Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Newburyport
The price is AU$728 per night from 1 Jan to 2 Jan
AU$728
includes taxes & fees
1 Jan - 2 Jan 2025
Located in Newburyport, this vacation home is by the sea, a 5-minute drive from Newbury Beach and 6 minutes from Plum Island Beach.
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
The widow’s walk your very own spa experience

The widow’s walk your very own spa experience

Marblehead
Located in Marblehead, this vacation home is on the waterfront, within a 5-minute drive of Marblehead Museum & Historical Society and Massachusetts Bay.
The widow’s walk your very own spa experience
OLD TOWN CHARM.  
Sleeps 4- 2 bedrooms - 2.5 baths

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Marblehead
Located in Marblehead, this vacation home is by the sea, a 3-minute walk from Marblehead Museum & Historical Society and within a 5-minute drive of Fort ...
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
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Stunning 2 bed apt in Revere 15 mins to Boston

Stunning 2 bed apt in Revere 15 mins to Boston

Revere
With a stay at this vacation home in Revere, you'll be within a 10-minute drive of TD Garden and Encore Boston Harbor.
Stunning 2 bed apt in Revere 15 mins to Boston
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Gloucester,
With a stay at this vacation home in Gloucester, you'll be on the waterfront, just a 2-minute walk from Rocky Neck Art Colony and 5 minutes by foot from Bryan ...
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

Manchester-by-the-Sea
Located in Manchester-by-the-Sea, this vacation home is by the ocean, a 4-minute drive from West Beach and 6 minutes from Singing Beach.
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

Gloucester
When you stay at this vacation home in Gloucester, you'll be by the sea, within a 5-minute drive of Fishermen's Memorial Monument and Stage Fort Park.
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem
A stay at this vacation home places you in the heart of Salem, within a 15-minute walk of Witch House and Witch Dungeon Museum.
Leslie's Retreat: Spacious home ideally located to everything
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Rockport
With a stay at this vacation home in Rockport, you'll be within a 10-minute walk of Shalin Liu Performance Center and Front Beach.
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!
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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
420 Holiday Homes
Lowest Price
AU$249
Highest Price
AU$728
Popular accommodation
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi, The widow’s walk your very own spa experience, OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths, Stunning 2 bed apt in Revere 15 mins to Boston, "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC, Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape! , Leslie's Retreat: Spacious home ideally located to everything, Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Top trending hotels in Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is AU$327 per night from 29 Dec to 30 Dec
AU$327
includes taxes & fees
29 Dec - 30 Dec
With a stay at Beauport Hotel Gloucester in Gloucester, you'll be on the beach, just a 3-minute walk from Massachusetts Bay and 5 minutes by foot from Pavilion ...
Beauport Hotel Gloucester
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
The price is AU$249 per night from 23 Dec to 24 Dec
AU$249
includes taxes & fees
23 Dec - 24 Dec
Located in Gloucester, The Hotel at Cape Ann Marina is a 4-minute drive from Hammond Castle and 10 minutes from Good Harbor Beach.
The Hotel at Cape Ann Marina
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
When you stay at The Vista in Gloucester, you'll be by the ocean, within a 5-minute drive of Good Harbor Beach and Schooner Adventure.
The Vista
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Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
Located in Gloucester, Castle Manor Inn is by the ocean, within a 5-minute drive of Stage Fort Park and Fishermen's Memorial Monument.
Castle Manor Inn
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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.