Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Salem
Located in Salem, this vacation home is by the sea, within a 5-minute walk of Salem Maritime National Historic Site and New England Pirate Museum.
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
Located in Gloucester, this vacation home is by the sea, a 3-minute walk from Plum Cove Beach and within a 5-minute drive of Halibut Point State Park.
Beach Life Bliss - steps to the beach
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Swampscott
With a stay at this vacation home in Swampscott, you'll be within a 5-minute drive of Salem Harbor and Salem State College.
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
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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, within a 5-minute walk of Marblehead Museum & Historical Society and King Hooper Mansion.
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Salem
A stay at this vacation home places you in the heart of Salem, steps from Salem Witch Trials Memorial and New England Pirate Museum.
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
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$740 per night from 23 Jan to 24 Jan
AU$740
includes taxes & fees
23 Jan - 24 Jan
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
Wonderful home sitting right between two terrific beaches!

Wonderful home sitting right between two terrific beaches!

Gloucester
Located in Gloucester, this vacation home is by the sea, within a 5-minute drive of Good Harbor Beach and Cape Hedge Beach.
Wonderful home sitting right between two terrific beaches!
"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
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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
430 Holiday Homes
Lowest Price
AU$340
Highest Price
AU$740
Popular accommodation
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Beach Life Bliss - steps to the beach, Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace, OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi, Wonderful home sitting right between two terrific beaches!, "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

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$340 per night from 23 Jan to 24 Jan
AU$340
includes taxes & fees
23 Jan - 24 Jan
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
Located in Gloucester, The Hotel at Cape Ann Marina is a 4-minute drive from Hammond Castle and 10 minutes from Wingaersheek 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.