Gloucester Vacation Rentals

Compare 6 vacation rentals.
USA > Massachusetts > Gloucester

Make Gloucester your next getaway

With a Gloucester vacation rental, you have a front-row seat to most scenic small coastal towns that make up the heart of New England. This small fishing town rests along the eastern end of Cape Ann, near the larger town of Rockport and about 40 miles from the city of Boston. Experience beachside bliss and relaxation on your next trip to Massachusetts.

Explore Gloucester house rentals, cottages, guest houses, and more


House rentals

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Guest houses

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Gloucester vacation rentals for every getaway

Dog-friendly Hot tub Internet
Haskell Street Hideaway
3 Bedroom | 1.5 Bath | Sleeps 7 (6 Adults Max)

Haskell Street Hideaway - Gloucester, MA

$219 avg / night
Bianca's House
2 Bedroom | 1 Bath | Sleeps 4

Bianca's House - Gloucester, MA

$218 avg / night
Magnolia Tides
3 Bedroom | 3 Bath | Sleeps 6

Magnolia Tides - Gloucester, MA

$873 avg / night
Beau's Beach House
3 Bedroom | 2.5 Bath | Sleeps 6

Beau's Beach House - Gloucester, MA

$263 avg / night
Point Radio Cottage
0 Bedroom | 1.5 Bath | Sleeps 4 (2 Adults Max)

Point Radio Cottage - Gloucester, MA

$327 avg / night

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Recent Gloucester vacation rental reviews

The house was very clean and had a well stocked kitchen and plenty of towels. It had nice amenities if traveling with very small children. Located close to grocery stores and places to eat. Many restaurants close by 8 but the food is delicious. Short drive to Salem and Boston. Would definitely stay again.
Serena S. | Apr 2024
Clean and convenient location
Margaret B. | Mar 2024
This location was perfect for why we needed to be The home was clean and set up nicely. Everything we needed was available - we were all comfortable there, and the parking was great for both of our trucks. No issues with check in, check out or communication. Almost felt like we're were on vacation!
Christina R. | Mar 2024
Gloucester vacation rental FAQ

Yes, 10 of our Gloucester homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 31 of our Gloucester vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Gloucester vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Gloucester team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Gloucester, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Explore our Gloucester, MA, vacation rentals

Feel right at home on your trip to Cape Cod with Gloucester vacation rentals. With an active commercial fish pier, a historic downtown area, and amazing seafood, this welcoming town offers plenty of New England charm. Spend the day exploring the local museums and memorials, learning about the town's rich history, and head back to your vacation rental to enjoy some delicious fresh lobster or oysters. 

Things to do in Gloucester, MA

Between a bike ride along the shore and kicking your feet up to watch the waves come in, there’s no shortage of things to do near Gloucester. 

History of Gloucester, MA

With a history dating back to 1623, the town we know as Gloucester (pronounced "gloster") has a long and interesting background. The area was originally founded at Cape Ann by a group of settlers from Dorchester, England, predating both Salem and the city of Boston.

Since many original settlers moved to Salem in hopes of finding better farmland, the area of Gloucester was briefly abandoned before slowly coming back on the map again in the late 1600s. Today, you can see a variety of local sights near your vacation rental to explore the town's history, from the Town Green where settlers built the first school, to the White-Ellery House built in 1710 for Gloucester's first minister.