Gloucester Vacation Rentals

Compare 10 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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Popular amenities for Gloucester vacation rentals

Popular
Dog-friendly Hot tub Internet
Little River Retreat
2 Bedroom | 1.5 Bath | Sleeps 4

Little River Retreat - Gloucester, MA

$337 avg / night
(excludes fees and taxes)
Bianca's House
2 Bedroom | 1 Bath | Sleeps 4

Bianca's House - Gloucester, MA

$246 avg / night
(excludes fees and taxes)
3.83 (12)
Point Radio Cottage
0 Bedroom | 1.5 Bath | Sleeps 4 (2 Adults Max)

Point Radio Cottage - Gloucester, MA

$382 avg / night
(excludes fees and taxes)
4.79 (48)
Longview House
4 Bedroom | 2.5 Bath | Sleeps 7

Longview House - Gloucester, MA

$347 avg / night
(excludes fees and taxes)
4.67 (3)
Haskell Street Hideaway
3 Bedroom | 1.5 Bath | Sleeps 7 (6 Adults Max)

Haskell Street Hideaway - Gloucester, MA

$252 avg / night
(excludes fees and taxes)
4.73 (41)

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Recent Gloucester guest reviews

Quaint home in great location to events and restaurants. Downtown only 1/4 Mike walk and safe neighborhood
Ronald S. | Jun 2025
This beautiful apartment is exactly as shown. Great location, parking, easy access, extremely comfortable, clean and has all the amenities including a washer and dryer. Location is outstanding; very walkable, with great coffee shops, restaurants, shops, bookstores and the harbor and Boulevard close by. Wish we could have stayed longer and will definitely stay there again.
Timothy F. | Jun 2025
This house is everything you picture when you think New England vacation. Beautifully decorated, comfortable beds, ample eating space, and a cozy family room. My sister and I stayed here with our four kids and had a wonderful time. We loved walking to the water, exploring the rocks, enjoying lobster rolls on the beach. Great restaurants within walking distance -- and ice cream shop as well.
Kerstin L. | Jun 2025
Gloucester vacation rental FAQ

Yes. 32 of our Gloucester vacation rentals have internet access, so you can stay connected throughout your trip.

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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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Gloucester, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons 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.