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 NZ$786 per night from 23 Mar to 24 Mar
NZ$786
includes taxes & fees
23 Mar - 24 Mar
Stay at this vacation home in Salem. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Salem Maritime National Historic Site and New ...
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
The price is NZ$625 per night from 6 Mar to 7 Mar
NZ$625
includes taxes & fees
6 Mar - 7 Mar
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and patios. Popular attractions Wingaersheek Beach and Plum Cove Beach are located ...
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
Stay at this vacation home in Swampscott. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Salem Harbor and Salem ...
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
Stay at this vacation home in Marblehead. Enjoy free WiFi, balconies, and cable/satellite TV service. Popular attractions Marblehead Museum & Historical Society ...
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
Book a stay at this family-friendly vacation home in Gloucester. Enjoy free WiFi, a garden, and patios. Popular attractions Good Harbor Beach and Long 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
Stay at this vacation home in Salem. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions New England Pirate Museum and Salem Witch ...
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 NZ$833 per night from 4 Mar to 5 Mar
NZ$833
includes taxes & fees
4 Mar - 5 Mar
Stay at this vacation home in Newburyport. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Seabrook Beach and Plum Island Point are ...
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,
Stay at this vacation home in Gloucester. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Rocky Neck Art Colony and The Gorton Theatre ...
"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
Book a stay at this beach vacation home in Manchester-by-the-Sea. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions West Beach and ...
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
NZ$377
Highest Price
NZ$833
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
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
Beauport Hotel Gloucester
Harborview Inn

Harborview Inn

3.5 out of 5
71 Western Avenue, Gloucester, MA
The price is NZ$377 per night from 5 Mar to 6 Mar
NZ$377
includes taxes & fees
5 Mar - 6 Mar
Stay at this 3.5-star B&B in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Harborview Inn
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Vista
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Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
The price is NZ$625 per night from 6 Mar to 7 Mar
NZ$625
includes taxes & fees
6 Mar - 7 Mar
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and patios. Popular attractions Wingaersheek Beach and Plum Cove Beach are located ...
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.