Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Downtown Salem retreat 3BD w/ parking

Downtown Salem retreat 3BD w/ parking

Salem, MA
With a stay at this vacation home in Salem, you'll be within a 15-minute walk of Salem Witch Museum and Salem Common.
Opens in a new windowDowntown Salem retreat 3BD w/ parking
Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC

Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC

Newburyport
Located in Newburyport, this vacation home is by the ocean, within a 10-minute drive of Parker River National Wildlife Refuge and Joppa Flats Education Center ...
Opens in a new windowSunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Hampton
The price is AU$959 per night from 1 Dec to 2 Dec
AU$959
1 Dec - 2 Dec
includes taxes & fees
A stay at this vacation home places you in the heart of Hampton, within a 10-minute walk of Hampton Beach and Ocean Gaming Casino.
Opens in a new windowPremier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
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Coastal Retreat: steps to beach and town

Coastal Retreat: steps to beach and town

Swampscott
With a stay at this vacation home in Swampscott, you'll be within a 15-minute drive of Salem Witch Museum and Revere Beach.
Opens in a new windowCoastal Retreat: steps to beach and town
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem
With a stay at this vacation home, you'll be centrally located in Salem, within a 5-minute drive of Salem Witch Museum and Witch House.
Opens in a new windowLeslie's Retreat: Spacious home ideally located to everything
Classic New England Bunkhouse- Home for the whole family!

Classic New England Bunkhouse- Home for the whole family!

Haverhill
The price is AU$547 per night from 9 Nov to 10 Nov
AU$547
9 Nov - 10 Nov
includes taxes & fees
With a stay at this vacation home in Haverhill, you'll be within a 5-minute drive of Bradford Country Club and Ski Bradford.
Opens in a new windowClassic New England Bunkhouse- Home for the whole family!
Delightful 4-bedroom house with AC in charming Essex

Delightful 4-bedroom house with AC in charming Essex

Essex, MA
A stay at this vacation home places you in the heart of Essex, a 1-minute drive from Essex River and 6 minutes from Agassiz Rock.
Opens in a new windowDelightful 4-bedroom house with AC in charming Essex
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2 out of 5
Salem
The price is AU$732 per night from 12 Nov to 13 Nov
AU$732
12 Nov - 13 Nov
includes taxes & fees
This vacation home is in the heart of Salem, within a 10-minute walk of House of the Seven Gables and Salem Witch Museum.
Opens in a new windowEntire 4BR 2 Bath Home l Minutes to Downtown Salem
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Gloucester
With a stay at this vacation home in Gloucester, you'll be within a 10-minute drive of Good Harbor Beach and Cape Ann.
Opens in a new windowCranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Gloucester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gloucester vacation homes are the perfect way for you to wing it.

Holiday houses in Gloucester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gloucester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gloucester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gloucester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gloucester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gloucester Holiday Homes essential information

Accommodation
548 Holiday Homes
Lowest Price
AU$547
Highest Price
AU$959
Popular accommodation
Downtown Salem retreat 3BD w/ parking, Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC, Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Coastal Retreat: steps to beach and town, Leslie's Retreat: Spacious home ideally located to everything, Classic New England Bunkhouse- Home for the whole family!, Delightful 4-bedroom house with AC in charming Essex, Entire 4BR 2 Bath Home l Minutes to Downtown Salem, Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Top trending hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
When you stay at Castle Manor Inn in Gloucester, you'll be by the ocean, within a 15-minute drive of Wingaersheek Beach and Good Harbor Beach.
Opens in a new windowCastle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
Located in Gloucester, Ocean House Hotel at Bass Rocks is by the ocean, within a 5-minute drive of Good Harbor Beach and Maritime Gloucester.
Opens in a new windowOcean House Hotel at Bass Rocks
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
When you stay at Beauport Hotel Gloucester in Gloucester, you'll be on the beach, within a 10-minute drive of Good Harbor Beach and Cape Ann.
Opens in a new windowBeauport Hotel Gloucester
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Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
When you stay at Sea Lion Motel and Cottages in Gloucester, you'll be near the beach, a 2-minute drive from Good Harbor Beach and 7 minutes from Cape Ann.
Opens in a new windowSea Lion Motel and Cottages
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.