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
Stay at this vacation home in Hampton. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Buckroe Beach and Park and ...
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
Book a stay at this beach vacation home in Hayes. Enjoy a beach locale, patios, and an in-room coffeemaker. Popular attractions Hog Island and Big Island are ...
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
Stay at this vacation home in Williamsburg. Enjoy a water park, a garden, and a pool table. Popular attractions Busch Gardens Williamsburg and 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
Stay at this vacation home in Hampton. Enjoy private pools, a pool table, and cable/satellite TV service. Popular attractions Buckroe Beach and Park and Grandview ...
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
Stay at this vacation home in Williamsburg. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jamestown Settlement and Williamsburg Premium ...
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Riverfront Virginia Home - Dock, Fire Pit & Kayaks

Weems
Book a stay at this family-friendly vacation home in Weems. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Steamboat Era ...
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
Stay at this vacation home in Mathews. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Bethel Beach and Bethel Beach Natural ...
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
Stay at this vacation home in Williamsburg. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Busch Gardens Williamsburg and Water Country ...
Kings Creek
The Cracker Jack House: A Military Salute & Arcade!

The Cracker Jack House: A Military Salute & Arcade!

Surry
Book a stay at this family-friendly vacation home in Surry. Enjoy free WiFi, a garden, and a pool table. Popular attractions Chippokes Plantation State Park ...
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
391 Holiday Homes
Lowest Price
NZ$186
Highest Price
NZ$293
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 NZ$224 per night from 6 Apr to 7 Apr
NZ$224
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3.5-star business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
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 NZ$186 per night from 8 Apr to 9 Apr
NZ$186
includes taxes & fees
8 Apr - 9 Apr
Stay at this 3.5-star golf resort in Williamsburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the restaurant in ...
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 NZ$249 per night from 2 Apr to 3 Apr
NZ$249
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3-star spa hotel in Williamsburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...
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 NZ$293 per night from 6 Apr to 7 Apr
NZ$293
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star golf hotel in Williamsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
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.