Vacation Rentals in Gloucester, MA

192 rentals

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Gloucester, MA

Book a vacation rental in Gloucester that has the highest visitor rating. Here are 6 of the best vacation rentals in Gloucester.
Walk to Good Harbor Beach. 3BR home, NEW Kitchen
10

Excellent

·
Gloucester
·
3 br
·
Sleeps 8
·
Outdoor Space · In Unit Laundry · Air Conditioning ·
From
$205/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Air Conditioning
Wifi
Dishwasher
Fireplace
Furnished
Residents Lounge
Oven
Other spaces
Outdoor Space, Kitchen
Amazing Waterfront/Access 4BDRM in Riggs Point
10

Excellent

·
Gloucester
·
4 br
·
Sleeps 8
·
Outdoor Space · Workspace · Air Conditioning ·
From
$399/night
Check availability
Property
Apartment · 4 Beds · 1 bath
Amenities
Air Conditioning
Waterfront
In Unit Laundry
Ocean
Fitness Center
Oven
Residents Lounge
Furnished
Other spaces
Outdoor Space, Workspace, Kitchen
Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach
10

Excellent

·
Gloucester
·
1 br
·
Sleeps 3
·
Residents Lounge · Deck · Workspace ·
From
$127/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Residents Lounge
Wheelchair Accessible
Air Conditioning
Wifi
Waterfront
Furnished
Beach
Assigned Parking
Other spaces
Deck, Workspace, Kitchen
Private Beach, Best Beach House in Gloucester!
10

Excellent

·
Gloucester
·
3 br
·
Sleeps 7
·
Oven · Air Conditioning · Wifi ·
From
$600/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Oven
Air Conditioning
Wifi
Furnished
Ocean
In Unit Laundry
Dishwasher
On Site Laundry
Other spaces
Kitchen, Balcony
Long Beach Suites: Book 2024 Summer Trip Today!
10

Excellent

·
Gloucester
·
2 br
·
Sleeps 6
·
In Unit Laundry · Wifi · Air Conditioning ·
From
$186/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
In Unit Laundry
Wifi
Air Conditioning
Oven
Furnished
Dishwasher
Other spaces
Kitchen
Elegant Gloucester Beach Getaway with Ocean Views!
9.9

Excellent

·
Gloucester
·
5 br
·
Sleeps 11
·
Wifi · Outdoor Space · Tv ·
From
$750/night
Check availability
Property
House · 5 Beds · 2 baths
Amenities
Wifi
Tv
Fireplace
On Site Laundry
Cable
Central Heat
Air Conditioning
Oven
Other spaces
Outdoor Space, Kitchen

Our Recommended Vacation Rentals in Gloucester, MA

We analyzed vacation rentals in Gloucester from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Gloucester to help you find a deal for your next trip.
Point Radio Cottage
9.5

Excellent

·
Gloucester
·
1 br
·
Sleeps 2
·
Kitchen · Waterfront · Swimming Pool ·
From
$314/night
Check availability
Property
Hotel · 1 Bed
Amenities
Waterfront
Swimming Pool
On Site Laundry
Dishwasher
Oven
In Unit Laundry
Furnished
Ocean
Other spaces
Kitchen, Balcony
Gloucester Coastal Gem
8.5

Very good

·
Gloucester
·
3 br
·
Sleeps 6
·
Air Conditioning · Fireplace · On Site Laundry ·
From
$225/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Air Conditioning
Fireplace
On Site Laundry
Oven
In Unit Laundry
Furnished
Swimming Pool
Dishwasher
Other spaces
Outdoor Space, Kitchen
Beau's Beach House
9.7

Excellent

·
Gloucester
·
3 br
·
Sleeps 6
·
Air Conditioning · On Site Laundry · Wifi ·
From
$311/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Air Conditioning
On Site Laundry
Wifi
Swimming Pool
In Unit Laundry
Dishwasher
Furnished
Oven
Other spaces
Outdoor Space, Workspace, Kitchen
Bianca's House

No rating

·
Gloucester
·
2 br
·
Sleeps 4
·
Kitchen · On Site Laundry · Oven ·
From
$227/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
On Site Laundry
Oven
Swimming Pool
Furnished
Wifi
Air Conditioning
Other spaces
Kitchen, Workspace, Outdoor Space
Walk To Good Harbor OCEAN VIEWS Open All Year

No rating

·
Gloucester
·
3 br
·
Sleeps 6
·
Free Parking · Oven · Air Conditioning ·
From
$383/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Free Parking
Oven
Air Conditioning
Dishwasher
Furnished
Wifi
Other spaces
Kitchen, Outdoor Space

Budget-Friendly Vacation Rentals in Gloucester, MA

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Gloucester starting at $88. Use the price filter at the top of the page to search for more specific prices.
Cozy & Elegant Winter Rental

No rating

·
Gloucester
·
2 br
·
Sleeps 2
·
Dishwasher · Wifi · Furnished ·
From
$88/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Dishwasher
Wifi
Furnished
Oven
In Unit Laundry
Hardwood Floor
Hot Tub
Air Conditioning
Other spaces
Kitchen
Water Front Cozy Cottage With amazing Sunset

No rating

·
Gloucester
·
1 br
·
Sleeps 2
·
Furnished · Air Conditioning · In Unit Laundry ·
From
$88/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Air Conditioning
In Unit Laundry
Wifi
Dishwasher
Oven
Other spaces
Kitchen
Steps to Harbor, Park, Beach and Boardwalk
10

Excellent

·
Gloucester
·
2 br
·
Sleeps 4
·
Swimming Pool · Furnished · Kitchen ·
From
$98/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Swimming Pool
Furnished
In Unit Laundry
Wifi
Dishwasher
Oven
Air Conditioning
Other spaces
Kitchen, Outdoor Space, Workspace
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
10

Excellent

·
Gloucester
·
1 br
·
Sleeps 4
·
Furnished · In Unit Laundry · Outdoor Space ·
From
$104/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Dishwasher
Wifi
Oven
Air Conditioning
Other spaces
Outdoor Space, Kitchen
Walk to the ocean, very private. Secluded, woodsy location.
10

Excellent

·
Gloucester
·
1 br
·
Sleeps 2
·
Kitchen · Workspace · Furnished ·
From
$105/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Fitness Center
Wifi
Other spaces
Kitchen, Workspace, Outdoor Space
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
10

Excellent

·
Gloucester
·
1 br
·
Sleeps 2
·
Furnished · Workspace · Wifi ·
From
$108/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Wifi
In Unit Laundry
Other spaces
Workspace, Outdoor Space

Vacation Rentals With A Pool in Gloucester, MA

Want to relax by the pool? Book one of these Gloucester vacation rentals with a pool.
Prime Gloucester Property Overlooking Inner Harbor
10

Excellent

·
Gloucester
·
2 br
·
Sleeps 6
·
Swimming Pool · In Unit Laundry · Oven ·
From
$213/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Swimming Pool
In Unit Laundry
Oven
Air Conditioning
Pool
Beach
Residents Lounge
Furnished
Other spaces
Kitchen, Outdoor Space
4 Bedroom LUX House/with Pool Next Door
10

Excellent

·
Gloucester
·
4 br
·
Sleeps 6
·
Air Conditioning · Oven · Dishwasher ·
From
$200/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Oven
Dishwasher
Lake
Pool
Furnished
Fireplace
Hot Tub
Other spaces
Kitchen, Outdoor Space
Stunning 2.300 sq ft sea view home; Avail again wkly in May and June 2024
10

Excellent

·
Gloucester
·
3 br
·
Sleeps 6
·
On Site Laundry · Fireplace · Furnished ·
From
$652/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Fireplace
Furnished
Oven
Dishwasher
Storage
Wifi
Waterfront
Other spaces
Balcony, Kitchen, Workspace
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Updated: February 23, 2024