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Holiday Rentals in Cape Ann, MA

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    Travellers to Cape Ann are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    5 of 5 stars (6) Excellent
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 26
    5 of 5 stars (2) Excellent
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    1 / 15
    5 of 5 stars (4) Excellent
    Rockport
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 13
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    Turn of the century home located two blocks from Atlantic shoreline and close to wedding venues including Elks, Cruiseport, & Anninsquam Yacht Club. 7 day minimum stay Sat. To Sat. Large modern fully equipped kitchen with double oven, 6 burner stove, dishwasher, washer, dryer. Three fireplaces,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 8
    4.5 of 5 stars (4) Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Pet-friendly
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    • ?
    • x
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    • x
    About this property
    Enjoy all that Gloucester has to offer in this charming 1BD cottage by the harbor in East Gloucester. Located on East Main street, so busy during the day, quiet at night. Close to everything by foot or bicycle. $1,150 off season monthly rate from Nov to April. 30 day minimum off season. New gas... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 10 September 2015
    This place is so well-located, well-designed, comfortable and easy! It allowed us a much needed break with access to all the beauty of Gloucester. I loved rocky neck, biking to...
    5 of 5 stars Reviewed 6 August 2015
    This is the perfect cottage for a couple retreat. It is a home away from home. Conveniently located for walks and picture taking. We will defintely stay here again when we...
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    1 / 29
    Gloucester
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Waterfront
    • Satellite TV
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    • Ocean Views
    • DVD Player
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house just steps from the private end of Good Harbor Beach. Open and airy living space with spectacular views of the beach, modern kitchen with all the amenities, large dining area for... View all property information
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    Gloucester, Cape Ann 01930
    1 / 18
    5 of 5 stars (1) Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 15 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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    1 / 21
    5 of 5 stars (3) Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    ABSOLUTELY THE BEST LOCATION IN ROCKPORT - STUDIO RIGHT IN DOWNTOWN AND WITH THE ENTRANCE TO FRONT BEACH just across the street: you are in the middle of everything in our beautiful rental residence. Check the map. More quiet Back and Old Garden Beach are just five minutes away. This is the only... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 18 August 2015
    We had a terrific two weeks staying at this property. The studio was very comfortable, and the location is the best in town. Renata could not have been a better hostess. We...
    5 of 5 stars Reviewed 16 August 2015
    Everything was fine! Thank you so much! My guest was very happy! It was great place for staying in Rock Port!
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    1 / 12
    4.5 of 5 stars (2) Very good
    Gloucester
    6 Bedrooms, Sleeps 12 | Quick View
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    • Porch
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    • Waterfront
    • Central Heating
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed 2 November 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...
    5 of 5 stars Reviewed 7 July 2013
    House is fully equipped with everything you could possibly need. Views are spectacular. Sleeping arrangements are comfortable
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    1 / 7
    4.5 of 5 stars (9) Very good
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Outdoor Dining Area
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    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Inquire Winter Rates Specials Just as sweet as icing on a cupcake - This downtowner located in a court yard makes a perfect getaway since you can stroll to the beach and to all the cultural and seafood eateries located within a stones throw of your front door. The CORNERed INn is designed... View all property information
    Location Information
    Rockport, Cape Ann 01966
    4 of 5 stars Reviewed 28 June 2016
    The owner of this property covered it all - stocked the kitchen with fruit and cheese, eggs, milk,cheerios,English muffins and ice in the freezer to get you started until you...
    5 of 5 stars Reviewed 18 August 2015
    I booked this property based on a few reviews form other vacationers. The location and cottage itself truly exceeded our expectations. The owner, Judy, was wonderful and so very...
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    1 / 18
    5 of 5 stars (2) Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
    • Porch
    • Grill
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Unique round house in quiet private courtyard just behind 40 main St. just steps to Front Beach. The outstanding feature is the rooftop deck with wonderful ocean views and breezes. Have your dinner up there and stay for the magical evening sunsets and stars. Galleries, restaurants, shops,... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 17 July 2016
    Steps to the shops and the beach but on a quiet courtyard, the Round House is a great getaway in a fun space! Phyllis generously offered to pick me up from the station and even...
    5 of 5 stars Reviewed 23 August 2015
    The round house is PERFECT if you are a single or couple looking to enjoy Rockport. My wife and I spent a week in August here. We were lucky enough to have amazing weather for...
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    1 / 11
    5 of 5 stars (1) Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Beachcomber Room, at Changing Tides Bed and Breakfast, features a comfortable king sized bed or 2 twin beds! The large 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 breakfast. Beaches,... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 20 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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    1 / 17
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    About this property
    SPECIAL OFFER: $145 PER NIGHT FROM SUNDAY 8/4 TILL THURSDAY 8/8 FANTASTIC LOCATION - ROCKPORT DOWNTOWN STUDIO ACROSS STREET FROM OCEAN FOR $175 PER NIGHT OR $1,000 SUMMER RENTAL (DOUBLE OCCUPANCY) Beautiful Rockport Downtown Studio Residence after complete renovation in fabulous location:... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 18
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Washer
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 206, also known as Loblolly Cove, offers... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 18
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
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    • x
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    • x
    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.... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 40
    5 of 5 stars (3) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Terrace
    • Waterfront
    • Wi-Fi
    • Balcony
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    All utilities are included. Heat, electricity, water, basic cable. Full hi-speed wifi Sq. footage 1200 sq ft. Full Bathroom with shower Walk in closet Parking: off street Pets Policy: no pets preferred but exceptions upon request Kitchen has a Range/oven and Refrigerator, toaster, coffeemaker,... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 21 July 2016
    This apartment is totally off the beaten path -- in the back of the second floor of an ancient office building, and right on the commercial harbor. You walk up the stairs and...
    5 of 5 stars Reviewed 20 April 2016
    Every window offers a stellar view of the water. In fact, the balcony is actually over the water. This is the best location Glouscester could ever offer. It's a large, weirdly...
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    1 / 18
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Washer
    • Grill
    • Patio
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
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    Gloucester, Cape Ann 01930
    1 / 12
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Enjoy the beauty of Cape Ann at this romantic cottage. Direct ocean front in America's oldest seaport. Immaculate 2 bedroom cottage brings back memories of long ago. At the end of a dirt road, the cottage offers a wrap around porch, rolling green grass, granite steps leading to a flat rocky... View all property information
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    Gloucester, Cape Ann 01930
    1 / 14
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
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    • x
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    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 2 days ago
    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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    1 / 17
    5 of 5 stars (3) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 26 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    5 of 5 stars Reviewed 4 May 2016
    Loved this place. Looks out over the water and was very comfortable. The owner was super, she made sure we had everything we needed and even left a binder full of places in the...
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    1 / 26
    5 of 5 stars (13) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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. <BR><BR>Open living space - large living room with sliding door onto large private deck overlooking... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 29 June 2016
    We had such a great experience staying at Summerwind two years ago that we recently returned. With three teenage boys we found it extremely convenient to have boogie boards...
    5 of 5 stars Reviewed 21 June 2016
    Summerwind Cottage is an absolute jewel! We loved the beautiful, artistic decor, and our hosts, Linda and Hank are just the best. Linda's suggestions were all fantastic. We fell...
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    1 / 17
    5 of 5 stars (4) Excellent
    Rockport
    4 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Grill
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 6 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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    1 / 24
    5 of 5 stars (3) Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Waterfront
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    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 2 weeks ago
    We enjoyed the accomodation and location very much, The locals were very welcoming and helpful. The accommodation was well laid out, the quality was excellent and we would...
    5 of 5 stars Reviewed 13 January 2016
    I grew up in Rockport and went home to visit family and friends. Could have stayed with family, however, checked on what was available in town. This newly renovated furnished...
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    1 / 15
    Rockport
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Internet Access
    • Private Garden
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann 01966
    1 / 5
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Sitting directly on the the beautiful port of Gloucester Harbor, this light and airy 3 room apartment offers full private bath, fully applianced kitchen, king bed and wonderful sitting porch. Walk or bike to local restaurants, museums, theatre and beach, and enjoy all that is Gloucester. The... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 27
    Essex
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    New in 2016! 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, one full bath vacation rental apartment in the heart of historic waterfront Essex village, it also refers to a nautical sailing term which... View all property information
    Location Information
    Essex, Cape Ann 01929
    1 / 25
    Essex
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This delightful vacation rental home offers gracious comfort and easy access to the riverfront town of Essex, with its multitude of antique shops and restaurants. Enter the home via the stately front porch complete with rocking chairs, making it the perfect shady perch to watch the world go by.... View all property information
    Location Information
    Essex, Cape Ann 01929
    1 / 14
    5 of 5 stars (1) Excellent
    Rockport
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    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.... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 1 June 2016
    My mom and me enjoyed our stay in the Captain Quarters. Stephanie and her husband were very nice to us and make us feel comfortable. The breakfast was amazing. The B&B is in a...
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    1 / 20
    5 of 5 stars (1) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Welcome, cher ami ("dear friend"), to this gleaming and immaculate, second floor vacation rental. Cher Ami is available as a summer rental and an off-season rental, with a minimum 2-week rental period. Comprising the upper half of the owner's home (a walk up a flight of stairs is required to... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 2 July 2016
    everything about this place was A+ ,the owners ,the apartment ,the location,the scenery,everything was awesome
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    1 / 17
    5 of 5 stars (1) Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    This delightful pine-paneled 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! From its sun room/sleeping porch, you can enjoy views of the Atlantic or walk... View all property information
    Location Information
    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 3 weeks ago
    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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    1 / 12
    5 of 5 stars (15) Excellent
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed 3 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, hands...
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    1 / 22
    4 of 5 stars (4) Very good
    Gloucester
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • x
    About this property
    LAST MINUTE CANCELLATION allows summer RATE DISCOUNT on authentic English Manor Home reminiscent of the Cotswolds. 'Misselthwaite Manor' is a a quiet respite in a busy world, yet close to everything Historic Gloucester has to offer. Located in the heart of the private peninsula of Eastern... View all property information
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    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed 18 November 2014
    Beautiful home. Open beam construction. Impressive wooden entry door with iron work fixtures. Soothing relaxing music playing in the breakfast room. Walled in yard with gated...
    4 of 5 stars Reviewed 7 September 2014
    We found the house to be in good order. The kitchen had everything we needed to cook once in a while when we didn't dine out. The bathrooms and bedrooms were nice and clean. Lois...
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    1 / 23
    5 of 5 stars (24) Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    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 modern amenities. UNIT #1; --Unfortunately, we are NOT able to accommodate pets of any kind or smoking in the units. --Rates based on... View all property information
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    Rockport, Cape Ann 01966
    5 of 5 stars Reviewed 17 April 2016
    A very well appointed rental within easy walking distance to harbor. Historic area with beautiful landscaping. Many great seafood restaurants and ocean views are minutes away by...
    5 of 5 stars Reviewed 28 June 2015
    My wife & I spent a week here from June 17th to June 24th 2015. We were very, very pleased with everything that was here at Periwinkle # 2. Everything that was shown and described...
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    1 / 15
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    You can't get any closer to New England charm than this condo, called Four Winds, located on Tuna Wharf off Bearskin Neck in Rockport, MA. The view looks directly over the water and is truly picturesque. This is a great place for a getaway providing the choice of cooking in or enjoying the many... View all property information
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    Rockport, Cape Ann 01966
    1 / 21
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    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... View all property information
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    Rockport, Cape Ann 01966
    1 / 22
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Enjoy a peaceful retreat in coastal New England by staying at this lovely Gloucester vacation rental cottage! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will surely become a place you love returning to at the end of... View all property information
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    Gloucester, Cape Ann 01930
    1 / 18
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Songbird, a darling antique vacation rental cottage nestled on a lovely lot in the heart of Rockport Village makes the perfect vacation home base, and is an easy walk to all of the town’s shops, restaurants, galleries, and two beautiful beaches. Watch and listen as the lush, verdant lawn comes... View all property information
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    Rockport, Cape Ann 01966
    1 / 13
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Central Heating
    • Terrace
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    Brand New Listing. The apartment is located on the top floor of my home, located in the picturesque and quaint neighborhood of Rocky Neck, home of the oldest working art colony in the US. The space is light and airy with skylights throughout. The large deck has beautiful views of the water. There... View all property information
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    Gloucester, Cape Ann 01930
    1 / 17
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
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    • ?
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    • x
    About this property
    This delightfully summer vacation rental cottage, overlooking broad stretches of the Atlantic and Rockport's Hoop Pole Cove, is a perfect retreat for anyone looking to experience the best of what New England has to offer. Complete with two air conditioned bedrooms, an expansive yard, and a... View all property information
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    Rockport, Cape Ann 01966
    1 / 12
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
    • Waterfront
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    • Ocean Views
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    • Pet-friendly
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    • Smoking allowed
    • ?
    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... View all property information
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    Gloucester, Cape Ann 01930
    1 / 15
    Rockport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • x
    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... View all property information
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    Rockport, Cape Ann 01966
    1 / 60
    Essex
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This 6 bedroom/5.5 bath waterfront vacation home complete with squash & tennis courts, gym, locker room, kayaks and more. Available on a weekly (or nightly) basis year round, Clamshell Landing is perfect for family vacations, family reunions, corporate outings or other events. Or, bring your own... View all property information
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    Essex, Cape Ann 01929
    1 / 30
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Taking its name from the glorious sunsets one has the privilege of viewing from each of its rooms and both of its decks, Sunset Cottage is a renovated 2 bedroom, 1 bath cottage in Gloucester’s Thurston Point district. Sunset Cottage sits directly on the tidal Annisquam River and boasts air... View all property information
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    Gloucester, Cape Ann 01930
    1 / 22
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Location, location, location! This adorable ground floor unit has it! In a historic Rockport home, it has been lovingly updated with new furnishings, appliances, paint and details, but retains the antique charms of a large bay window, attractive slate floors and exposed beams. The unit boasts... View all property information
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    Rockport, Cape Ann 01966
    1 / 12
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • ?
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    • x
    About this property
    Granite Courtyard is a charming one-bedroom vacation rental cottage located in Rockport's quaint Pigeon Cove neighborhood, with private deck with water views. Built on the site of a former ox barn out of locally quarried granite, the home creates its own unique vacation retreat experience you will... View all property information
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    Rockport, Cape Ann 01966
    1 / 18
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
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    • ?
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    • x
    About this property
    Situated on the shores of the tidal Mill River on a shaded lot of nearly one acre on Gloucester's Wheeler's Point, this vacation home has its own dock and float. This three bedroom, two bath house is on one level and features an open plan concept with cathedral ceiling and lovely water views. The... View all property information
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    Gloucester, Cape Ann 01930
    1 / 20
    4 of 5 stars (2) Very good
    Essex
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Newly remodeled luxury air conditioned townhome with views of the Great Marsh and Essex river from every room. New master bathroom with separate freestanding soaking bathtub and large shower, heated floors, and granite counter top. The master bedroom has a king size bed, ceiling fan, individual air... View all property information
    Location Information
    Essex, Cape Ann 01929
    3 of 5 stars Reviewed 14 October 2015
    Not as secluded as photos make it look. Owner lives on premises. Just in case you're expecting to be alone. We thought it should have been mentioned in the details. Gorgeous...
    5 of 5 stars Reviewed 17 June 2015
    I booked this accommodation for my in-laws who had never been on the North Shore before. The location can't be beat. Every morning we had breakfast (sometimes brunch!) overlooking...
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    1 / 15
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    $1,600 (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... View all property information
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    Rockport, Cape Ann 01966
    1 / 21
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    • x
    About this property
    Captain's Watch House is a Gloucester vacation rental located just a lane away from iconic Stacey Boulevard. This 3 bedroom/1.5 bath gem is steps away from the harbor, two beaches, glorious Stage Fort Park and the vibrant downtown with a huge array of restaurants, galleries, shops, museums and... View all property information
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    Gloucester, Cape Ann 01930
    1 / 24
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Gloucester, Cape Ann 01930