Gloucester Vacation Rentals

Compare 9 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, apartments, cottages, and more

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House rentals

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Apartments

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Cottages

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Gloucester vacation rentals for every getaway

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

Haskell Street Hideaway - Gloucester, MA

$290 avg / night
4.69 (32)
Bianca's House
2 Bed | 1 Bath | Sleeps 4

Bianca's House - Gloucester, MA

$327 avg / night
3.82 (11)
Magnolia Tides
3 Bed | 3 Bath | Sleeps 6

Magnolia Tides - Gloucester, MA

$1,394 avg / night
5.0 (5)
Beau's Beach House
3 Bed | 2.5 Bath | Sleeps 6

Beau's Beach House - Gloucester, MA

$352 avg / night
4.85 (26)
Point Radio Cottage
0 Bed | 1.5 Bath | Sleeps 4 (2 Adults Max)

Point Radio Cottage - Gloucester, MA

$467 avg / night
4.77 (43)

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Recent Gloucester vacation rental reviews

It was a lovely and spacious place to stay during our first visit to Gloucester. We were there for a wedding and enjoyed spending our free time walking around the town. Every wedding event was within walking distance. We really enjoyed it!
Annie S. | Nov 2024
This was a great home (nice flip), centrally located for all the things we wanted to do. If it weren't so cold (haa, haa), we'd consider moving to Gloucester. Town was quaint and people were super friendly. Even had one of the locals recommend taking the commuter train into Salem on 10/31 instead of driving. Great tip. Would definitely stay again.
Kellie C. | Nov 2024
The location, though the train is in the backyard, was very convenient. As a coffee drinker, Dunkin was a couple min walk. My boyfriend and I planned this trip around going to Salem for halloween so having the train within walking distance was perfect. If you are a light sleeper, this may not be for you. But with that we were both so tired from exploring the beautiful city that we didn't notice too much. Definitely a great stay!
Sam H. | Nov 2024
Gloucester Frequently Asked Questions

Yes, 9 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. 35 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.