Vacation Rentals in Gloucester, MA
· House in Gloucester
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
6 Beds · 4 baths ·
Ski In Ski Out · Hot Tub · Hardwood Floor ·
From
$818/nightAmenities
Ski In Ski Out
Hot Tub
Hardwood Floor
Ocean
Fitness Center
Fireplace
Waterfront
On Site Laundry
Other spaces
Balcony, Kitchen
· House in Gloucester
Ocean View - Great Location | Beautiful, Warm & Spacious.
4 Beds · 3 baths · Sleeps 7 ·
Fitness Center · Workspace · Outdoor Space ·
From
$425/nightAmenities
Fitness Center
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in Gloucester
Plum Cove Beach House
2 Beds · 2 baths · Sleeps 6 ·
Workspace · On Site Laundry · Outdoor Space ·
From
$203/nightAmenities
On Site Laundry
Oven
Dishwasher
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Workspace, Kitchen
· Hotel in Gloucester
Romantic Retreat
1 Bed · Sleeps 4 ·
On Site Laundry · Outdoor Space · Oven ·
From
$144/nightAmenities
On Site Laundry
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
· Apartment in Gloucester
Gloucester Coastal Gem
3 Beds · 2 baths · Sleeps 6 ·
On Site Laundry · Outdoor Space · Oven ·
From
$140/nightAmenities
On Site Laundry
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Lovely 'Blue Heron Cottage' on Annisquam River!
3 Beds · 1 bath · Sleeps 6 ·
Microwave · Tv · Cable ·
From
$255/nightAmenities
Microwave
Tv
Cable
Assigned Parking
Ocean
Waterfront
Oven
Dishwasher
Other spaces
Kitchen
· House in Gloucester
Elegant Gloucester Beach Getaway with Ocean Views!
5 Beds · 2 baths · Sleeps 10 ·
Central Heat · Ceiling Fan · Tv ·
From
$750/nightAmenities
Central Heat
Ceiling Fan
Tv
Cable
Assigned Parking
Fireplace
Oven
Dishwasher
Other spaces
Kitchen
· Condo in Gloucester
DRIFT Accommodations, Perfect Location
2 Beds · 2 baths · Sleeps 6 ·
Balcony · Waterfront · Beach ·
From
$339/nightAmenities
Waterfront
Beach
Air Conditioning
In Unit Laundry
Furnished
Wifi
Residents Lounge
Other spaces
Balcony, Kitchen
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· Apartment in Gloucester
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
1 Bed · 1 bath · Sleeps 4 ·
Outdoor Space · Oven · Dishwasher ·
From
$104/nightAmenities
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
*NEW Antique Cottage|PRIVATE SAUNA|Beach|Trails
3 Beds · 2 baths · Sleeps 7 ·
Fitness Center · Workspace · Outdoor Space ·
From
$150/nightAmenities
Fitness Center
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Condo in Gloucester
The Duval House
2 Beds · 1 bath · Sleeps 6 ·
Oven · Air Conditioning · In Unit Laundry ·
From
$116/nightAmenities
Oven
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
*NEW Oceanside Village Home|Private Fenced Yard!
2 Beds · 2 baths · Sleeps 7 ·
Fitness Center · Workspace · Outdoor Space ·
From
$149/nightAmenities
Fitness Center
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Gloucester
Stanwood Point: Waterfront cottage with large screened porch, yard and dock
3 Beds · 2 baths · Sleeps 6 ·
Ocean · Fitness Center · Fireplace ·
From
$460/nightAmenities
Ocean
Fitness Center
Fireplace
Waterfront
Beach
Oven
Dishwasher
In Unit Laundry
Other spaces
Kitchen
· House in Gloucester
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
2 Beds · 3 baths · Sleeps 6 ·
Walk In Closets · Waterfront · Workspace ·
From
$303/nightAmenities
Walk In Closets
Waterfront
On Site Laundry
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in Gloucester
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
2 Beds · 1 bath · Sleeps 4 ·
Waterfront · Dishwasher · Air Conditioning ·
From
$181/nightAmenities
Waterfront
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Storage
Other spaces
Kitchen
· House in Gloucester
Helena House: European flair, close to Plum Cove Beach.
3 Beds · 2 baths · Sleeps 7 ·
Hardwood Floor · Balcony · Beach ·
From
$201/nightAmenities
Hardwood Floor
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Storage
Other spaces
Balcony, Kitchen
· House in Gloucester
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
3 Beds · 2 baths · Sleeps 7 ·
Waterfront · Dishwasher · Air Conditioning ·
From
$352/nightAmenities
Waterfront
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Jewel Box: A gem of a rental home close to Good Harbor Beach.
2 Beds · 1 bath · Sleeps 3 ·
Workspace · On Site Laundry · Beach ·
From
$198/nightAmenities
On Site Laundry
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Gloucester
COME STAY AT THE MERMAID COTTAGE ON LANES COVE !
1 Bed · 1 bath · Sleeps 3 ·
Ocean · Fitness Center · Waterfront ·
From
$200/nightAmenities
Ocean
Fitness Center
Waterfront
Beach
Oven
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
· House in Gloucester
Hidden Gem - 3 Minute Walk to Beach
3 Beds · 2 baths · Sleeps 7 ·
Ev Charging · Assigned Parking · Balcony ·
From
$360/nightAmenities
Ev Charging
Assigned Parking
Fireplace
On Site Laundry
Beach
Oven
Dishwasher
Air Conditioning
Other spaces
Balcony, Workspace, Kitchen
· House in Gloucester
Gorgeous New Home w/ Ocean Views- 2 Private Beaches Steps Away
4 Beds · 5 baths · Sleeps 8 ·
High Ceilings · Walk In Closets · Ocean ·
From
$510/nightAmenities
High Ceilings
Walk In Closets
Ocean
Waterfront
On Site Laundry
Beach
Oven
Dishwasher
Other spaces
Workspace, Kitchen
· House in Gloucester
Magnolia Tides: A gracious and luxurious multi-level waterfront home.
2 Beds · 3 baths · Sleeps 6 ·
Deck · Assigned Parking · Waterfront ·
From
$847/nightAmenities
Assigned Parking
Waterfront
On Site Laundry
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Deck, Workspace, Kitchen
· Apartment in Gloucester
Annisquam Bridge House at Lobster Cove. Booking fall/winter
2 Beds · 1 bath · Sleeps 4 ·
Deck · Oven · Air Conditioning ·
From
$227/nightAmenities
Oven
Air Conditioning
In Unit Laundry
Furnished
Residents Lounge
Other spaces
Deck, Kitchen
· House in Gloucester
The Haabah--4 min walk to Good Harbor Beach
2 Beds · 2 baths · Sleeps 8 ·
Assigned Parking · Fitness Center · Fireplace ·
From
$329/nightAmenities
Assigned Parking
Fitness Center
Fireplace
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
· Apartment in Gloucester
1886 Captains Carriage House Secluded Luxury Eastern Point Gloucester MA
3 Beds · 3 baths · Sleeps 10 ·
Ev Charging · Fireplace · Workspace ·
From
$990/nightAmenities
Ev Charging
Fireplace
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· House in Gloucester
Walk to Good Harbor Beach, pet friendly, family beach home
3 Beds · 2 baths · Sleeps 8 ·
Outdoor Space · Beach · Oven ·
From
$255/nightAmenities
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Residents Lounge
Other spaces
Kitchen
· House in Gloucester
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
3 Beds · 2 baths · Sleeps 9 ·
Ceiling Fan · On Site Laundry · Dishwasher ·
From
$278/nightAmenities
Ceiling Fan
On Site Laundry
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Grand Family Home Between Good Harbor and Long Beach
8 Beds · 2 baths · Sleeps 16 ·
Hardwood Floor · Fireplace · On Site Laundry ·
From
$686/nightAmenities
Hardwood Floor
Fireplace
On Site Laundry
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
· House in Gloucester
Wingaerchic: A hidden retreat near Gloucester's sandy Wingaersheek Beach.
3 Beds · 3 baths · Sleeps 6 ·
High Ceilings · Walk In Closets · Hardwood Floor ·
From
$307/nightAmenities
High Ceilings
Walk In Closets
Hardwood Floor
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
· House in Gloucester
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
2 Beds · 1 bath · Sleeps 4 ·
On Site Laundry · Beach · Dishwasher ·
From
$209/nightAmenities
On Site Laundry
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf; HiSpeed WiFi
2 Beds · 1 bath · Sleeps 4 ·
Hardwood Floor · Fireplace · Workspace ·
From
$257/nightAmenities
Hardwood Floor
Fireplace
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Workspace, Kitchen
· Apartment in Gloucester
Harbortown Hideaway: Charming home in downtown Gloucester with water views.
3 Beds · 2 baths · Sleeps 6 ·
Beach · Dishwasher · Air Conditioning ·
From
$291/nightAmenities
Beach
Dishwasher
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.
3 Beds · 2 baths · Sleeps 6 ·
Beach · Air Conditioning · In Unit Laundry ·
From
$297/nightAmenities
Beach
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
2 Beds · 1 bath · Sleeps 4 ·
Waterfront · On Site Laundry · Outdoor Space ·
From
$124/nightAmenities
Waterfront
On Site Laundry
Oven
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Take the A-Frame: Close to Wingaersheek Beach!
1 Bed · 1 bath · Sleeps 4 ·
Deck · Workspace · On Site Laundry ·
From
$288/nightAmenities
On Site Laundry
Beach
Dishwasher
In Unit Laundry
Furnished
Wifi
Other spaces
Deck, Workspace, Kitchen
· Apartment in Gloucester
Ocean and Woods! Best of both seaside delights in Gloucester!
2 Beds · 1 bath · Sleeps 4 ·
Outdoor Space · Beach · Oven ·
From
$175/nightAmenities
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Residents Lounge
Other spaces
Kitchen
· Apartment in Gloucester
♥ Pet Friendly|Memory Foam Bed|Minutes to Good Harbor+Rockport|Fast Wifi♥
3 Beds · 1 bath · Sleeps 6 ·
Beach · Oven · Air Conditioning ·
From
$196/nightAmenities
Beach
Oven
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· House in Gloucester
Seaside Escape just steps to Good Harbor beach in Gloucester
2 Beds · 1 bath · Sleeps 5 ·
High Ceilings · Fitness Center · Outdoor Space ·
From
$300/nightAmenities
High Ceilings
Fitness Center
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
· Apartment in Gloucester
Summer Cottage on Ipswich Bay
4 Beds · 3 baths · Sleeps 8 ·
Ocean · Waterfront · On Site Laundry ·
From
$515/nightAmenities
Ocean
Waterfront
On Site Laundry
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen
· House in Gloucester
Waterfront Wingaersheek Beach Unobstructed Panoramic Ocean and Lighthouse Views
4 Beds · 3 baths · Sleeps 8 ·
Ocean · Fitness Center · Waterfront ·
From
$723/nightAmenities
Ocean
Fitness Center
Waterfront
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
· Apartment in Gloucester
2 Bedroom Waterfront Unit, Vacation or Short Term Rental
2 Beds · 1 bath · Sleeps 4 ·
Hardwood Floor · Balcony · Waterfront ·
From
$315/nightAmenities
Hardwood Floor
Waterfront
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Workspace, Kitchen
· Apartment in Gloucester
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
1 Bed · 1 bath ·
In Unit Laundry · Air Conditioning · Furnished ·
From
$103/nightAmenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
· House in Gloucester
Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!
3 Beds · 1 bath · Sleeps 6 ·
Workspace · Outdoor Space · Beach ·
From
$275/nightAmenities
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Residents Lounge
Other spaces
Workspace, Kitchen
· Apartment in Gloucester
Walk to Good Harbor Beach 6/10 mile. Disc. rate 1/1 to 5/31 stays of 4+ wks
1 Bed · 1 bath · Sleeps 4 ·
Fitness Center · Outdoor Space · Beach ·
From
$105/nightAmenities
Fitness Center
Beach
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
· Apartment in Gloucester
Walk to Good Harbor Beach and Downtown Gloucester
1 Bed · 1 bath · Sleeps 2 ·
Beach · Oven · Air Conditioning ·
From
$153/nightAmenities
Beach
Oven
Air Conditioning
In Unit Laundry
Furnished
Wifi
Residents Lounge
Other spaces
Kitchen
· Hotel in Gloucester
Point Radio Cottage
1 Bed · Sleeps 2 ·
Balcony · Ocean · Waterfront ·
From
$255/nightAmenities
Ocean
Waterfront
On Site Laundry
Oven
Dishwasher
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
· Hotel in Gloucester
Beauport Hotel Gloucester
1 Bed · Sleeps 4 ·
Pool · Smoking Allowed · Carpet ·
From
$199/nightAmenities
Pool
Smoking Allowed
Carpet
Free Parking
Assigned Parking
Ocean
Fireplace
Waterfront
Other spaces
Workspace
· House in Gloucester
Steps to Harbor, Park, Beach and Boardwalk
2 Beds · 2 baths · Sleeps 4 ·
Workspace · Outdoor Space · Oven ·
From
$379/nightAmenities
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Swimming Pool
Other spaces
Workspace, Kitchen
· House in Gloucester
Bell View: Private tennis court and an in-law suite.
6 Beds · 6 baths · Sleeps 16 ·
Balcony · Fireplace · Beach ·
From
$668/nightAmenities
Fireplace
Beach
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, Kitchen
· House in Gloucester
Walk To Good Harbor, OCEAN VIEWS, Open All Winter!
3 Beds · 2 baths · Sleeps 6 ·
Balcony · Oven · Dishwasher ·
From
$174/nightAmenities
Oven
Dishwasher
Air Conditioning
In Unit Laundry
Furnished
Wifi
Package Service
Other spaces
Balcony, Kitchen
Showing 1 - 50 of 139 results
Updated: March 9, 2023
Learn about vacation rentals in
Gloucester
Explore 141 vacation rentals near Gloucester, Massachusetts. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Gloucester, you can see photos of Gloucester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Gloucester vacation rentals in specific areas. Whether you’re looking for a Gloucester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Gloucester is $103 per night and the highest price is $990 per night.
33 of the vacation rentals near Gloucester are
apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation
units is $178 per night. There are
currently 11 vacation units under this
price. 93 of the vacation rentals near Gloucester are houses.
The average bathroom count for a vacation house near Gloucester is
2. The average price for vacation houses near Gloucester is $360 per night. There are 51 vacation homes under this price. The most common
amenities for vacation rentals near Gloucester are: furnished, wifi, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
22 available
2 bed rentals
37 available
3 bed rentals
44 available
4+ bed rentals
35 available
Getting around Gloucester
Pedestrian friendly
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car friendly
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit friendly
3/10
There are a few mass transit options within the area.
Points of interest in Gloucester
Groceries
3/10
No grocery stores within walking distance
Shopping
3/10
Some shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Parks
9/10
Large amount of park space nearby
Nightlife
1/10
Few or no bars within walking distance
Vacation Rentals in Gloucester, MA FAQ
How many vacation rentals in Gloucester are available?
There are currently 141 vacation rentals in Gloucester available. Our vacation rentals in Gloucester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Gloucester?
Yes, right now there are 30 pet friendly vacation rentals in Gloucester. A pet friendly vacation rental in Gloucester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Gloucester with a pool?
Yes there are vacation rentals with a pool available in Gloucester, MA. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Gloucester with internet access?
As of March 9, 2023, there are vacation rentals with internet access available in Gloucester, Massachusetts. Check out more enjoyable destinations on Vacations by Zumper.
