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Gloucester Vacation Rentals

19 Gloucester Vacation Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Gloucester, Eastern, Massachusetts, United States.
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Listings 1 - 19 of 19


3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: Helena House: Bright & cheery home just 0.7 miles from Plum Cove Beach! This delightful 3 bedroom, 1.5 bath Queen Anne style home is bright and ch...
Rates
$235 - $267 night
$1250 - $1960 week


Pet Friendly   Non Smoking


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3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: Captains Watch: 1 block to waterfront Boulevard & downtown. 3 beds/1.5 baths Located just a lane away from Gloucester's iconic Stacey Boulevard, t...
Rates
$220 - $275 night
$1150 - $1855 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Home in Gloucester
Home: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States
Description: Paradise Point: Direct Waterfront with deepwater dock & sunsets Direct waterfront with a deep water dock perfect for boating, swimming or just rel...
Rates
$500 - $550 night
$2500 - $4130 week


Non Smoking


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5 bedroom Vacation Rental Home in Gloucester
Home: 5 Bedroom, 2 Bathroom, Sleeps 9
Location: Gloucester, Massachusetts, United States
Description: Located above the western shore of Gloucester?s historic harbor and lovingly renovated in 2011, this beautiful and spacious five bedroom Victorian ...
Rates
$420 - $495 night
$2200 - $3500 week


Non Smoking


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3 bedroom Vacation Rental Condo in Gloucester
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States
Description: Walk to Gloucester's best beach - Good Harbor, located just 0.2 miles from this wonderful duplex, which offers three air conditioned bedrooms and t...
Rates
$390 - $390 night
$2750 - $3255 week


Non Smoking


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1 bedroom Vacation Rental Apartment in Gloucester
Apartment: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Gloucester, Massachusetts, United States
Description: Art Haven: Direct waterfront with large deck and dock! One month minimum. Located in Gloucester?s Rocky Neck Cultural District, this charming one ...
Rates
$933 - $1250 week


Non Smoking


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1 bedroom Vacation Rental Apartment in Gloucester
Apartment: 1 Bedroom, 1 Bathroom, Sleeps 3
Location: Gloucester, Massachusetts, United States
Description: Good Harbor Beach! Friday to Friday rental! Step out the door, walk over the Good Harbor Beach footbridge and you are on one of Gloucester?s most h...
Rates
$1275 - $1384 week


Non Smoking


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2 bedroom Vacation Rental Cottage in Gloucester
Cottage: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: Water's Edge Too: Direct waterfront on the banks of picturesque Goose Cove Featuring a waterfront location, 2 bedrooms, 2 baths, and the option to...
Rates
$200 - $200 night
$1350 - $1610 week


Pet Friendly   Non Smoking


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3 bedroom Vacation Rental Apartment in Gloucester
Apartment: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States
Description: 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 spo...
Rates
$350 - $450 night
$1650 - $2420 week


Non Smoking


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2 bedroom Vacation Rental Condo in Gloucester
Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Gloucester, Massachusetts, United States
Description: Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacey Boulevard is home to the icon...
Rates
$235 - $259 night
$1300 - $1792 week


Pet Friendly   Non Smoking


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4 bedroom Vacation Rental Home in Gloucester
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States
Description: This bright and open contemporary home was custom designed and built by the architect owner. The care and skill is reflected in the soaring ceiling...
Rates
$440 - $480 night
$2325 - $3675 week


Non Smoking


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3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: Days' End: 3Br in idyllic & private area in East Gloucester; 1 mile to beach! This lovely three bedroom/ two bath Victorian brings you back to an ...
Rates
$1950 - $2145 week


Non Smoking


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3 bedroom Vacation Rental Cottage in Gloucester
Cottage: 3 Bedroom, 3.5 Bathroom, Sleeps 7
Location: Gloucester, Massachusetts, United States
Description: Enjoy the views of the sparkling waters of the Annisquam River and Ipswich Bay beyond as well as Wingarsheek Beach and the Annisqaum Yacht Club jus...
Rates
$400 - $495 night
$2100 - $3360 week


Non Smoking


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3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 1 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: 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 t...
Rates
$220 - $275 night
$1150 - $1855 week


Pet Friendly   Non Smoking


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4 bedroom Vacation Rental Home in Gloucester
Home: 4 Bedroom, 2 Bathroom, Sleeps 10
Location: Gloucester, Massachusetts, United States
Description: This delightful and charming home is ideally situated just one block from Good Harbor Beach overlooking the sand and the surf. Four bedrooms and tw...
Rates
$565 - $565 night
$3500 - $4725 week


Non Smoking


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2 bedroom Vacation Rental Apartment in Gloucester
Apartment: 2 Bedroom, 1 Bathroom, Sleeps 3
Location: Gloucester, Massachusetts, United States
Description: Griffin's Getaway: Sweet 2 BR apartment with views of Ipswich Bay! This sweet two bedroom apartment has views of Ipswich Bay from its second floor...
Rates
$150 - $165 night
$600 - $661 week


Non Smoking


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3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Gloucester, Massachusetts, United States
Description: Direct waterfront on picturesque Goose Cove, this immaculate property provides endless delights, both inside and out. This sunny and welcoming hom...
Rates
$380 - $440 night
$2000 - $3150 week


Pet Friendly   Non Smoking


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3 bedroom Vacation Rental Home in Gloucester
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Gloucester, Massachusetts, United States
Description: Victorian House: Gorgeous home on Rocky Neck and just 0.2 miles to beach. Tastefully renovated, Victorian House on Rocky Neck, Gloucester?s fabled...
Rates
$286 - $286 night
$2000 - $3025 week


Non Smoking


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3 bedroom Vacation Rental Condo in Gloucester
Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 10
Location: Gloucester, Massachusetts, United States
Description: Long Beach Condo -Steps from the white sand and surf, sleeps 10+,central A/C Just 10 yards from the white sands and lively surf of Long Beach, thi...
Rates
$465 - $693 night
$2450 - $3850 week


Non Smoking


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Listings 1 - 19 of 19

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