Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

marblehead
Stay at this vacation home in Marblehead. Enjoy a fitness center, laundry facilities, and in-room jetted tubs. Popular attractions Salem Witch Museum and Salem ...
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean
"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 Good Harbor Beach and Wingaersheek Beach ...
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester
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, laundry facilities, and an in-room coffeemaker. Popular attractions Salem Witch Museum and New England ...
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
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Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Marblehead
Stay at this vacation home in Marblehead. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Salem Witch Museum and Marblehead Museum & Historical ...
Best location in Old Town home, 5 minutes to everything, enjoy the difference!
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wingaersheek Beach and Cape Ann are located ...
Beach Life Bliss - steps to the beach
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

Newbury
Stay at this vacation home in Newbury. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Seabrook Beach and Newbury Beach are located ...
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach

Hampton
Stay at this vacation home in Hampton. Enjoy a garden, laundry facilities, and patios. Popular attractions Hampton Beach and Seabrook Beach are located ...
Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach
Island SunRise: Sunsets too!  360 WaterViews! Waterfront, Grill, Firepit, Central AC

Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC

Newbury
Stay at this vacation home in Newbury. Enjoy a garden, laundry facilities, and patios. Popular attractions Seabrook Beach and Plum Island Point are located ...
Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC
House near down town Salem

House near down town Salem

Salem
Stay at this vacation home in Salem. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Salem Witch Museum and Witch ...
House near down town Salem
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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
575 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean, "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Best location in Old Town home, 5 minutes to everything, enjoy the difference!, Beach Life Bliss - steps to the beach, Walk to Beach. Private Nature and Bird Watching Trail. Quiet., Coastal marsh-view getaway with 2 decks, grill, AC & W/D - walk to beach, Island SunRise: Sunsets too! 360 WaterViews! Waterfront, Grill, Firepit, Central AC, House near down town Salem

Top trending hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Castle 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
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Ocean House Hotel at Bass Rocks
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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Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach motel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Atlantis Oceanfront 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.