Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Super close to beaches, the historic triangle, and bush gardens!

Super close to beaches, the historic triangle, and bush gardens!

Hampton
Located in Hampton (Fox Hill), this vacation home is within a 10-minute drive of Hampton University and Buckroe Beach and Park.
Super close to beaches, the historic triangle, and bush gardens!
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!
Colonial Brick Home Nestled in the Woods.

Colonial Brick Home Nestled in the Woods.

4 out of 5
Williamsburg
When you stay at this vacation home in Williamsburg, you'll be on a lake, a 5-minute drive from College of William and Mary and 8 minutes from Water Country ...
Colonial Brick Home Nestled in the Woods.
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Hampton Grandview Beach Waterfront with Indoor Pool

Hampton Grandview Beach Waterfront with Indoor Pool

Hampton
With a stay at this vacation home in Hampton (Fox Hill), you'll be within a 15-minute drive of Hampton University and Buckroe Beach and Park.
Hampton Grandview Beach Waterfront with Indoor Pool
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 10-minute drive of College of William and Mary and Jamestown Settlement.
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Weems
Located in Weems, this vacation home is within a 10-minute drive of Historic Christ Church and Compass Entertainment Complex.
Riverfront Virginia Home - Dock, Fire Pit & Kayaks
Small Town Getaway - close to in-town Mathews with a casual rural life

Small Town Getaway - close to in-town Mathews with a casual rural life

Mathews
A stay at this vacation home places you in the heart of Mathews, and within a 10-minute drive of Gwynn's Island Musuem.
Small Town Getaway - close to in-town Mathews with a casual rural life
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
The Cracker Jack House: A Military Salute & Arcade!

The Cracker Jack House: A Military Salute & Arcade!

Surry
Located in Surry, this vacation home is in a rural location, within a 15-minute drive of Chippokes Plantation State Park and Smith's Fort.
The Cracker Jack House: A Military Salute & Arcade!
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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
393 Holiday Homes
Lowest Price
AU$170
Highest Price
AU$268
Popular accommodation
Super close to beaches, the historic triangle, and bush gardens!, Private Beach & Deck: Bayfront Home in Hayes!, Colonial Brick Home Nestled in the Woods., Hampton Grandview Beach Waterfront with Indoor Pool, Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort., Riverfront Virginia Home - Dock, Fire Pit & Kayaks, Small Town Getaway - close to in-town Mathews with a casual rural life, Kings Creek, The Cracker Jack House: A Military Salute & Arcade!

Top trending hotels in Gloucester

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is AU$203 per night from 6 Apr to 7 Apr
AU$203
includes taxes & fees
6 Apr - 7 Apr
A stay at Holiday Inn Express Gloucester by IHG places you in the heart of Gloucester, a 4-minute drive from Gloucester Museum of History and 11 minutes from ...
Holiday Inn Express Gloucester by IHG
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$170 per night from 8 Apr to 9 Apr
AU$170
includes taxes & fees
8 Apr - 9 Apr
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
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$226 per night from 2 Apr to 3 Apr
AU$226
includes taxes & fees
2 Apr - 3 Apr
With a stay at Vacation Village At Williamsburg, you'll be centrally located in Williamsburg, a 4-minute drive from College of William and Mary and 13 minutes ...
Vacation Village At Williamsburg
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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$268 per night from 2 Apr to 3 Apr
AU$268
includes taxes & fees
2 Apr - 3 Apr
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
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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.