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Cape Ann Cheap Vacation Rental Deals

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    Travellers to Cape Ann are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    31 Matching Rentals in Cape AnnView all 127 rentals
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    Waterfront 2 Bedroom !1 / 14
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 41
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    NEW!  STUNNING STUDIO w/Scenic Harbor View1 / 25
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The studio apartment is tucked away in on a back lane in a residential neighborhood. There's a deck with views of the harbor where you can hang out under the red umbrella. A...
    Reviewed June 23, 2019
    I highly recommend this adorable apartment- very clean, bed was comfortable, nice views of the harbor and close to everything in Gloucester- perfect stay and Linda is so nice...
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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
    Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet1 / 23
    (44)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
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    • Cable/satellite TV
    • Grill
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2019
    This is truly a home away from home. A short walk to town where parking is at a premium. Stocked with everything you might need, with extra touches like a new kitchen sponge...
    Reviewed July 27, 2019
    Dear Rosemarie and Family!Our second lovely stay in #1 Periwinkle Cottage!So rejuvenating – we had to stay the extra day! We are very grateful for the ease of keeping our...
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    About this property
    OPEN YEAR ROUND - 2 night minimum stay. 2019.. Celebrating our 10th year hosting guests from all over the world! PERIWINKLE COTTAGE - truly a place to call 'a home from home'. This 2-unit, townhouse cottage offers guests privacy and an updated seaside decor with today's modern amenities. (You...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Air Conditioning
    • Secure Parking
    • Grill
    • Private Garden
    • Housekeeping Included
    • Wi-Fi
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Smoking allowed
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    A Glamorous Gloucester Getaway Explore one of America's oldest towns during your stay in this sleek home, featuring an upstairs deck for direct access to the Atlantic's fresh air. Central air conditioning and Netflix streaming capabilities invite visitors to unwind after a day exploring rocky...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Good Harbor Haven Good Harbor Haven is a charming home that would be perfect for your next beach getaway. The home has a lovely interior with room enough for the whole family. It also has complimentary WiFi and cable for your enjoyment. Be sure to take advantage of the lovely yard with gas grill...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Starfish Cottage Walk to the very best of Rockport from this charming family home, an airy, quaint New England escape with private parking, a private patio and gas grill for summer barbecues, a dog-friendly living space, and a prime location within blocks of the beach, the harbor, and local shops...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vintage Rockport Escape Bright colors, rich fabrics, and antique furnishings make this three-bedroom, dog-friendly home truly special. Enjoy a variety of amenities, including a full kitchen, a lush yard, and a patio with a gas grill - all three short blocks from the beach. Located on a quiet...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Ocean Views
    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rustic Rockport Cottage When you stay at this Rockport cottage, you'll have the comforts of home and the beauty of a seaside town all at your fingertips. Featuring high ceilings, gorgeous woodwork, and a large library, this oceanfront home is as charming as it is unique. You'll wake up every...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Olde New House Olde New House is a sublime choice for your next Cape getaway! Spacious and centrally located within walking distance of Rockport's beaches, this property features modern amenities and a well-equipped kitchenette! What's nearby: This apartment is located a five-minute walk from...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    La Boheme RETREAT Studio1 / 26
    (3)Very good
    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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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Located in East Gloucester, Massachusetts wake up in a dramatic furnished waterfront 2 bedroom and one bathroom apartment living at the edge of Gloucester's Inner Harbor. The unit has hardwood floors with an open concept living with cathedral ceilings and windows galore ! Watch the sunset from a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or walk down the quiet lane to Granite Pier and experience the unsurpassed views of the sun rising over the Atlantic Ocean, and of fishing boats moored nearby. The full moon over Granite Pier is spectacular, and even...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Smoking allowed
    About this property
    Located in Rockport's 'the Avenues,' this home offers a quiet and peaceful environment. It is perfect for those who are trying to find a retreat from the everyday noise of the busy city. Stroll along the scenic streets or along the fabled coastal Atlantic Path, a glorious oceanfront walk over the...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This apartment in a lovely 19th Century home is located on a quiet side street in Essex that ends in an adjacent woodland. Connected to the quiet owner's home, this 'cottage' has its own entrance and driveway, so it feels quite separate. Enjoy the birds and wildlife that are certain to be seen...
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    Essex, Cape Ann 01929
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Close to Half Moon Bay1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Grill
    • Terrace
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your morning coffee and breathtaking sun rises on the covered porch, listen to the birds singing before you walk to Half Moon beach for a relaxing day at the ocean. Private entrance, dedicated parking spot on premise, fully equipped kitchen (with fridge, oven, stove, microwave, coffeemaker,...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    • Private Garden
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A large, bright and cheery front bedroom with two Queen size beds – private bath with clawfoot tub and shower. Newly constructed bathroom with vintage fixtures and repurposed woods. Our breakfast room has old pine cupboards, creeping ivy with twinkling lights, lace tablecloths and original vintage...
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    Location Information
    Essex, Cape Ann 01929
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING1 / 12
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 24, 2018
    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
    WEEKLY BOOKINGS ACCEPTED NOW FOR SUMMER 2020!!. 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, WIFI, cable TV and microwave kitchenette, private entrance, private bathroom all on...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    My place is close to walk to or short drive to restaurants and dining, family-friendly activities, the beach, nightlife, whale watching . You’ll love my place because of the coziness , the comfy bed, the relaxed and easy atmosphere, and close proximity to all Gloucester, Rockport and Cape Ann have...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    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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    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    This charming condominium is located on the ground floor of a coastal Victorian era complex. Overlooking Smith Cove and Gloucester Harbor, this romantic getaway is tastefully furnished, boasting a private patio where you can take in the views of the active port. Enter the property from the patio...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • Terrace
    • Private Garden
    • Balcony
    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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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This sweet vacation rental cottage is a short distance to two of Rockport's finest beaches - Cape Hedge and Long Beach. The cozy summer cottage has lovely views, from the back deck and lush yard, of the marsh and Saratoga Creek which handles the glittering tidal flow from the beaches. Beach...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Sea Mist Cottage1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Helen's Way is a quaint and tastefully decorated 3rd-floor apartment that is a perfect getaway for up to 4 people. It has an open and sunny living room, featuring a sofa as well as a day bed with a trundle and flat-screen TV. From the large living room windows, you can catch a glimpse of Good...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Quaint cozy pre-Revolutionary house with priceless view of picturesque Rockport village and Atlantic Ocean. Located on quiet dead-end lane next to tranquil pond and small town park. Two-minute walk to beach and town's attractive Main street with shops, art galleries and restaurants.The new...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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