Book Holiday Homes in Gloucester
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Featured Holiday Homes in Gloucester

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

Perfect large river retreat -views, bunkroom, firepit, playset -by Williamsburg!

The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

Family fun Grotto waterfall Bethel Oasis

Charming 2-bedroom house on the Chesapeake Bay

Relax Water View Bike Walk 2 Town and Tides Inn

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
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 | 375 Holiday Homes |
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Lowest Price | AU$128 |
Highest Price | AU$149 |
Popular accommodation | A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**, Perfect large river retreat -views, bunkroom, firepit, playset -by Williamsburg!, The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer, Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!, Family fun Grotto waterfall Bethel Oasis, Charming 2-bedroom house on the Chesapeake Bay, Relax Water View Bike Walk 2 Town and Tides Inn, Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!, 4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now |
Top trending hotels in Gloucester

Hilton Vacation Club The Historic Powhatan Williamsburg

Vacation Village At Williamsburg

Wyndham Garden Williamsburg Busch Gardens Area

Comfort Inn Newport News - Hampton I-64
More ways to explore Gloucester
Top picks
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^Subject to availability and chosen travel dates.