Holiday Rentals in Gloucester

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Holiday Rentals in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (92)
"Excellent place to rest your head. Cozy, clean, and comfortable. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

10.0 out of 10, Exceptional, (145)
"’m almost hesitant to write this review because this place is just that good. My wife and I spent a perfect weekend here and couldn’t have asked for more. The house is beautifully appointed and thoughtfully decorated, creating an inviting and comfortable atmosphere from the moment you walk in.The entire upper floor is dedicated to the master suite, offering a third-story view that feels like a private retreat. The bed is one of the most comfortable we’ve ever slept in—like sinking into a cloud....
Relax, Refresh, Renew..Waterfront Cottage..Near Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (21)
"Lovely stop over on our way to family. Beautiful home decorated for the holidays and had all the amenities we needed plus little snacks! We got to the a beautiful sunset off the dock and our twins got their own rooms and bathroom. It would’ve cost more to get two rooms at Williamsburg hotel. So happy we got to stay here! Would love to stay the week during summertime! Beautiful home and location! "
Welcome to this Waterfront Home with Amazing Views

Radiant Gloucester House w/ Private Porch!

9.6 out of 10, Exceptional, (21)
"Home was perfect for our needs clean well decorated and close to plenty of downtown restaurants and area attractions "
Radiant Gloucester House w/ Private Porch!

Historic Cottage on Ware River Estate

10.0 out of 10, Exceptional, (259)
"Everything was so charming and cozy! We appreciated the little holidy touches for our Christmas away from home. I would definitely come again when in the area!"
Historic Cottage on Ware River Estate

A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

9.8 out of 10, Exceptional, (147)
"Great location to visit Williamsburg and the other nearby historic sites. "
A Sandy White Beach Retreat ** NEAR WILLIAMSBURG**

Kings Creek Plantation by Spinnaker

4.0 star property
9.0 out of 10, Wonderful, (41)
"Was convenient to everything in the Williamsburg area"
Kings Creek Plantation by Spinnaker

Private 5-acre Waterfront Peninsula with Beach

9.2 out of 10, Wonderful, (37)
"We had such a wonderful time! The location was absolutely beautiful and so peaceful. The house was very comfortable and clean making it easy to just relax. Note to future renters - the property and it's amenities have been greatly loved. The peddle boat rudder wasn't working, one of the kayaks was cracked and leaking, hot tub never got up to temperature, several nails were popping up out of the deck which had several loose boards and splinters, and the kitchen needed some work as the knobs were...
The price is €783
includes taxes & fees
20 Feb - 21 Feb
Private 5-acre Waterfront Peninsula with Beach

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

8.2 out of 10, Very good, (25)
"The house fit our need of 1 story, 2 bedrooms, and 2 baths. Some items have needed to be repaired for months ( based on previous reviews). House was clean. At check in, there was such a strong odor of whatever cleaner was used. After 30 minutes, l had a headache. The odor was gone the next morning. I would stay there sgain."
Super close to beaches, the historic triangle, and bush gardens!

Cottage on a Private Island in the York River

10.0 out of 10, Exceptional, (325)
"The house and location were perfect. We had plenty of space for two families to spread out, SO many kitchen items, lovely decorations, gorgeous views- this was the total package!!"
Cottage on a Private Island in the York River

Private 1300 sq ft Cottage in Historic Yorktown-w/ trolley access

10.0 out of 10, Exceptional, (137)
"This cottage is beautifully decorated, clean and in a quiet neighborhood within convenient walking distance from the historic district and the York River. "
Private 1300 sq ft Cottage in Historic Yorktown-w/ trolley access

Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

10.0 out of 10, Exceptional, (114)
"Very clean, exactly as described, would stay again!"
Heart of Williamsburg Guest House 3 Bedrooms, 2 Full Baths, Sleeps 6

Stunning! River-Front Log Cabin Near Williamsburg

10.0 out of 10, Exceptional, (41)
"Overall, this cabin was a great find! I didn’t want the children traveling too far from home, so this location was perfect! Only 90 minutes from our neighborhood. The communication with the host was punctual every time.No regrets!I'm looking forward to seeing more guest enjoy this cabin!Thanks again!"
Stunning! River-Front Log Cabin Near Williamsburg

Anvil Campground

2.5 star property
8.2 out of 10, Very good, (35)
"We stayed this past week with our two dogs, and it was a wonderful family vacation. We stayed in the Blacksmith Cottage, which was fully-furnished with everything we needed. The kitchen was clean and well-stocked with pots and pans, and the oven and fridge were great to have. The bathroom was clean and comfortable. The grounds were quiet and seemed very safe - we did hear the trains a few times, but with a white-noise speaker and some soft earplugs, it didn't bother us or the dogs at all. If...
The price is €87
includes taxes & fees
18 Feb - 19 Feb
Anvil Campground

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

9.8 out of 10, Exceptional, (16)
"Spacious."
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.

Wyndham Kingsgate - 2 Bedroom Deluxe

10.0 out of 10, Exceptional, (19)
"A lovely property and staff…highly recommend!"
Wyndham Kingsgate - 2 Bedroom Deluxe

Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

10.0 out of 10, Exceptional, (131)
"This was an extremely clean and enjoyable place to stay. It had very modern amenities along with sufficient cookware and kitchen necessities. It was a quiet and comfortable place to relax and unwind. It instantly has become one of my favorite places to visit.J. Hunt "
Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!

Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

9.4 out of 10, Exceptional, (117)
"Excellent place to enjoy 4 generations of my family. Plenty of space to play with my grandkids outside and games to enjoy on the inside. Very quiet neighborhood and plenty of privacy."
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.

3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill

10.0 out of 10, Exceptional, (186)
"We loved our stay at Fred’s condo! Perfect location with a great view. Absolutely wonderful!"
3 Bedroom, 3 Bath Condo on the James River in gated Kingsmill

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (41)
"Clean and clutter-free property right on the water! Loved it."
Cozy cottage on the Chesapeake Bay
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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Other types of properties in Gloucester you may be interested in

Holiday Inn Express Gloucester by IHG

3.5 star property
7.2 out of 10, Good, (574)
"Only issue was no one bothered to service our room until day 4 out of five. At that point we were resting and said no thanks even though it needed servicing. Breakfast was delicious every morning and very well stocked. "
The price is €93
includes taxes & fees
20 Feb - 21 Feb
Holiday Inn Express Gloucester by IHG

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (92)
"Excellent place to rest your head. Cozy, clean, and comfortable. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (21)
"Lovely stop over on our way to family. Beautiful home decorated for the holidays and had all the amenities we needed plus little snacks! We got to the a beautiful sunset off the dock and our twins got their own rooms and bathroom. It would’ve cost more to get two rooms at Williamsburg hotel. So happy we got to stay here! Would love to stay the week during summertime! Beautiful home and location! "
Welcome to this Waterfront Home with Amazing Views
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.

Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, we offer holiday rentals where you'll be only 13.8 mi (22.2 km) from Busch Gardens Williamsburg, offering you a more remote option if you want a quiet place to stay. Gloucester is known for its festivals and art.

What are some of the best holiday rentals that Gloucester has to offer?

Welcome to this Waterfront Home with Amazing Views : This highly rated holiday home rental in Gloucester is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books. Another good choice for your trip to Gloucester is "Bee Haven" Cottage Retreat Near Colonial Williamsburg.

How many holiday rentals are there in Gloucester?

Expedia has 20 holiday rentals for your stay in Gloucester.

What’s there to see and do in Gloucester?

Middle Peninsula State Park and Brown Park are a couple of scenic spots to enjoy the outdoors, whereas Gloucester Museum of History is one of the cultural attractions. Other places in town to visit include Rosewell Ruins and Main Street Center.

What’s a holiday rental in Gloucester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Gloucester. Holiday rentals feature amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for small groups.