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

"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
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 |
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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

Ocean House Hotel at Bass Rocks


Atlantis Oceanfront Inn
More ways to explore Gloucester
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^Subject to availability and chosen travel dates.