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Holiday Rentals in Gloucester, MA

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    ₹ 24,683 Average
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    Travellers to Gloucester are booking May dates now. Secure your holiday home today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (9) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    5 of 5 bubbles (15) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. <BR><BR>Open living space - large living room with sliding door onto large private deck overlooking... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 bubbles Reviewed 23 October 2016
    We have just returned from Summerwind Cottage, it is just beautiful. I can honestly say it is the nicest, best equipped place we have ever stayed in. Fantastic layout and the view...
    4 of 5 bubbles Reviewed 30 August 2016
    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.
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Gloucester, Cape Ann 01930
    1 / 17
    4 of 5 bubbles (1) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    At the edge of Good Harbor Beach, one of the very best beaches in all of New England. Good Harbor Beach, less than 1 hour north of Boston, has a fine white sandy bottom, is cleaned daily, beautiful surf. little undertow, incorporates a saltwater creek. Great for children. 1890s 2-storey cottage... View all property information
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    Gloucester, Cape Ann 01930
    4 of 5 bubbles Reviewed 26 October 2016
    Great place to spend a week or more with your entire family. Large house with big kitchen and dining room for family dinners. Walk across the bridge to the beach or sit on the...
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    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    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 01930
    1 / 28
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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 01930
    1 / 27
    7 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the twin lighthouses of Rockport and the scenic Atlantic Ocean from its wrap around porch and decks, you will never want to leave this amazing beach house. The main level includes... View all property information
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    Gloucester, Cape Ann 01930
    1 / 8
    4.5 of 5 bubbles (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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 bubbles Reviewed 9 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 bubbles Reviewed 5 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 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This immaculate beach house has it all: prime Good Harbor Beach location, views, historic charm and modern comfort and style. The original cottage was built as a stone carriage house to a neighboring estate. A wonderful octagonal addition has created a three bedroom/two full bath home that boasts a... View all property information
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    Gloucester, Cape Ann 01930
    1 / 37
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Gloucester, Cape Ann 01930
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Gloucester, Cape Ann 01930
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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 01930
    1 / 33
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 01930
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    New in 2016! Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and newly renovated vacation rental home is a mere 3 minute walk to Long Beach and an 8 minute walk to Good Harbor. After parking in it's circular driveway, enter this pristine one level home with a... View all property information
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    Gloucester, Cape Ann 01930
    1 / 30
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Porch
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    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
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    Gloucester, Cape Ann 01930
    1 / 22
    4 of 5 bubbles (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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 bubbles 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 bubbles 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 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    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 01930
    1 / 7
    5 of 5 bubbles (2) Excellent
    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
    5 of 5 bubbles Reviewed 7 September 2016
    A big, comfortable home, surrounded by woods, a short walk to the ocean, and a short ride to downtown Gloucester or Rocky Neck. A beautiful, well appointed place. Home for a...
    5 of 5 bubbles Reviewed 30 August 2016
    The Dragonfly is a great place to stay for a big group! It is a beautiful home, with so much character and is clearly well loved by Patricia, the owner. It is even better than...
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    1 / 12
    5 of 5 bubbles (15) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
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    • Pet-friendly
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    • 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 bubbles 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 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
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    • Ocean Views
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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 01930
    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 17
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    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
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    Gloucester, Cape Ann 01930
    1 / 12
    4.5 of 5 bubbles (2) Very good
    6 Bedrooms, Sleeps 12 | Quick View
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    • Porch
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    • Central Heating
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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
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    Gloucester, Cape Ann 01930
    4 of 5 bubbles 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 bubbles 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 / 23
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
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    About this property
    This charming, romantic one bedroom townhouse is located in a quiet, seaside neighborhood on the desirable Rocky Neck in Gloucester Harbor. It has water views and boating access and is just steps away from the water. Water/small beach access is around the corner. Rocky Neck is a fun, festive art... View all property information
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    Gloucester, Cape Ann 01930
    1 / 5
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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 01930
    1 / 9
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    One acre up on quiet bluff, with new view deck and windows overlooking the best beach north of Boston, is our four bedroom, two bath house with lots of parking and just 1500 yards from the ocean. Come and stay with your family or friends and enjoy Good Harbor Beach and all of historic and original... View all property information
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    Gloucester, Cape Ann 01930
    1 / 22
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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 01930
    1 / 8
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    On the peak of a hill on Cape Ann with spectacular panoramic, outside views of the beach,back shore, and even outer Boston Harbor. Secluded, but close to everything. Walk to the beach. Located between Bass Rocks and Brier Neck. Close to Rockport.Sleeps 2 -4. Bright, ground level,walk out basement... View all property information
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    Gloucester, Cape Ann 01930
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Perched overlooking the Wonson Cove’s prismatic waters, this 4 bedroom, 2.5 bath vacation rental home situated in Gloucester’s cultural district known as Rocky Neck will take your breath away. From Eastern Point to the Dog Bar Breakwater, from lighthouses to glorious sunrises, the views from Wonson... View all property information
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    Gloucester, Cape Ann 01930
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    New in 2016! You can have it all with Ships Bell House, as this immaculate 3 bedroom/ 2 full bath vacation rental home enjoys amazing water views, including fantastic sunsets. The home has the added bonus of a pass to swim at the fresh water swimming quarry which is the neighborhood's private and... View all property information
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    Gloucester, Cape Ann 01930
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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,... View all property information
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    Gloucester, Cape Ann 01930
    1 / 37
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care and skill is reflected in the soaring ceilings, multitudes of windows and skylights, and warm pine floors, all of which bring the outside in -- yet all is kept cool with central air... View all property information
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    Gloucester, Cape Ann 01930
    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Gloucester, Cape Ann 01930
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Patio
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New in 2016! Enjoy views of Gloucester's outer harbor, and the private sandy beach, across the quiet private road from almost every room in this fantastic vacation rental home. There are two glorious slate patios that flank the front door from which you may also enjoy the views of the sunrise. On a... View all property information
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    Gloucester, Cape Ann 01930
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Parking
    • Satellite TV
    • Private Garden
    Suitability
    • Pet-friendly
    • 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
    Location Information
    Gloucester, Cape Ann 01930
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Private Garden
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    From our convenient in-town location enjoy restful refinement while also delighting in being part of the Gloucester experience. Our 2800 sq ft, easy-to-live-in home is perched above the sparkling waters of Gloucester's inner harbor. Watch the gulls soar and fishing boats return home from the... View all property information
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    Gloucester, Cape Ann 01930
    1 / 5
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
    • Wi-Fi
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    located in quiet, wooded neighborhood. Older summer cottage close to the beach. Very comfortable for families. Good size living room for visiting. Separate dining room. Deck with small BBQ. Warm outside shower for after the beach or anytime. Close to Gloucester with easy access to highway.... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Secure Parking
    • Central Heating
    • Balcony
    • Waterfront
    • Wi-Fi
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Not just near the harbor. ON the harbor. A perfect scene all year-round across the bay of the Harbor, Ten Pound Island and the Paint Factory. Walk easily to harbor restaurants, supermarket, train, THE BEACH. A casual home with exceptional views. The Space Large kitchen and dining area with a view... View all property information
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    Gloucester, Cape Ann 01930
    1 / 11
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Internet Access
    • Terrace
    • Grill
    • Waterfront
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The cottage is an updating of the original Coggeshall artist camp overlooking a grassy acre of land leading to its own point of land jutting into Ipswich Bay. With prevailing calm water the shorefront is usable for swimming and boating (boat launch 1/2 mile at Lane's Cove). The cottage is at the... View all property information
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    Gloucester, Cape Ann 01930
    1 / 53
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
    • Porch
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 to December 31. This newly renovated and updated waterfront gem has four bedrooms and 1.5 baths, a deep-water dock (accommodates up to a 30 foot boat, with our new extended dockage in 2014) and a... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 bubbles Reviewed 3 February 2015
    We try to stay here every year because we love the comfortable quality of a vacation home that's been in the family since 1929. The roomy screened in porch wraps around 3 sides...
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    1 / 51
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Patio
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    LUXURY OCEANFRONT ESTATE CLOSE TO BOSTON This truly unique, breathtaking oceanfront circa 1890 estate has been painstakingly renovated and modernized by its current owner. The property consist of close to 4 acres of direct oceanfront access with a 4,000 sf stone house that boasts an attached... View all property information
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    Gloucester, Cape Ann 01930
    1 / 6
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Updated seasonal waterfront cottage ideal for swimming or kayaking right from the property. It is located on the Northeast shore of Cape Ann, affording sweeping views of Ipswich Bay, with gorgeous summer sunsets over the water. It is nestled in among three other waterfornt cottages in a quiet... View all property information
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    Gloucester, Cape Ann 01930
    4 of 5 bubbles Reviewed 27 September 2015
    We stayed at this glouster harbor house for a wedding weekend. Ten of us stayed comfortably. The house is furnished with everything you need. Dr. Rick was wonderful with prior...
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