Book Holiday Homes in Gloucester

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Gloucester

Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.

Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.

Yorktown
The price is AU$354 per night from 17 Aug to 18 Aug
AU$354
17 Aug - 18 Aug
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Yorktown, within a 15-minute drive of Fort Eustis and Colonial National Historical Park.
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.
Retreat to Fairytale Cottage with Pool, Kayak

Retreat to Fairytale Cottage with Pool, Kayak

Irvington
When you stay at this vacation home in Irvington, you'll be on a river, within a 5-minute drive of Historic Christ Church and Compass Entertainment Complex.
Retreat to Fairytale Cottage with Pool, Kayak
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

Lanexa
The price is AU$1,205 per night from 5 Aug to 6 Aug
AU$1,205
5 Aug - 6 Aug
includes taxes & fees
Located in Lanexa, this vacation home is within a 15-minute drive of Stonehouse Golf Club and Little Creek Reservoir Recreation Area.
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Save an average of 15% on thousands of hotels when you're signed in
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!
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
Pet-Friendly Gem w/ Private Dock in Deltaville!

Pet-Friendly Gem w/ Private Dock in Deltaville!

Deltaville
Located in Deltaville, this vacation home is on the waterfront, within a 10-minute drive of Deltaville Maritime Museum and Holly Point Nature Park.
Pet-Friendly Gem w/ Private Dock in Deltaville!
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
Kings Creek Plantation by TripForth

Kings Creek Plantation by TripForth

3.5 out of 5
191 Cottage Cove Lane, Williamsburg, VA
When you stay at this vacation home in Williamsburg, you'll be near the airport, a 4-minute drive from Water Country USA and 8 minutes from College of William ...
Kings Creek Plantation by TripForth
'Pop Castle' Historic Gem on the Rappahannock River

'Pop Castle' Historic Gem on the Rappahannock River

White Stone
Located in White Stone, this vacation home is on the waterfront, within a 10-minute drive of White Stone Beach and Steamboat Era Museum.
'Pop Castle' Historic Gem on the Rappahannock River
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.

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
397 Holiday Homes
Lowest Price
AU$152
Highest Price
AU$1,205
Popular accommodation
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental., Retreat to Fairytale Cottage with Pool, Kayak, 4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now, Private Beach & Deck: Bayfront Home in Hayes!, The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer, Pet-Friendly Gem w/ Private Dock in Deltaville!, Kings Creek, Kings Creek Plantation by TripForth, 'Pop Castle' Historic Gem on the Rappahannock River

Top trending hotels in Gloucester

Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 17 Aug to 18 Aug
AU$172
17 Aug - 18 Aug
includes taxes & fees
With a stay at Hampton Inn Gloucester in Gloucester, you'll be a 5-minute walk from Shoppes at Gloucester and 9 minutes by foot from Gloucester Youth ...
Hampton Inn Gloucester
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$191 per night from 12 Aug to 13 Aug
AU$191
12 Aug - 13 Aug
includes taxes & fees
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
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$233 per night from 20 Aug to 21 Aug
AU$233
20 Aug - 21 Aug
includes taxes & fees
With a stay at Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel, you'll be centrally located in Williamsburg, a 3-minute walk from ...
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Save an average of 15% on thousands of hotels when you're signed in
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 3 Sept to 4 Sept
AU$152
3 Sept - 4 Sept
includes taxes & fees
With a stay at Vacation Village At Williamsburg, you'll be centrally located in Williamsburg, within a 5-minute drive of Williamsburg Premium Outlets and College ...
Vacation Village At Williamsburg
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.