Gloucester Vacation Rentals - HolidayHomes base64Hash Gloucester Vacation Rentals - HolidayHomes

Gloucester Vacation Rentals

Browse 762 available vacation homes and compared across 10 trusted partners

Anytime
Guests
Anytime
Guests

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

House Gloucester
PREMIUM PROPERTY - Private 2-Acre Retreat - MODERN 4 Bedrooms - See Video Tour
Book now
House Gloucester
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Book now
House Gloucester
Ocean front and 3 beaches across, parks, short walk to historic downtown!
Book now
House Gloucester
Classic New England: Big Family Home; Spas Garden FirePit; walk to beach, shops.
Book now
House Gloucester
Long Beach/Gloucester. 1 minute walk to Beach! Large yard, lush gardens. Pup ok!
Book now
Apartment Gloucester
Oceanfront penthouse 2 bed 2 bath situated on beach and downtown
Book now
House Gloucester
Clean Waterfront Classic Cottage with Private Beach
Book now
House Gloucester
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
Book now
House Gloucester
House with garden, BBQ & patio | Suitable for remote work
Book now
House Gloucester
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Book now
House Gloucester
5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!
Book now
House Gloucester
Vacation home with BBQ
Book now
House Gloucester
Airstream & Ocean View: Unique Gloucester Getaway
Book now
Apartment Gloucester
Oceanview and downtown with direct beach access 1 Bed 1 Bath
Book now
House Gloucester
Newly Updated! Charming bungalow with pool! Walk to Front Beach and shops!
Book now

Top 15 most Recommended Vacation Rentals in Gloucester

Discover your ideal Gloucester vacation rental with real-time comparisons of 762 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Gloucester
House ∙ 14 guests ∙ 6 bedrooms

325 m² House

Gloucester, Essex County, Massachusetts, United States
This house rental in Rockport accommodates 14 guests and features a spacious yard perfect for family gatherings.
from $896
per night
(67)
View deal
Cabin Gloucester
Cabin ∙ 4 guests ∙ 2 bedrooms

83 m² Cabin

Gloucester, Essex County, Massachusetts, United States
Cozy cabin in Gloucester accommodating 4 guests, featuring a well-equipped kitchen for convenient meal preparation.
from $205
per night
(27)
View deal
House Gloucester
House ∙ 8 guests ∙ 3 bedrooms

103 m² House

Gloucester, Essex County, Massachusetts, United States
This house rental in Rockport accommodates 8 guests and features a family-friendly kitchen for convenient meal preparation.
from $195
per night
(37)
View deal
House Gloucester
6 guests ∙ 3 bedrooms

House

Gloucester, Essex County, Massachusetts, United States
Charming house rental in Rockport for 6 guests featuring a spacious kitchen and pet-friendly accommodations.
from $496
per night
View deal
House Gloucester
House ∙ 4 guests ∙ 2 bedrooms

88 m² House

Gloucester, Essex County, Massachusetts, United States
Cozy house rental in Gloucester accommodating 4 guests with a family-friendly kitchen perfect for home-cooked meals.
from $150
per night
(31)
View deal
House Gloucester
House ∙ 6 guests ∙ 3 bedrooms

139 m² House

Gloucester, Essex County, Massachusetts, United States
This charming house rental in Gloucester accommodates 6 guests and features a family-friendly kitchen and a spacious yard.
from $241
per night
(73)
View deal
House Gloucester
House ∙ 4 guests ∙ 2 bedrooms

64 m² House

Gloucester, Essex County, Massachusetts, United States
This house rental in Gloucester accommodates 4 guests and features a spacious yard for outdoor enjoyment.
from $234
per night
(3)
View deal
House Gloucester
House ∙ 7 guests ∙ 2 bedrooms

158 m² House

Gloucester, Essex County, Massachusetts, United States
This house rental in Gloucester accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $330
per night
(11)
View deal
Apartment Gloucester
4 guests ∙ 2 bedrooms

Apartment

Gloucester, Essex County, Massachusetts, United States
Cozy apartment rental in Gloucester for 4 with a family-friendly atmosphere and easy access to the waterfront.
from $371
per night
(8)
View deal

More travel options

image-tag