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Villas and Holiday Rentals in Cape Ann, MA

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    1 / 8
    4.5 of 5 stars (4) Very good
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 26
    4.5 of 5 stars (3) Very good
    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 / 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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    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
    4 of 5 stars Reviewed 27 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 17 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 / 25
    5 of 5 stars (6) Excellent
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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    • x
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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... View all property information
    Location Information
    Gloucester, Cape Ann
    5 of 5 stars Reviewed 19 May 2016
    Our group was extremely pleased with our stay at Pratt House. We enjoyed the large and immaculate living room, dining room, deck and yard. The location across the street from...
    4 of 5 stars Reviewed 10 May 2016
    We are so fortunate that Marilyn shared here beautiful house with us for our annual girl get together. The spacious dinning room, living room and back deck afforded plenty of...
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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
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    • x
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    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
    5 of 5 stars Reviewed 16 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 / 40
    5 of 5 stars (5) 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
    • ?
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    • ?
    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
    5 of 5 stars Reviewed 3 weeks ago
    Great place. Very clean, comfortable beds, well supplied kitchen and the location is something that will no longer exist. Hanging off the harbor, you felt transported by the...
    5 of 5 stars Reviewed 3 weeks ago
    When planning our long Labor Day weekend, I was looking for a place to be away from the hustle of the usual crazy days of life. We found that at our little Condo on the Gloucester...
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    1 / 18
    5 of 5 stars (1) Excellent
    Rockport
    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
    • 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 205, also known as Gully Point, offers... View all property information
    Location Information
    Rockport, Cape Ann
    5 of 5 stars 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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    1 / 21
    5 of 5 stars (3) Excellent
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    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. This is the only rental residence right in downtown and right next to the entrance... View all property information
    Location Information
    Rockport, Cape Ann
    5 of 5 stars Reviewed 17 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 / 14
    5 of 5 stars (1) Excellent
    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
    5 of 5 stars 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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    1 / 7
    5 of 5 stars (2) Excellent
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    5 of 5 stars Reviewed 3 weeks ago
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    5 of 5 stars Reviewed 4 weeks ago
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    1 / 20
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Patio
    • Ocean Views
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in the heart of Bearskin Neck this comfortable 2 bedroom condo is 20 ft to Rockport Harbor. You can sit in the living room, or your deck and watch the comings and goings of Rockport Harbor, and the famous Motif #1. Walk through the nicely renovated 2 bedroom condo, and you can view all the... View all property information
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    Rockport, Cape Ann
    1 / 15
    Rockport
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Internet Access
    • Private Garden
    • Balcony
    • Air Conditioning
    • 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
    1 / 18
    Gloucester
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
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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
    1 / 17
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    **There is a possibility that construction will ongoing near the property during the summer of 2016** Welcome to your very own summer beach home! Located across the street from the North Shore's best beach, this two family home offers five bedrooms, two bathrooms, two separate living spaces as... View all property information
    Location Information
    Gloucester, Cape Ann
    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
    5 of 5 stars 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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    1 / 18
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
    • Waterfront
    • Washer
    • Balcony
    • Terrace
    • Patio
    • Ocean Views
    Suitability
    • 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
    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
    • ?
    • Smoking allowed
    • 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
    Location Information
    Gloucester, Cape Ann
    4 of 5 stars Reviewed 17 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 6 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 / 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
    • ?
    • ?
    • Smoking allowed
    • ?
    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
    4 of 5 stars Reviewed 1 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 / 10
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    The perfect place to relax in Rockport this fall. This cottage offers the best of both worlds: it's a quiet and relaxing spot for enjoying the beach and also close to downtown Rockport. The cottage is steps away from Back Beach, a 5 minute walk to Front Beach, and a 10 minute walk to the heart of... View all property information
    Location Information
    Rockport, Cape Ann
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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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    • 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
    5 of 5 stars 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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    1 / 17
    5 of 5 stars (3) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Waterfront
    • Air Conditioning
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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
    5 of 5 stars Reviewed 25 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    5 of 5 stars Reviewed 3 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 / 15
    5 of 5 stars (1) Excellent
    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
    1 / 26
    5 of 5 stars (14) Excellent
    Gloucester
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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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
    4 of 5 stars Reviewed 4 weeks ago
    The owners Linda and Hank are really nice folks and very responsive. We loved this cottage especially the deck and the living spaces are nicely decorated and very comfortable.
    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...
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    1 / 18
    Rockport
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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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
    1 / 12
    5 of 5 stars (15) Excellent
    Gloucester
    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
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 stars 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, hands...
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    1 / 14
    5 of 5 stars (1) Excellent
    Rockport
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • 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
    5 of 5 stars Reviewed 31 May 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 / 17
    Gloucester
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Grill
    • Terrace
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage... View all property information
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    Gloucester, Cape Ann
    1 / 23
    5 of 5 stars (26) 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. (You can only reserve Unit #1 on this site). UNIT #1; --Unfortunately, we are NOT able to accommodate pets of any... View all property information
    Location Information
    Rockport, Cape Ann
    5 of 5 stars Reviewed 2 weeks ago
    Everything you need is already here except your toothbrush. Wonderful place to stay. Quick walk into town. Try it...you will love it.
    5 of 5 stars Reviewed 2 weeks ago
    Quiet, laid back. Coffee, cream and other snacks upon arrival. Homey and comfortable. 5 star accommodations ;-)
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    1 / 12
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
    • Waterfront
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    • Pet-friendly
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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... View all property information
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    Gloucester, Cape Ann
    1 / 22
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    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
    1 / 5
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • 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
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    Gloucester, Cape Ann
    1 / 13
    Gloucester
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • x
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    • x
    About this property
    This Friday to Friday vacation rental is right at Good Harbor Beach. Step out the door, walk over the Good Harbor Beach footbridge and you are on one of Gloucester’s most highly rated beaches enjoying the sun, sand, and surf. Leave your car in the driveway and enjoy the best of summer; run home for... View all property information
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    Gloucester, Cape Ann
    1 / 23
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    New in 2016! This sweet and immaculate 2 bedroom vacation rental cottage is the perfect place to be this summer, as it is all about the sun, sand and surf of wonderful mile long - Long Beach, which is just about 25 yards from the cottage. The cottage is all on one level, with a wonderful sun... View all property information
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    Rockport, Cape Ann
    1 / 2
    Rockport
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • ?
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    • x
    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... View all property information
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    Rockport, Cape Ann
    1 / 27
    Gloucester
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • x
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    • x
    About this property
    Enjoy this comfortable recently renovated 3 bedroom, 1 bath vacation home 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... View all property information
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    Gloucester, Cape Ann
    1 / 36
    Rockport
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
    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... View all property information
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    Rockport, Cape Ann
    1 / 21
    5 of 5 stars (5) Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 7 | 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
    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... View all property information
    Location Information
    Rockport, Cape Ann
    5 of 5 stars 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...
    5 of 5 stars 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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    1 / 33
    Gloucester
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • ?
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    • x
    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... View all property information
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    Gloucester, Cape Ann
    1 / 22
    Rockport
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    New in 2016! This comfortable 5BR vacation rental home is steps from Old Garden Beach as well as the seaside village of Rockport. Make this delightful, immaculate, spacious and comfortable property your home base to host your beach escape this summer. The main level of the home consists of the... View all property information
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    Rockport, Cape Ann
    1 / 19
    Gloucester
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Waterfront
    • DVD Player
    • Internet Access
    • Satellite TV
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Enjoy the views of the sparkling waters of the Annisquam River and Ipswich Bay beyond as well as Wingarsheek Beach and the Annisqaum Yacht Club just across the river. Don't forget the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which... View all property information
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    Gloucester, Cape Ann
    1 / 32
    Gloucester
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | 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
    New in 2016! Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines offers everything you could want in a vacation rental home, with five bedrooms, two full bathrooms and a tidal dock. The house is situated on over an acre of... View all property information
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    Gloucester, Cape Ann
    1 / 15
    5 of 5 stars (1) Excellent
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • x
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    • x
    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... View all property information
    Location Information
    Rockport, Cape Ann
    5 of 5 stars 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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    1 / 44
    Rockport
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    Walk to Old Garden beach from this immaculate 4 bedroom home that was built in 2008, complete with its own HOT TUB. Just 0.7 Miles from the village of Rockport (and Old Garden Beach) with all its restaurants, galleries and shops, this is the perfect launching pad for your Rockport summer adventure.... View all property information
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    Rockport, Cape Ann
    1 / 15
    Rockport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • 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
    1 / 21
    Rockport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    1 / 29
    Rockport
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • x
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    • x
    About this property
    Rockport Village House is an immaculate and charming vacation rental home that offers versatility, style and convenience. Located on a quiet, residential street and a short walk to all that Rockport has to offer: beautiful ocean vistas, beaches, galleries, restaurants, shops and train to Boston and... View all property information
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    Rockport, Cape Ann
    1 / 30
    Gloucester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Porch
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    This large, comfortable family-oriented vacation home is just steps from the white sands of Long Beach--a perfect summer location! Built in the early 1900's, much of its early charm still remains but is augmented with an updated kitchen and many amenities. On the ground floor there is living... View all property information
    Location Information
    Gloucester, Cape Ann
    1 / 60
    Essex
    6 Bedrooms, 6 Bathrooms, Sleeps 14 | Quick View
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    • Porch
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    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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
    1 / 37
    Gloucester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    A tastefully renovated vacation home, Victorian House on Rocky Neck (Gloucester’s fabled artist colony) has three bedrooms and a gorgeous front porch overlooking the water. From the porch, step into the home’s front hall and formal living room, complete with a custom delicately-tiled fireplace.... View all property information
    Location Information
    Gloucester, Cape Ann