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Gloucester Vacation Rentals

Browse 740 available vacation homes and compared across 9 trusted partners

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Top-Rated Vacation rentals in Gloucester

Book the highest-rated Gloucester vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Apartment Gloucester

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

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House Gloucester

Sunset Views, Waterfront Property, Dock - Sleeps 12

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House Gloucester

Vacation home with barbecue, garden & patio

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House Gloucester

Waterfront Home with Spectacular Viewsof the Annisquam River

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House Gloucester

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

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House Gloucester

House with BBQ & terrace

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House Gloucester

PREMIUM Modern Home on 2 Acres - Panoramic Marsh Views - NEW Video Tour

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House Gloucester

Vacation home with patio, barbecue & hot tub

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House Gloucester

Vacation home with barbeque, terrace & yard

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House Gloucester

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

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Apartment Gloucester

Oceanfront Rockport Getaway with Loft & Views

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House Gloucester

Family home – top 2 floors. Minutes walk to town and beach

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Apartment Gloucester

Quiet Cozy Apt Minutes from the Beaches and Shops!

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House Gloucester

Long Beach Gloucester. 1 minute walk to Beach. Large yard, lush gardens. 1 pup ok

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House Gloucester

Clean Waterfront Classic Cottage with Private Beach

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Top 15 most Recommended Vacation Rentals in Gloucester

Discover your ideal Gloucester vacation rental with real-time comparisons of 740 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Gloucester
House ∙ 8 guests ∙ 3 bedrooms

House with garden, patio & barbecue

Gloucester, Essex County, Massachusetts, United States
This house rental in Gloucester accommodates 8 guests and features a spacious yard perfect for outdoor activities.
from $430
per night
(85)
View deal
Apartment Gloucester
Apartment ∙ 4 guests ∙ 2 bedrooms

Fully equipped pleasant apartment with barbeque & terrace | Nature view | Close to the beach | Suitable for remote work

Gloucester, Essex County, Massachusetts, United States
Spacious apartment rental in Rockport for 4 featuring a modern kitchen and convenient parking.
from $120
per night
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Cabin Gloucester
Cabin ∙ 5 guests ∙ 2 bedrooms

Family-friendly cottage with patio, barbecue & yard | City view | Close to the beach | Pets are welcome

Gloucester, Essex County, Massachusetts, United States
This cozy cabin in Rockport accommodates 5 guests and features a family-friendly kitchen for enjoyable meals together.
from $247
per night
(52)
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House Gloucester
House ∙ 9 guests ∙ 4 bedrooms

Children-friendly beautiful house with terrace & barbeque | Nature view | Next to the beach | Pet-friendly

Gloucester, Essex County, Massachusetts, United States
This house rental in Rockport accommodates 9 guests and features beach access for a perfect family getaway.
from $631
per night
(53)
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House Gloucester
House ∙ 10 guests ∙ 5 bedrooms

House | Suitable for remote work

Gloucester, Essex County, Massachusetts, United States
This house rental in Gloucester accommodates 10 guests and features a fully equipped kitchen for convenient meal preparation.
from $277
per night
(76)
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House Gloucester
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with BBQ, yard & terrace | Perfect for remote work

Gloucester, Essex County, Massachusetts, United States
Charming house rental in Gloucester for 6 guests featuring a spacious yard and modern kitchen amenities.
from $324
per night
(10)
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Apartment Gloucester
Apartment ∙ 4 guests ∙ 2 bedrooms

Children-friendly apartment with garden | Beach nearby | Dogs allowed

Gloucester, Essex County, Massachusetts, United States
This family-friendly apartment rental in Gloucester accommodates 4 and features a fully equipped kitchen for your convenience.
from $180
per night
(1)
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House Gloucester
House ∙ 26 guests ∙ 11 bedrooms

Vacation home with hot tub, private pool & patio

Gloucester, Essex County, Massachusetts, United States
This house rental in Gloucester accommodates 26 guests and features a private pool for a perfect getaway.
from $2,157
per night
(9)
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House Gloucester
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with barbecue

Gloucester, Essex County, Massachusetts, United States
This house rental in Rockport accommodates 6 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $833
per night
(16)
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