Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Welcome to this Waterfront Home with Amazing Views

Welcome to this Waterfront Home with Amazing Views

Gloucester
The price is AU$609 per night from 30 Jan to 31 Jan
AU$609
includes taxes & fees
30 Jan - 31 Jan
Located in Gloucester, this vacation home is on the waterfront, within a 15-minute drive of Fairfield Foundation and Gloucester Public Library.
Welcome to this Waterfront Home with Amazing Views
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

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

Williamsburg
Located in Williamsburg, this vacation home is in a rural location, a 3-minute drive from Williamsburg National Golf Club and 5 minutes from Greensprings Greenway ...
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Kings Creek

Kings Creek

2 out of 5
191 Cottage Cove Ln, Williamsburg, VA
With a stay at Kings Creek in Williamsburg, you'll be a 4-minute drive from Water Country USA and 5 minutes from Busch Gardens Williamsburg.
Kings Creek
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Relaxing 1 bedroom 2019 Camper beside the Seven River

Relaxing 1 bedroom 2019 Camper beside the Seven River

Hayes
The price is AU$252 per night from 11 Feb to 12 Feb
AU$252
includes taxes & fees
11 Feb - 12 Feb
Located in Hayes, this vacation home is on a river, a 3-minute drive from Severn Yachting Center and 8 minutes from Woodville Park.
Relaxing 1 bedroom 2019 Camper beside the Seven River
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.

Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.

Williamsburg
With a stay at this vacation home in Williamsburg, you'll be within a 15-minute drive of Busch Gardens Williamsburg and College of William and Mary.
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
4BD home with gameroom and pool, close to Langley & PTC!

4BD home with gameroom and pool, close to Langley & PTC!

Hampton
With a stay at this vacation home in Hampton, you'll be within a 5-minute drive of Boo Williams Sportplex and Langley Air Force Base.
4BD home with gameroom and pool, close to Langley & PTC!
Private Beach & Deck: Bayfront Home in Hayes!

Private Beach & Deck: Bayfront Home in Hayes!

Hayes
Located in Hayes, this vacation home is on the waterfront, within a 15-minute drive of Crown Pointe Marina and Gloucester County Public Library.
Private Beach & Deck: Bayfront Home in Hayes!
Cozy cottage on the Chesapeake Bay

Cozy cottage on the Chesapeake Bay

Hallieford
When you stay at this vacation home in Piankatank, you'll be on the waterfront and 14 minutes by car from Gwynn's Island Musuem.
Cozy cottage on the Chesapeake Bay
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

Newport News
With a stay at this vacation home in Newport News (North Newport News), you'll be within a 15-minute drive of Fort Eustis and Christopher Newport ...
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
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See all available properties in Gloucester
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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
323 Holiday Homes
Lowest Price
AU$155
Highest Price
AU$609
Popular accommodation
Welcome to this Waterfront Home with Amazing Views , The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer, Kings Creek, Relaxing 1 bedroom 2019 Camper beside the Seven River, Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort., 4BD home with gameroom and pool, close to Langley & PTC!, Private Beach & Deck: Bayfront Home in Hayes!, Cozy cottage on the Chesapeake Bay, Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

Top trending hotels in Gloucester

Holiday Inn Express Gloucester, an IHG Hotel

Holiday Inn Express Gloucester, an IHG Hotel

3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is AU$155 per night from 10 Feb to 11 Feb
AU$155
includes taxes & fees
10 Feb - 11 Feb
A stay at Holiday Inn Express Gloucester, an IHG Hotel places you in the heart of Gloucester, a 3-minute drive from Gloucester Museum of History and 10 minutes ...
Holiday Inn Express Gloucester, an IHG Hotel
Welcome to this Waterfront Home with Amazing Views

Welcome to this Waterfront Home with Amazing Views

Gloucester
The price is AU$609 per night from 30 Jan to 31 Jan
AU$609
includes taxes & fees
30 Jan - 31 Jan
Located in Gloucester, this vacation home is on the waterfront, within a 15-minute drive of Fairfield Foundation and Gloucester Public Library.
Welcome to this Waterfront Home with Amazing Views
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Gloucester
Located in Gloucester, this vacation home is in a rural location, within a 15-minute drive of Fairfield Foundation and Gloucester Public Library.
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Save an average of 15% on thousands of hotels when you're signed in
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$204 per night from 3 Feb to 4 Feb
AU$204
includes taxes & fees
3 Feb - 4 Feb
Located in Williamsburg, Hilton Vacation Club The Historic Powhatan Williamsburg is in the historical district, a 4-minute drive from College of William and ...
Hilton Vacation Club The Historic Powhatan Williamsburg
Don't see what you're looking for?
See all available properties in Gloucester
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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.