Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

Gloucester
With a stay at this vacation home in Gloucester, you'll be on the beach, and 7.9 mi (12.7 km) from Ware Parish Church and 8.9 mi (14.2 km) from Fairfield ...
Opens in a new windowA Sandy White Beach Retreat ** NEAR WILLIAMSBURG**
Perfect large river retreat -views, bunkroom, firepit, playset -by Williamsburg!

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

West Point
When you stay at this vacation home in West Point, you'll be on the waterfront and 12 minutes by car from Chelsea.
Opens in a new windowPerfect large river retreat -views, bunkroom, firepit, playset -by Williamsburg!
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 ...
Opens in a new windowThe Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
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Heart of Irvington w/Fireplace Walk to Tides Inn &  restaurants - Dog friendly!

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

Irvington
A stay at this vacation home places you in the heart of Irvington, within a 5-minute drive of Historic Christ Church and Compass Entertainment Complex.
Opens in a new windowHeart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Family fun Grotto waterfall Bethel Oasis

Family fun Grotto waterfall Bethel Oasis

Hampton
With a stay at this vacation home, you'll be centrally located in Hampton, within a 10-minute drive of Hampton Coliseum and Langley Air Force Base.
Opens in a new windowFamily fun Grotto waterfall Bethel Oasis
Charming 2-bedroom house on the Chesapeake Bay

Charming 2-bedroom house on the Chesapeake Bay

White Stone
With a stay at this vacation home in White Stone, you'll be on a river, and 7.3 mi (11.7 km) from White Stone Beach and 8.2 mi (13.2 km) from Golden Eagle Golf ...
Opens in a new windowCharming 2-bedroom house on the Chesapeake Bay
Relax Water View Bike Walk 2 Town and Tides Inn

Relax Water View Bike Walk 2 Town and Tides Inn

Irvington
Located in Irvington, this vacation home is on a river, within a 10-minute drive of Historic Christ Church and Compass Entertainment Complex.
Opens in a new windowRelax Water View Bike Walk 2 Town and Tides Inn
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

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

Gwynn's Island
When you stay at this vacation home in Gwynn, you'll be on the beach and within a 5-minute drive of Gwynn's Island Musuem.
Opens in a new windowPeaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

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

Lanexa
Located in Lanexa, this vacation home is within a 15-minute drive of Stonehouse Golf Club and Little Creek Reservoir Recreation Area.
Opens in a new window4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
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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
375 Holiday Homes
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

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$149 per night from 15 Oct to 16 Oct
AU$149
15 Oct - 16 Oct
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 ...
Opens in a new windowHilton 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
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 ...
Opens in a new windowVacation Village At Williamsburg
Wyndham Garden Williamsburg Busch Gardens Area

Wyndham Garden Williamsburg Busch Gardens Area

3 out of 5
201 Water Country Pkwy, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$128 per night from 22 Sept to 23 Sept
AU$128
22 Sept - 23 Sept
includes taxes & fees
Located in Williamsburg, Wyndham Garden Williamsburg Busch Gardens Area is in the historical district, a 3-minute drive from Water Country USA and 6 minutes ...
Opens in a new windowWyndham Garden Williamsburg Busch Gardens Area
Save an average of 15% on thousands of hotels when you're signed in
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
The price is AU$129 per night from 30 Sept to 1 Oct
AU$129
30 Sept - 1 Oct
includes taxes & fees
With a stay at Comfort Inn Newport News - Hampton I-64 in Newport News (Central Newport News), you'll be within a 15-minute drive of Christopher Newport University ...
Opens in a new windowComfort Inn Newport News - Hampton I-64
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.