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Gloucester Holiday Rentals

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    Travellers to Gloucester are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 126 Rentals in Gloucester
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    Romantic SUMMERWIND COTTAGE- Scenic Harbor View1 / 26
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    The Pratt House on the Boulevard1 / 25
    (10)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town1 / 42
    (8)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Satellite TV
    • Ocean Views
    • Balcony
    • Parking
    • Waterfront
    • Wi-Fi
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2017
    Every where you look out from inside the apt. is a "new picture of the fantastic harbor and boats going out for the catch of the day". Absolutely gorgeous! There is much...
    Reviewed 22 April 2017
    We really enjoyed our stay here! It felt like you were literally on the water- like in a boat! And the view was magnificent! The apartment was very spacious and well stocked...
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    About this property
    This place is a diamond in the rough - as one of my guests proclaimed. The view is spectacular! The apartment is inside a commercial marine building so it's right on top of the water, where the ships come in to unload lobsters and other catches. The apartment itself is not fancy but very...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    La Boheme RETREAT Studio1 / 26
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Wi-Fi
    • DVD Player
    • Waterfront
    • Patio
    • Central Heating
    • Ocean Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 27 January 2015
    I had a chance to stay at this wonderful studio for 2 weeks and couldn't my believe good luck. This property, a former Unitarian Church and sexton's residence, has been...
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    About this property
    UNPLUG, UNWIND & UPLIFT your spirits! No TV (wifi only). For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Step back in time with this 60's Boho, funky-style studio. Creative objets d'art and romantic lighting creates a very cozy, dark atmosphere (a...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    'Misselthwaite Manor' House Rental & B&B1 / 23
    (4)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Dragonfly1 / 7
    (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
    Kid friendly
    Smoking allowed
    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...
    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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    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,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
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    Good Harbor House  Vacation Rental-Walk to Beach1 / 12
    (15)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    My family and I have stayed at Good Harbor house for the past five or six years. We have been coming to Gloucester every year for more than 20 years. Good Harbor house is...
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    About this property
    This tastefully decorated, immaculate one-bedroom vacation rental is on the first floor of a landmark Victorian, with private entrance off a grand wrap-around covered veranda, overlooking private fenced-in lawn and garden. The covered veranda provides a great cooling respite from the sun in summer...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Satellite TV
    • Washer
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a coastal retreat when you stay at this one-bedroom apartment in Gloucester. Complete with stunning ocean views and a great location near several beaches, this unit has modern amenities inside, along with a lovely patio and outdoor grill. Located in Gloucester, MA, this home is a short walk...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will love this extraordinary waterfront vacation rental home with spectacular views. Set on a bluff over picturesque Strawberry Cove and the open Atlantic, views abound from almost every light-filled room. The house offers three levels of sophisticated, yet comfortable living space....
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this bright and delightfully furnished two bedroom vacation rental apartment. It is the perfect place to stay during your New England summer getaway! Both the living room and the...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    At the Footbridge entrance to Good Harbor Beach1 / 17
    (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
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2017
    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...
    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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    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this vacation rental condo sleeps 8 in central air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named Long Beach is one mile long and spans both Gloucester and Rockport. This...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Satellite TV
    • Grill
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Boulevard is home to the iconic "Gloucester Fisherman at the Wheel" sculpture -- a symbol of the fishing port's rich history as a working waterfront and as the subject of poets,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Hot Tub
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Waterviews & a short walk to Good Harbor Beach. This four bedroom/2.5 bath vacation home is large and comfortable and is just steps to the white sands and surf of Good Harbor Beach. The location offers the best of all worlds as it is so close to Cape Ann's most...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • Balcony
    • Satellite TV
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Balcony
    • Internet Access
    • Satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Internet Access
    • Satellite TV
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
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    • Waterfront
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedrooms, 3 Baths (Sleeps 8) beautiful views, steps to private coffins beach Beautiful single family beach cottage, nestled among the pine trees, located on the private side of Wingaersheek Beach, which is well known as one of the most beautiful beaches on the North Shore, with 1.5 miles of pure...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
    • Wi-Fi
    • Balcony
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    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on a hillside overlooking Gloucester's scenic harbor... enjoy magical sunsets, dining al fresco, twinkling harbor lights, and warm summer winds from the deck of this romantic getaway. This property is best described as a “studio plus”, featuring 3 separate rooms (400 sq. ft.): Bedroom with...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Captain John Stephens House is a stylish and sparkling, newly remodeled studio condominium unit located in the heart of Gloucester. There are 4 units in this building and Unit 3 is on the ground floor. This bright and modern studio makes a perfect summer vacation home for an individual or couple...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Waterfront
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    • Ocean Views
    • Washer
    • Grill
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    Pet friendly
    Kid 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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Remodeled 3BR Gloucester Annisquam River Cottage1 / 24
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We walked to the beach at Good Harbor and enjoyed crossing the sandbar at low tide to Salt Island. Two grocery stores, liquor store were very close. Gloucester had a small...
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    About this property
    Enjoy a peaceful retreat in coastal New England by staying at this lovely 3-bedroom, 1-bathroom Gloucester vacation rental cottage, which sleeps 6! Featuring a bright and welcoming interior, splendid waterfront views and terrific access to nearby beaches, this residence will surely become a place...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront 2 Bedroom !1 / 14
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Internet Access
    • Waterfront
    • Air Conditioning
    • Balcony
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    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2017
    This apartment is located on the water. When I say "on the water", that's exactly what I mean. At high tide, looking down from the balcony you see water. There are...
    Reviewed 25 June 2016
    All you would want, comfort, convience, excitement, and beauty. You cannot miss here. The view is spectacular.
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    About this property
    Vacation at the very edge of the Gloucester Inner Harbor watching the boats and ships passing by. Relax on your private deck over the water and enjoy this extraordinary picturesque setting that can't be matched anywhere on the harbor ! Whale watching or trips around harbor by boat is all within...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New in 2017! A riverfront property on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets you will experience from the deck or the delightful gazebo. This home has a brand new custom kitchen,...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Smoking allowed
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Front row seats from every room and deck to view glorious evening sunsets over the Annisquam River and Ipswich Bay. Sunset Cottage is a charming 2 bedroom, 1 bath cottage on Gloucester’s Thurston Point that sits directly on the tidal Annisquam River and boasts unparalleled views. Two decks with...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Vintage Home directly on the Annisquam River1 / 12
    (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
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 6 Bedrooms, Sleeps 12
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Waterfront
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate vacation home provides endless delights, both inside and out. This sunny and welcoming home is situated at the water's edge of the cove and offers three large bedrooms and 3 full baths as well as a lovely eat-in kitchen, formal dining and...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom Spectacular Views of Good Harbor Beach1 / 9
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Patio
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • DVD Player
    • Patio
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    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Satellite TV
    • Internet Access
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    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”...
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    Location Information
    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Porch
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    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable recently renovated 3 BR vacation home is conveniently located a block away from Gloucester's scenic outer harbor. You'll love being just steps away from Gloucester's historic Stage Fort Park, once a landing place for pirates, now home to two public beaches, tennis courts, newly...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Victorian House: Explore Rocky Neck's art galleries & restaurants1 / 37
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This is a great house, extremely comfortable and lovingly maintained by the owner. We were lucky enough to be guests during Autumn so the trees in the area had their season's...
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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....
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    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Satellite TV
    • Patio
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 3, this beach house is the perfect arrangement for couples and small families. Just step out the door, walk over the Good...
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    Gloucester, Cape Ann 01930
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    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
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Annie's Place: Sweet cottage just 0.2 miles to Plum Cove Beach1 / 17
    (1)Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    Gloucester, Cape Ann 01930
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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