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
The price is AU$694 per night from 23 Mar to 24 Mar
AU$694
includes taxes & fees
23 Mar - 24 Mar
When you stay at this vacation home in Salem, you'll be by the sea, within a 10-minute walk of Salem Witch Museum and Salem Custom House.
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 10-minute drive of Salem Witch Museum and Salem Harbor.
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
With a stay at this vacation home in Marblehead, you'll be by the sea, within a 10-minute drive of Salem Witch Museum and Marblehead Museum & Historical ...
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
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!
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
This vacation home is in the heart of Salem, within a 5-minute walk of Salem Witch Trials Memorial and Salem Witch 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$738 per night from 7 Mar to 8 Mar
AU$738
includes taxes & fees
7 Mar - 8 Mar
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
"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
434 Holiday Homes
Lowest Price
AU$330
Highest Price
AU$738
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, Wonderful home sitting right between two terrific beaches!, 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, "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$417 per night from 26 Feb to 27 Feb
AU$417
includes taxes & fees
26 Feb - 27 Feb
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
Harborview Inn

Harborview Inn

3.5 out of 5
71 Western Avenue, Gloucester, MA
The price is AU$330 per night from 28 Feb to 1 Mar
AU$330
includes taxes & fees
28 Feb - 1 Mar
With a stay at Harborview Inn in Gloucester, you'll be near the beach, just a 4-minute walk from Fishermen's Memorial Monument and 5 minutes by foot from Pavilion ...
Harborview Inn
Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Gloucester
A stay at this cottage places you in the heart of Gloucester, within a 5-minute drive of Good Harbor Beach and Schooner Adventure.
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
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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
Don't see what you're looking for?
See all available properties in Gloucester
View all properties
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.