best Streets in Boston and Beyond'. You will be instantly captivated by the waterfront activity just steps from the front...
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    Beverly, Massachusetts 01915
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 25
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Balcony
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    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 25, 2017
    Lovely apartment, with bonus deck for enjoying a BBQ & wine. Views of the working harbor can be enjoyed right from the bed (which is super-comfy!). Well equipped kitchen, all...
    Reviewed November 24, 2017
    One of the best vacations I've had in years. The owners were charming and attentive but also respectful of my privacy, which is important to me as a writer. The deck was a...
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    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cozy Beach Cottage in Marblehead1 / 21
    (1)Excellent
    Marblehead
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 29, 2017
    The owners were very accommodating, and the ocean is a few houses down the road which made a lovely walk to watch the sunrise and the sunset. It was relaxing sitting in the back...
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    About this property
    Come enjoy our 3 bedroom Marblehead home located in a quiet, private neighborhood that is full of sun. Just a few houses down from Salem Harbor, the house is situated near a boating beach where you can enjoy the beautiful views or take a kayak out right into the harbor. Beautiful swimming beaches...
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    Location Information
    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed October 27, 2016
    We just completed our first visit here and plan to return to this house. A Very clean, historic home that more than met our expectations. It is off the beaten path with both...
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    About this property
    Down a quaint lane you will find an Artists cottage and guest suite. The smaller of the two buildings contains a private double bed retreat with en suite, cable TV & Wi fi. The Main house boasts a charming loft bedroom with 2 ex-long twin beds. The ceiling of the second floor bathroom is a large...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN1 / 19
    (1)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Grill
    • Ocean Views
    • Waterfront
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    • Balcony
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    Our third Year at The Seaward, Nancy is a fantastic host, always. We love the apartment, and it always feels like we are at home. The weather was beautiful as always and the...
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    About this property
    This newly renovated ocean view apartment at the Seaward exudes classic coastal charm. Here you will fully relax while listening to the ocean waves. Lover’s Cove features exposed brick walls, newly conditioned hardwood floors and a king bed. This seaside apartment makes for our most spacious...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
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    • Waterfront
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gloucester Waterfront Waterfront Vacation House with Dock Direct riverfront home with dock overlooking Annisquam River, Lobster Cove, Wingaersheek Beach, and out towards Ipswich Bay. Open living spaces with endless views of both the river and marshland. This is true waterfront living! So...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    • Private Garden
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 14, 2017
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed March 15, 2017
    I had a wonderful stay at this lovely charming bed and breakfast. Location, accommodations and hostess were excellent.Highly recommend!
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    About this property
    Are you looking for a conveniently located affordable place to stay while you enjoy all that Rockport has to offer? Are you traveling with family or friends and would like the privacy of separate rooms? Our top floor guest rooms (2 available) are perfect for travelers on a budget. Clean and...
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    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Marblehead
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor private guest bedroom with...
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    Location Information
    Marblehead, Massachusetts 01945
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Reviewed August 24, 2016
    This simple seaside cottage is well situated to some lovely views of the coast, including the light houses of Thatcher Island. The cottage itself is well-maintained with a very...
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    About this property
    Walk to the water from this cozy peaceful cottage with ocean views. This bright and cheerful recently updated vintage cottage is just minutes from nearby beaches. Enjoy beautiful sunrises, birds chirping, and leisurely strolls along the rugged coast. Stunning views of the Thacher’s Island Twin...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Waterfront
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spruce Cottage at The Seaward offers a spectacular ocean view setting and charming accommodations. Spruce Cottage, is a quaint and cozy two bedroom cottage with ocean views & fireplace. It has a private queen bed in one room and two twin beds in the other. The living room has a kitchenette and...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    This spacious seaside apartment offers 2 bedrooms, 2 bathrooms, and living room/kitchen with a sunny ocean view dining/game area within a bay window. At over 800 square feet it is our largest accommodation. You’ll enjoy Gap Cove’s seaside charm, with amenities including free WIFI, DVD player,...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Ipswich
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Housekeeping Included
    • Terrace
    • Secure Parking
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Check out lower prices in beautiful month of September. Surrounded by water views on a peaceful cove. Perfect for children. Private beach for Little Neck. A stones throw to Cranes beach and castle. This is a gated community with lovely cottages and friendly neighbors. Private dock to launch your...
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    Ipswich, Massachusetts 01938
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ocean Front Cottage on Scenic Long Beach1 / 26
    (6)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann, MA Ocean front-row cottage (152 Long Beach) has a 270-degree ocean front view and is the last house facing east on the boardwalk of beautiful & sandy Long Beach. Location allows full views of the twin lighthouses of...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Essex
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Bed & Breakfast is located in the small New England coastal town of Essex, MA. on Cape Ann. Historic farmhouse built in 1695 on 18 pristine areas of forest, fields and meadows. First free school in state. Front field used during Revolutionary War for militia training. House completely updated...
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    Essex, Cape Ann 01929
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Beautifully Renovated Antique Home1 / 21
    (1)Excellent
    Marblehead
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2015
    A week was not long enough! We had a wonderful time staying here. Spaciaous, clean, lovely inside and out. Salem is a hop, skip, and jump away, and we also took the train into...
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    About this property
    Vacation in beautiful Marblehead in this wonderfully updated furnished Victorian. Located on a quaint side street only a stones throw to downtown, this 4 bedroom, 2 bath beautiful single family home is sure to help create lasting vacation memories. Carefully renovated chefs kitchen, beautifully...
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    Marblehead, Massachusetts 01945
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beachcomber Suite1 / 11
    (2)Very good
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed July 3, 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed July 19, 2016
    It was wonderful to be with Stephanie and Jay - their home is beautiful and welcoming. Stephanie's breakfast is not to be missed! I especially enjoyed the outdoor spaces - the...
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    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds, and an ensuite bathroom. This sunny room has 2 sky lights, a ceiling fan, AC, a sitting room with a small refrigerator, and a shared bathroom. Stay includes daily multi-course gourmet...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront 2 Bedroom !1 / 14
    (6)Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This was a terrific apartment with a unique opening out to a view of the harbor. It was well appointed and comfortable.There were a few light bulbs out and the exhaust fan in...
    Reviewed January 22, 2018
    We stayed here for a family wedding in Sept. 2017. The apartment was a perfect location(wedding was 8-mns away). It was very well maintain and very,very clean. (Which is our No...
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    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Dragonfly1 / 14
    (2)Excellent
    Gloucester
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 6, 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    Reviewed August 30, 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    About this property
    Spacious home located two blocks from Atlantic Ocean and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat in July & August. Large modern fully equipped kitchen with double oven, 5 burner Viking cooktop, dishwasher, washer, dryer. Three...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    At the Footbridge entrance to Good Harbor Beach1 / 17
    (2)Very good
    Gloucester
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Terrace
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    • Cable/satellite TV
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 1, 2017
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests...
    Reviewed October 25, 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
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    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Back Beach1 / 15
    (2)Excellent
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 31, 2017
    House was wonderful and location perfect. Three generations spending a week making memories and no one was disappointed. Smoke detector battery issue (not something ever...
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    About this property
    Cozy, bright , and ideally located. Unrestricted view of ocean from back of house and large deck. Walk across to Back Beach, 5 minute walk to Front Beach and Main Street downtown. Large fenced yard across from ocean. Beautiful sunrises and sunsets. Train Station 1/2 mile down Granite Street for a...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Year-Round Vacation Home1 / 15
    (1)Very good
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 10, 2017
    5 adultsHouse is in a great location.Very uncomfortable beds unfortunately. (In all rooms!) -wished there was a queen bed instead of a double in ocean view room-) there...
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    About this property
    $1750 (off season) - $2,100 (peak season) per week .... Fresh sea breezes keep the inside cool during the summer and a large fireplace in the living room makes this a cozy winter getaway. The home comfortably sleeps five, has a completely furnished kitchen, a dining room, and a masonry fireplace in...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Vintage Home directly on the Annisquam River1 / 12
    (2)Very good
    Gloucester
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2014
    We had a great time. A couple things you might find helpful. There is a shower in the basement bathroom. This house is not handicapped friendly. All the bedrooms are upstairs...
    Reviewed July 7, 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    About this property
    This six bedroom comfortable house has a large full equipped kitchen with two seating areas. The livingroom has wicker furniture and a stone fireplace. Enjoy the large wrap around deck watching the boat activity from sun up to sun down. Park of the wrap around porch is covered which is great for...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Granite Pier is a traditional Cape Ann home with an unusual history. Built in the mid to late 1800’s, it was part of the Rockport Granite Company housing workmen who mined the nearby quarries. Blending traditional craftsmanship with modern amenities, this home is quintessential New England with...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    Rockport
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
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    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 30, 2017
    Parking was a little tricky and I have to say I was quite concerned when we first arrived. However, Tim was there to greet us and made sure we found appropriate parking for all...
    Reviewed August 7, 2017
    The Beach & King is the perfect vacation home for our four generation family. The house is spacious and beautifully decorated. The front porch is a lovely spot to enjoy...
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    About this property
    Located across from Rockport's Front Beach, Beach & King Beach House is an intimate Cape Ann home located on the North Shore in Massachusetts. Accommodations at our Rockport home offer a picturesque setting with stunning ocean views and a 5-minute stroll to historic Bearskin Neck and the village....
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    Rockport
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Straitsmouth Cove is a classic seaside 'cottage' in a sublime location on Rockport’s Gap Cove. This elegant vacation home has the rambling, comfortable feel of a vintage country manor by the sea. The expansive green lawn, with its incredible waterfront view, is a most serene and awe-inspiring...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    Reviewed January 27, 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Back Beach Cottages - Charming house & guest house1 / 17
    (1)Excellent
    Rockport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2017
    There are two cottages located on the same property. The ocean views are amazing and downtown Rockport is just a short walk away.
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    About this property
    Back Beach Cottages are a unique 2 cottage property with stunning views of the ocean. The location offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The homes are steps away from Back Beach, a 5 minute walk to Front Beach and...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rockport
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    This aptly named home defined as an arrival at land on a sea or air journey offers a welcome respite for the visitor. Tucked away on a quiet side street in the picturesque Village of Rockport, Landfall offers privacy and calm, yet it’s just a short walk to Old Garden Beach and only 3/10 of a mile...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming vacation rental home is situated just 300 yards from Whale Cove. Walk just 1 mile to a sandy beach or into the village of Rockport with its shops, restaurants, galleries and a world class Performance Center. Choose to cook your lobsters in the large, updated eat-in kitchen, which is...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    About this property
    Meet Me on South Street is a charming condo in a 2 unit antique colonial building that is one of Rockport's finest examples of Early American architecture. Lovingly and painstakingly renovated, this two-bedroom getaway is tastefully furnished and comfortable. A sunny pied-à-terre, it is just the...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Sea Mist Cottage1 / 18
    (2)Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Reviewed November 11, 2017
    We came to celebrate our 32nd anniversary. We absolutely loved the Seamist cottage. There were did many wonderful details that were put into this place, we couldn't list them...
    Reviewed August 14, 2017
    We were extremely happy with our stay. The cottage was very clean and had an ocean theme through out. Everything we needed was there! Our daughter (14) slept in the loft and...
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    About this property
    Seamist Cottage is located on a private yard in historic downtown Rockport, Massachusetts, a charming seaside community. Short walks to shopping and art galleries on Bearskin Neck, beaches, train station as well as the Shalin Liu Perfomance Center. We, as new owners, welcome inquiries & feedback....
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet and comfortable vacation rental cottage is just across the street from Folly Cove, one of the most striking coves on Cape Ann. The living room has views of the water (just across the street) and off of the living room is a nice screened porch with views and a granite floor. The large...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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