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Gloucester Holiday Rentals

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    Travellers to Gloucester are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (10) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 48
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 23
    4 of 5 bubbles (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
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    • Waterfront
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    • Grill
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    • Pet-friendly
    • Child-friendly
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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 / 26
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    4 of 5 bubbles Reviewed 21 September 2016
    This unit was a great location! It was easy to get to the train to go into Boston as well as to travel to other sites in and around Boston. My daughter and I loved to sit on the...
    5 of 5 bubbles Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    1 / 11
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Perfect for 1 or 2 guests looking for an affordable summer get-away in beautiful location. The studio can also accommodate an infant in a pack-n-play or porta-crib, who is not yet walking. Walk to Good Harbor Beach and scenic Back Shore. We call your home away from home, “Good Harbor House”... View all property information
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    Gloucester, Cape Ann 01930
    1 / 12
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Garden
    • Waterfront
    • Parking
    • Wi-Fi
    • Ocean Views
    • Washer
    • Grill
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    • Pet-friendly
    • Child-friendly
    • 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 / 8
    4 of 5 bubbles (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
    • Air Conditioning
    • Parking
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    • Outdoor Dining Area
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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, busy during the day, quiet at night. Close to everything by foot or bicycle. Sunny, furnished, adorable 1BD. Living Room/Kitchenette downstairs, Bedroom/Bath... 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 / 7
    5 of 5 bubbles (2) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Secure Parking
    • Grill
    • Private Garden
    • Patio
    • Washer
    Suitability
    • 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 01930
    5 of 5 bubbles Reviewed 6 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 / 17
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
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    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Parking
    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 01930
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    1 / 17
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
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    • Grill
    • Satellite TV
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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
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    Gloucester, Cape Ann 01930
    5 of 5 bubbles Reviewed 25 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
    5 of 5 bubbles 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 / 12
    5 of 5 bubbles (15) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • 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 01930
    5 of 5 bubbles 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 / 23
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Satellite TV
    • Ocean Views
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 17
    4.5 of 5 bubbles (2) Very good
    6 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Grill
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Satellite TV
    • DVD Player
    • Balcony
    Suitability
    • 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
    Location Information
    Gloucester, Cape Ann 01930
    5 of 5 bubbles Reviewed 3 weeks ago
    This beachhouse is a dream. Classy beautiful old beachhouse yet super comfy and homey. Plenty of room and different spaces to accommodate a family with a variety of interests and...
    4 of 5 bubbles Reviewed 25 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 / 12
    4.5 of 5 bubbles (2) Very good
    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
    • ?
    • x
    • 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 01930
    4 of 5 bubbles 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 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 / 5
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Garden
    • Wi-Fi
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    • Pet-friendly
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    • ?
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    • 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
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    Gloucester, Cape Ann 01930
    1 / 22
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    • Smoking allowed
    • 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 / 37
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • DVD Player
    • Balcony
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    • Grill
    • Terrace
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    • Pet-friendly
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    • x
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    • x
    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 / 19
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Waterfront
    • DVD Player
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    Enjoy the views of the sparkling Annisquam River, lovely Wingaersheek Beach and the Annisqaum Yacht Club just across the river. You'll also be wowed by the incredible sunsets that await you every evening from this 3 bedroom/3.5 bath vacation rental home, which efficiently and effectively packs a... 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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    • Air Conditioning
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • 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 01930
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    1 / 40
    5 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • x
    About this property
    Located above the western shore of Gloucester’s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian vacation rental home has been in the same family since the 1880's. This gracious home gives hints to a bygone era while offering modern amenities. A... View all property information
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    Gloucester, Cape Ann 01930
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
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    • Shared Garden
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    • Pet-friendly
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    • ?
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    About this property
    Cozy two bedroom late 1800's home with updated big kitchen and two bathrooms. TV room, sitting room downstairs. Two bedrooms, full bath and walk in closet upstairs. Shared yard with BBQ grill, outdoor shower. Conv. store and gas station across the street. East Main is a busy street during the... 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
    Ideally situated between two of Cape Ann's most beautiful beaches, this immaculate and recently renovated vacation rental home is a mere 3-minute walk to Long Beach and an 8-minute walk to Good Harbor Beach. The home has a single level and an open floor plan that offers convenience and... View all property information
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    Gloucester, Cape Ann 01930
    1 / 53
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Ocean Views
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Internet Access
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    • 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 / 20
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • 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
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    Gloucester, Cape Ann 01930
    1 / 37
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
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    Gloucester, Cape Ann 01930
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Terrace
    • Balcony
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    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 / 27
    7 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • x
    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 / 25
    3 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
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This... View all property information
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    Gloucester, Cape Ann 01930
    1 / 17
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Barlovento, the Spanish name for “windward,” is also the name of this stunning vacation rental home, which is one of Eastern Point's original summer “cottages.” Built c. 1889, this grand Tudor-style residence seamlessly blends the elegance of its historic past with modern-day amenities and has... View all property information
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    Gloucester, Cape Ann 01930
    1 / 36
    6 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Balcony
    • Terrace
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This luxurious vacation rental home is situated on the highest point of Brier Neck with astounding ocean views from every angle. Ascend the outside steps of this Tudor-style home and observe the rolling lawn on one side and take in the spectacular 240 degree views (and sounds of the surf) of... View all property information
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    Gloucester, Cape Ann 01930
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    This perfectly-located vacation rental is a delightful ground floor apartment (in a two-unit building), right at Good Harbor Beach. With one bedroom and sleeping space for 4, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good... View all property information
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    Gloucester, Cape Ann 01930
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    This delightful 3 bedroom, 1.5 bath Queen Anne-style vacation rental home is bright and cheery and just waiting for you! Enter the house into the kitchen from the verdant and sizable back yard (or choose one of the other 2 doors). The sunny kitchen has plenty of storage, a gas range, and a small... View all property information
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    Gloucester, Cape Ann 01930
    1 / 31
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • x
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    • x
    About this property
    Enjoy the best sunsets on the East Coast from this classic riverfront Victorian summer retreat. Annisquam Singing Pines is situated on over an acre of waterfront land and has lovely gathering spaces both inside and out. It was built as an impressive yet casual vacation home to entertain the family... View all property information
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    Gloucester, Cape Ann 01930
    1 / 38
    6 Bedrooms, 6 Bathrooms, Sleeps 16 | Quick View
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    This spacious and gracious vacation rental home offers incredible versatility to suit your specific vacation needs. The house can accommodate just your family or your extended group of up to 16, making it the perfect getaway for family reunions or vacations with friends. The house has been... View all property information
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    Gloucester, Cape Ann 01930
    1 / 34
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Rosemarc House has stairs that take you directly onto the private portion of Good Harbor Beach. This immaculate 3 bedroom, 3.5 bath luxury vacation rental home is the ultimate beach getaway. Incredible 180 degree views of the whole length of the beach, Salt Island and north up the coast, the... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • DVD Player
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This sweet and comfortable waterfront vacation rental cottage with spectacular sunset views over the Annisquam River offers a wonderful New England retreat. The main floor of the home consists of a charming open living and dining area, a small but well-equipped kitchen, a half bath, a screened... View all property information
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    Gloucester, Cape Ann 01930
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Internet Access
    • Balcony
    • Satellite TV
    • Terrace
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    New in 2017! This bright and open contemporary vacation rental home is the perfect home base for multiple families or groups, having two living rooms and two dining rooms and plenty of space to stretch out. There is also access to private Coffins Beach; choose to walk the .7 miles to the beach, or... View all property information
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    Gloucester, Cape Ann 01930
    1 / 17
    3 of 5 bubbles (1) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A pleasantly bright vacation home situated in Gloucester's charming Bay View neighborhood, Annie's Place radiates an aura of sun and warmth. Only a 10-minute walk to lovely Plum Cove Beach, Annie's Place lets you spend your summer vacation relaxing, discovering local fauna such as hermit crabs, and... View all property information
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    Gloucester, Cape Ann 01930
    3 of 5 bubbles Reviewed 29 July 2015
    Cute house with a terrible parking/road situation. Poorly maintained exterior and patio made walking around the TINY yard dangerous for kids and those with mobility/vision...
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    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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 / 28
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Internet Access
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly... View all property information
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    Gloucester, Cape Ann 01930
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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
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    Gloucester, Cape Ann 01930
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Waterfront
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Sun when you want it. Shade when you need it. Cool Cove is a beach house vacation rental that has it all! Sitting above Wingaersheek Beach, you will feel like you can see forever, enjoying views of Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, and sandbars. Walk from this... 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
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    • 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
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    Gloucester, Cape Ann 01930
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Patio
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 pristine... View all property information
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    Gloucester, Cape Ann 01930
    1 / 27
    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Waterfront
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Oceanside at Good Harbor is a waterfront vacation home directly on Good Harbor Beach, Gloucester's finest stretch of sand. Gracious and beloved, this family-friendly five bedroom summer cottage is set on picturesque Brier Neck. Sit on the waterfront terrace/patio and enjoy the summer breezes and... 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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    • Parking
    • Porch
    • Air Conditioning
    • Washer
    • Satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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 01930
    1 / 21
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New in 2017! Enjoy the ambiance of Victorian Gloucester with all the amenities of the 21st century from this classic period vacation rental home, which is tastefully decorated with the traveler in mind. Enter the house through the front door and enjoy two parlors--one with a large bay window and... View all property information
    Location Information
    Gloucester, Cape Ann 01930
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 24
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New in 2016! Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual... View all property information
    Location Information
    Gloucester, Cape Ann 01930