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Vacation Rentals and House Rentals in Gloucester, MA

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    All 30 Rentals in Gloucester
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    Travelers to Gloucester are booking June dates now. Secure your vacation rental today, and have the perfect trip.
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    $325
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    1 / 28
    5 of 5 stars (2) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    4 of 5 stars (4) Very good
    4 Bedrooms / 7 Bathrooms / Sleeps 8
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    5 Bedrooms / 3 Bathrooms / Sleeps 11
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    1 Bedroom / 1 Bathroom / Sleeps 2
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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, queen 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
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    $90
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    1 / 9
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • ?
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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 main street so busy during the day, but close to everything by foot or bicycle. Sunny, furnished, adorable 1BD. Living Room/Kitchenette downstairs, Bedroom/Bath upstairs. Nestled... View all property information
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    Gloucester, Cape Ann 01930
    4 of 5 stars Reviewed August 15, 2014
    Recommend it to couples only, quaint, very clean cottage in a busy area. Take caution pulling out of driveway. Bathroom upstairs a little small not much head room for those over...
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    1 / 19
    5 Bedrooms / 2 Bathrooms / Sleeps 13
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    About this property
    **There is a possibility that construction will ongoing next door during the summer of 2015** 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 well as two... View all property information
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    Gloucester, Cape Ann 01930
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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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
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • x
    • ?
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    • x
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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
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    1 / 43
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Internet Access
    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    Lovely cottage set high up on a hill overlooking the private section of Wingaersheek Beach, this lovingly restored 3 bedroom home has been in the same family for over 55 years. The cottage boasts one of the most spectacular hilltop views on the entire beach with meticulously maintained lawn and... View all property information
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    Gloucester, Cape Ann 02116
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Internet Access
    • Private Fishing...
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    • Suitable for children
    • x
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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... View all property information
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    Gloucester, Cape Ann 01930
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Awesome East Gloucester house with picture perfect view! Sip cocktails and watch the boats go by. Walk to Rocky Neck for great dining, art galleries, and more. Enjoy the music from the Neck while sitting on your own deck. A short walk to Niles Beach, bring your bikes or running shoes and run or... View all property information
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    Gloucester, Cape Ann 01930
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    $12
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    Title Travelers see this first while they are browsing properties, so be sure your title stands out. Description Give travelers an idea of what to expect from a stay in your rental. What is the space like? What's nearby? What makes it special? Give travelers an idea of what to expect from a stay... View all property information
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    Gloucester, Cape Ann 01930
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    $1,400
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    1 / 26
    5 of 5 stars (10) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Picture a romantic, seaside cottage with a lovely large deck, set on a hillside overlooking the harbor... catching the summer wind, salt air and sounds of seagulls as they drift up from the harbor. Open living space - large living room with sliding door onto large private deck overlooking the... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed September 2, 2013
    Have just spent a week at the cottage and it was was absolutely lovely. It is exactly like the pictures, beautifully decorated and very well equipped. The owners, Linda and Hank...
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    $1,500
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    1 / 29
    5 of 5 stars (10) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This oceanfront year round home was recently constructed to maximize spectacular ocean views and sunsets. Enjoy the views of the water outside while sitting on the glassed in balcony just off of the master bedrooms , the screen/glass windows across the front or on the stone patio or dock. Inside,... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed October 2, 2012
    We were two families (four adults, 3 children and a toddler), and everyone had a wonderful time. Wingarsheek and Crane Beaches are reasonably convenient, as are some great...
    5 of 5 stars Reviewed May 1, 2012
    We were eight women celebrating over 50 years of friendship with a long weekend getaway. We were delighted with The Landry Cottage. The spacious house is brightly and...
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    $285
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    1 / 52
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    NEW IN 2013: Addition of new windows, insulation, Heat & Central Air Conditioning now extends our season March 1 – December 31.This newly renovated and updated waterfront gem has four bedrooms and 1.5 baths, a deep-water dock (accommodates up to a 20 foot boat) and a wrap-around screened porch... View all property information
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    Gloucester, Cape Ann 01930
    5 of 5 stars Reviewed February 3, 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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    $650
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    1 / 31
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Just 10 yards from the white sands and lively surf of Long Beach, this condo sleeps 10+ in centrally air conditioned comfort and offers 4 floors of living space with 3+ bedrooms and 2.5 baths. The aptly named beach is one mile long spanning both the community of Gloucester and Rockport - take your... View all property information
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    Gloucester, Cape Ann 01930
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    $220
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Located just a lane away from Gloucester's iconic Stacey Boulevard, this 3 bedroom/1.5 bath gem is steps away from the harbor, two beaches, glorious Stage Fort Park and the vibrant downtown with a huge array of restaurants, galleries, shops, museums and historic places of worship. Located on a... View all property information
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    Gloucester, Cape Ann 01930
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    $235
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacey 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
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    $390
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    1 / 21
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • x
    • x
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    About this property
    Walk to Gloucester's best beach - Good Harbor, located just 0.2 miles from this wonderful duplex, which offers three air conditioned bedrooms and two full custom tile baths with showers. Enter into the open concept living, dining and kitchen areas complete with parquet floors, which make the... View all property information
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    Gloucester, Cape Ann 01930
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    1 / 30
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Pets allowed
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    • x
    • x
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    • Elder access
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    About this property
    This well appointed 3 bedroom/ 2 bath pied a'terre is perched above the picturesque waterfront Stacey Boulevard which is one of the most scenic spots on all of Cape Ann- best known for the iconic Man-at-the-Wheel sculpture of the Gloucester Fisherman facing the elements of the sea depicting 'Those... View all property information
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    Gloucester, Cape Ann 01930
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    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    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 house has been in the same family since the 1880's. From the side entrance on a quiet lane, you will step into a bright back hall with full bath and... View all property information
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    Gloucester, Cape Ann 01930
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    $210
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    1 / 10
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
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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 apartment. Both the living room and the master bedroom have sliding doors that open onto a spacious, private, sun-kissed deck complete... View all property information
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    Gloucester, Cape Ann 01930
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    $380
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    1 / 32
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    About this property
    Direct waterfront on picturesque Goose Cove, this immaculate property 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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    $5,500
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    1 / 30
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Dishwasher
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    • Hot Tub
    • Internet Access
    • Satellite TV
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    Location, location, location! Waterviews & walk to Good Harbor Beach. This four bedroom/2.5 bath 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 popular beach and also... View all property information
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    Gloucester, Cape Ann 01930
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    $220
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    1 / 17
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
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    • Pets allowed
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    • x
    • ?
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    • ?
    • ?
    About this property
    A delightful home situated in Gloucester's charming Bay View neighborhood, Annies Place radiates an aura of sun and warmth. Only an 8 minute walk to lovely Plum Cove Beach, Annies Place lets you spend your summer vacation relaxing, discovering local fauna such as hermit crabs, and swimming to your... View all property information
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    Gloucester, Cape Ann 01930
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    $314
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    1 / 6
    4 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • 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
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    $279
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    1 / 9
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • 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
    From
    $1,714
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    1 / 51
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    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
    From
    $6,600
    / Week
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    1 / 35
    3 Bedrooms / 5 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    RENTING FOR AUGUST 2015. Ocean Whisper House is the high end, waterfront, air conditioned home you have been waiting for. The house has everything you could wish for with 3 ensuite bedrooms and 4.5 baths, AND it comes with a parking pass to park on Beach Street at Good Harbor Beach. Or if you... View all property information
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    Gloucester, Cape Ann 01930
    From
    $1,050
    / Night
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    1 / 50
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Sun when you want it. Shade when you need it. Cool Cove has it all. Jutting high above Wingaersheek Beach on a promontory from which it seems that you can see forever: Annisquam Lighthouse, Ipswich Bay, azure waters, pleasure boats, Walk from this four bedroom house, across a verdant lawn edged... View all property information
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    Location Information
    Gloucester, Cape Ann 01930