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Cape Ann Vacation Rentals

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    Travellers to Cape Ann are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 143 Rentals in Cape Ann
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 84
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Periwinkle Cottage - Unit 11 / 23
    (29)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (17)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Charming 2 bedroom Rockport Carriage House1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Parking
    • DVD Player
    • Patio
    • Shared Garden
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 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 3 August 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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    Quaint Seaside Village Studio Steps  From Beach1 / 15
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Grill
    • Balcony
    • Outdoor Dining Area
    • Porch
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 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...
    Reviewed 20 September 2015
    My husband and I stayed in the studio and loved it. The location is great. You are near all the shops in town and the beach is a block away. The train station is nearby and...
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    About this property
    BOOKING ACCEPTED NOW FOR SUMMER 2016!!. 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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    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 20 September 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 27 January 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
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    AFFORDABLE GUEST ROOM BY BEACH, WALK EVERYWHERE!1 / 15
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Satellite TV
    • Internet Access
    • Private Garden
    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Loved our stay at Gloucester Harborview Inn . Great location, spotlessly clean and very welcoming . Highly recommend
    Reviewed 15 March 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 an 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 comfortable, for one or...
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    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Salty Dog Summer Stay at Old Garden Beach1 / 21
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Parking
    • Washer
    • Internet Access
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 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 19 February 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
    Built in 1900, this classic New England beach house is located in the Headlands neighborhood in Rockport, Massachusetts. Steps away is the charming Old Garden Beach, secluded enough to remain a hidden jewel of Rockport. Also a short walk away is the Headlands, providing spectacular views of...
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    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Internet Access
    • Satellite TV
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Remodeled 3BR Gloucester Annisquam River Cottage1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
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    About this property
    Enjoy a peaceful retreat in coastal New England by staying at this lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will surely become a place...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront 2 Bedroom !1 / 14
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
    Reviewed 25 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
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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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    The Mariner - Authentic Rockport Experience1 / 24
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Parking
    • Waterfront
    • Air Conditioning
    • Terrace
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 2017
    We had a great experience at the Mariner. Even if we were a bit off-season, most of the shops & restaurants were open on Bearskin Neck. It's a picturesque town, what you...
    Reviewed 3 January 2017
    Justin is very helpful. The rental is right in the middle of the action in Rockport. The rental is completely modern with all amenities. The internet is even fast! This is a...
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    About this property
    The Mariner is a custom-furnished, luxury apartment with a panoramic harbor view and providing all the amenities and comfort that one may need to enjoy time in Rockport, Massachusetts. <BR><BR>The Mariner, a 2nd floor apartment, is located at 35 Bearskin Neck. The front entrance is on Bearskin...
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    Location Information
    Rockport, Cape Ann 01966
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean Front Cottage on Scenic Long Beach1 / 52
    (6)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Grill
    • Wi-Fi
    • Patio
    • Ocean Views
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Front Cottage Directly on the Boardwalk of Scenic Long Beach - Cape Ann 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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    2 Bedrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, Sleeps 4
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    Oceanfront Cape Ann retreat w/ stunning  views, fireplace, deck, & gas grill!1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Patio
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    We made this rental last minute and were so glad that we were able to get it. It has a wow factor when you arrive. The back deck faces east, so you get the benefit of seeing a...
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    About this property
    Go on a classic New England retreat and enjoy a luxurious stay at this lovely Cape Ann home. You'll have amazing oceanfront views, a cozy wood-burning fireplace, and a great deck with a gas grill for outdoor entertaining. This house is located in Rockport, MA, just 43 miles northeast of the city of...
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    Location Information
    Cape Ann, Massachusetts 01966
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual or couple...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Captain's Cottage: Traditional setting with a private footbridge to the beach1 / 16
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2016
    We stayed here for a week and Loved it!! It's soo private and quite the only thing we could hear at night were the crickets and crashing waves of the Atlantic! The Captain's...
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    About this property
    This delightful vacation rental cottage is located on a quiet Rockport lane less than 100 yards from the sands of Cape Hedge Beach. Just cross the lane and walk over the footbridge and you're on the beach! This cozy two bedroom beach house is pine-paneled, in the traditional summer cottage...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sea Mist Cottage1 / 18
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 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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    Beach &  King Street Inn / Beach House Rental1 / 20
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
    • Satellite TV
    • Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 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 7 August 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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Satellite TV
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Life is a voyage, and Way Point is the perfect place to launch part of your voyage. Way Point is not only the name of this adorable two bedroom vacation rental apartment, it also refers to a nautical sailing term which means 'a stop along the way, or a place to change course.' Enjoy air...
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    Essex, Cape Ann 01929
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Waterfront
    • Internet Access
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Extraordinary views of Sandy Bay from this 2 bedroom 'half a house' in Rockport's quiet and lovely 'Avenues' area of Pigeon Cove have been known to stimulate the poetic side of its inhabitants. Sit in the dining/living area and watch the glittering sea from the wall of windows or outside on the...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, MA, this home is a short walk...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This waterfront historic vacation home is centrally located in the village of Rockport and was home to John Oakes in the late 18th and early 19th centuries. Completely renovated in 2015 and brought up to the highest modern standard, it retains its old world charm. It has wonderful architectural...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Good Harbor House  Vacation Rental-Walk to Beach1 / 12
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    My family and I have stayed at Good Harbor house for the past five or six years. We have been coming to Gloucester every year for more than 20 years. Good Harbor house is...
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    About this property
    This tastefully decorated, immaculate one-bedroom vacation rental is on the first floor of a landmark Victorian, with private entrance off a grand wrap-around covered veranda, overlooking private fenced-in lawn and garden. The covered veranda provides a great cooling respite from the sun in summer...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Front row seats from every room and deck to view glorious evening sunsets over the Annisquam River and Ipswich Bay. Sunset Cottage is a charming 2 bedroom, 1 bath cottage on Gloucester’s Thurston Point that sits directly on the tidal Annisquam River and boasts unparalleled views. Two decks with...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 shores and seafood markets. Dive...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Internet Access
    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2016! Enjoy the comforts of modern day living while you step back in time in this updated colonial-era vacation rental home. From the moment you turn the brass door knob, which is original to the house, you will feel steeped in history. Filled with light from the large windows throughout,...
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    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a beach house, this is it. Walk to Long or Cape Hedge beaches in 5 minutes or just relax at this fun vacation rental home and enjoy the water views from one of two decks. Sea Vagabond House is actually two houses in one; the original cottage downstairs (which was built in...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    • Grill
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious 5 BR vacation rental home is steps from Old Garden Beach as well as a short stroll into the seaside village of Rockport. Make this delightful and immaculate property your home base for your beach escape this summer. The main level of the home consists of the gracious and...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Air Conditioning
    • Secure Parking
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Captain Quarters1 / 14
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Washer
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    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 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...
    Reviewed 2 July 2017
    We stayed in the Captain's Quarters of Changing Tides Bed and Breakfast for four nights. THe room's skylight greeted us each morning with blue skies filtered through the...
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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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    Location Information
    Rockport, Cape Ann 01966
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful summer vacation rental cottage, overlooking broad stretches of the Atlantic Ocean and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of New England. The wraparound porch and expansive yard allow you to fully enjoy Cape Ann's natural beauty....
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Internet Access
    • Grill
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious vacation rental home is the perfect launching place for your Rockport summer adventure. Beachcomber has many large and comfortable gathering places, such as the custom kitchen, living room and separate family room. Equipped for fun, the home offers an electric piano, a ping pong...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Waterfront
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets you will experience from the deck or the delightful gazebo. This home has a brand new custom kitchen,...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mermaid suite, at Changing Tides Bed and Breakfast, features a comfortable king sized sleep number bed. The large sunny room features a sky light, a ceiling fan, AC, and a large ensuite bathroom. Stay includes daily multi-course gourmet breakfast. Beaches, downtown shops and galleries, and the...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedroom Cottage on the Beach!1 / 17
    (5)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Satellite TV
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    We all had a wonderful stay at this ocean front home. The home was very clean and comfortable. The location is great! We had 7 people staying and they all loved it there! The...
    Reviewed 5 October 2014
    We rented this quaint, pretty cottage to celebrate a birthday weekend. Our only complaint is that we didn't have more time to spend here. Jennifer was great to work with-very...
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    About this property
    Sitting directly on picturesque Long Beach, this is the perfect spot for a romantic get-away or a family retreat. With decks in the front and back of the house, sun-chasers and shade-seekers alike will be pleased at any time of day. The cottage is sunny and open with a large eat-in kitchen and...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    Beachcomber Suite1 / 11
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    Fabulous food was awesome, she even irons the sheets! Highly recommend staying here. The breakfast was delicious.
    Reviewed 19 July 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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront Woodsy 3BR Cottage1 / 12
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    Our family of 4 (plus two standard poodles) thoroughly enjoyed our stay at this charming spot in the Lanesville section of Gloucester. The sunsets are spectacular, it's very...
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    About this property
    Imagine yourself walking across the lawn to the ocean, sweetly lapping the rocks. You take off your sandals and put your feet into the cool water. Second thought, jump right in! Great space for activities; near beaches, restaurants, galleries. The Space This cottage has been hosting travelers and...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic 'Gloucester Fisherman at the Wheel' sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM1 / 18
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Ocean Views
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cozy Rockport Cottage with Ocean Views1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    The Pratt House on the Boulevard1 / 25
    (10)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    Nine of us gathered for a family Thanksgiving weekend in this lovely, roomy, comfortable home in Gloucester. Location was perfect - close to walking paths, beach and unique...
    Reviewed 18 November 2016
    Ambience,location, Comfort. this house is a true Home and has everything You could want or need. It was rented for a 10 year Reunion of a Marine squad. Four couples attended...
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    About this property
    Spacious 5 Bedroom Brick Colonial Home located on the Historic Stacey Boulevard with picturesque views of Gloucester's Harbor and the Atlantic Ocean. Look out at the stunning views of local schooners, the light houses, fishing vessels and feel the cool sea breeze that provides refreshment from the...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Cove View: Sweet cottage across from beautiful Folly Cove1 / 29
    (1)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    Cove view cottage is a little gem in our view. We had an amazing 10 day stay here in August and didn't want to leave. The cottage was built in 1805 and has amazing character...
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    About this property
    This utterly sweet vacation rental cottage overlooking Rockport's beautiful Folly Cove has all modern amenities but maintains the ambiance of the year 1805, when it was built. A thoughtful eye has preserved the property's historical integrity while adding modern comforts. Bright and sunny, the...
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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    18th Century Cottage with attached guest suite1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Back Beach1 / 15
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 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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    Location Information
    Rockport, Cape Ann 01966
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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