Search Vacation Homes in Gloucester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 317 Vacation Homes in Gloucester with updated reviews, rates, and availability.

The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

10.0 out of 10, Exceptional, (42)
"Not only was Jill incredibly helpful and responsive, the house and surrounding area was beautiful. I stayed with my family - two adults and three kids - and there was more than enough room for everyone. The kitchen and bathrooms were well stocked, and a blender and snowcone maker really made it fun. Highly recommend!"
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer

Kings Creek

2.0 star property
2.0 out of 10, (1)
"We never got to stay at the property because Expedia never posted the booking and it is impossible to contact Expedia to resolve any type of issue. I wouldn't recommend that anyone use that site to book a reservation. We were traveling and was 3 hours from home and was turned away from the resort because Expedia had not given the information to the resort. We had to find last minute accommodation and are still trying tl get our money back. "
Kings Creek

Relaxing 1 bedroom 2019 Camper beside the Seven River

9.4 out of 10, Exceptional, (18)
" The location was great if you want a quiet place and close to the river. We enjoyed walking down to edge and watching the water. We also enjoyed walking around the neighborhood. The camper was very clean. Kimberly and her husband were very nice and helped with the few little problems that we had. We really enjoyed our stay there."
The price is AED 261
AED 638 total
includes taxes & fees
28 Jan - 29 January 2025
Relaxing 1 bedroom 2019 Camper beside the Seven River

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (89)
"We loved our stay. We were looking for somewhere away from the chaos of holiday in Williamsburg but accessible. It fit perfectly. House was quiet, clean and comfortable. Made for a wonderful weekend. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Sojourn Aviators Dream on Back River

9.6 out of 10, Exceptional, (14)
"We picked this location given friends live nearby, but it exceeded expectations. Beautiful view, incredible sunrise, and the kids loved the fireplace. Hadn't realized the kids bunk room doesn't have a door to close, but luckily noise wasn't a problem. "
The price is AED 481
AED 1,434 total
includes taxes & fees
30 Dec - 31 Dec
Sojourn Aviators Dream on Back River

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

10.0 out of 10, Exceptional, (14)
"The grounds of property are beautifully maintained and larger than expected. There was plenty of outdoor activities for the kids. We did not use the indoor pool, but did peak inside and it would have been perfect for a swim or pool party. We had breakfast at the Grill and the food was good with generous portions. The staff was very friendly and engaging. Our units were specious, clean and the beds were very comfortable. The ktchens were well appointed. The location was great as Colonial...
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.

Family friendly home near Colonial Williamsburg and Busch Gardens

9.8 out of 10, Exceptional, (33)
"Fabulous! Our 2nd visit and plan on staying again. Super Host"
Family friendly home near Colonial Williamsburg and Busch Gardens

Uncle Bill's Lodge & Soccer Pool Showdown

8.4 out of 10, Very Good, (7)
"Perfectly clean and comfortable but no privacy. Pet friendly but neighbor allowed their dog to come to fenced yard at all hours which made my 1 dog bark. Not sure if neighbor was owner. Great fenced yard but as I stated, no privacy. Homes close by even in backyard. Fine for families who want to visit from out of town visiting Busch Gardens/Water Country and CW as backyard is entertaining and home is affordable. Just not what we were looking for. Photos and description made us feel it would be...
Uncle Bill's Lodge & Soccer Pool Showdown

Top Rated Family Resort Destination. 4BDR lock-off from only $379

9.6 out of 10, Exceptional, (7)
"The home was very nicely furnished, very clean, and we enjoyed the 4 bedrooms and 4 bathrooms. The grounds were lively."
Top Rated Family Resort Destination. 4BDR lock-off from only $379

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

10.0 out of 10, Exceptional, (148)
"I knew when I found this listing that I may have uncovered a hidden gem and I was right! We stayed just for a long weekend but everything was cozy and the local towns were so friendly. We definitely enjoyed White Dog Bistro, Southwind Pizza and Richardsons. Even though we ate out most of our time, the house had most of the essentials if you chose to cook there. The hot tub and fire pit were favorites, we stopped at Food Lion just to get Marshmallows to roast. My husband caught lots of fish...
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

The Williamsburg Retreat - Gorgeous Private Acreage

10.0 out of 10, Exceptional, (128)
"This home is lovely, cozy and spacious. I loved all the thoughtful touches such as the home being decorated for Christmas as we were in Williamsburg for Christmas Town. Wow! Plenty of kids toys, books, play stations. Kitchen was well stocked even had a crockpot. Very clean. The porch is huge and enjoyed the scenery from the back porch while sipping coffee by the fire pit. A tray of delicious brownies awaited our arrival. Looking forward to a return stay"
The Williamsburg Retreat - Gorgeous Private Acreage

Large 4bed 2.5b home w/ fenced in back yard & deck

9.4 out of 10, Exceptional, (3)
"We stayed here for a wedding, there were seven adults and one toddler and one pup. It was great! Loved all the space, fenced in backyard for the pup and nice yard for kiddo games. Would definitely stay here again. "
The price is AED 1,131
AED 2,228 total
includes taxes & fees
26 Jan - 27 January 2025
Large 4bed 2.5b home w/ fenced in back yard & deck

Beachfront Urbanna Home w/ Gas Grill & Deck!

10.0 out of 10, Exceptional, (14)
"The house was amazing and we would stay there again!"
Beachfront Urbanna Home w/ Gas Grill & Deck!

Wyndham Kingsgate - 2 Bedroom Deluxe

9.2 out of 10, Wonderful, (13)
"The property was wonderful and very accommodating to people of all ages. The condo was accurately listed and had the basic amenities needed for a wonderful stay! "
Wyndham Kingsgate - 2 Bedroom Deluxe

Cozy Country setting with comforts of home

8.8 out of 10, Excellent, (15)
"Was very warm and inviting atmosphere. Easy to find and off the main traffic at the same time very convenient. "
Cozy Country setting with comforts of home

Colonial Brick Home Nestled in the Woods.

4.0 star property
9.8 out of 10, Exceptional, (25)
"This lovely home is in a quiet neighborhood and situated well between all the main area attractions. We visited Colonial Williamsburg, Busch Gardens, Jamestown, and Yorktown. All were simple to get to from the home. There is also a grocery and a lovely coffee shop, The 1607 Coffee Shop, both within a 5 minute drive. The beds were comfortable, and the home was actually more spacious than the pictures made it appear. It also has a workspace with a lovely view of the wooded backyard. We even heard...
Colonial Brick Home Nestled in the Woods.

Fun and Open Space Near Everything - Pool table, Hot Tub in Williamsburg

2.0 star property
9.6 out of 10, Exceptional, (4)
"Conveniently located for visiting Colonia Williamsburg, Jamestown, and Yorktown. The only negative comment I have is that there was a slight dog odor. I always rent pet-free properties because I am sensitive to the smell. Other than that we were pleased with the rental."
Fun and Open Space Near Everything - Pool table, Hot Tub in Williamsburg

Beautiful and Spacious 4 Bedroom, 4 Bath Estate in Williamsburg, VA

2.0 out of 10, (1)
Beautiful and Spacious 4 Bedroom, 4 Bath Estate in Williamsburg, VA

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

10.0 out of 10, Exceptional, (24)
"Great property. Wonderful views. Quiet and peaceful. Hosts were tremendous with their instructions and details regarding our stay."
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (40)
"We have stayed at Glenda’s place multiple times and love it every time. It’s the perfect place to reconnect with my family and enjoy the peace of the Rivah. Everything is clean and comfortable and well stocked. Thank you Glenda!"
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.
Don't see what you're looking for?
See all available properties in Gloucester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Gloucester

"Bee Haven" Cottage Retreat Near Colonial Williamsburg

10.0 out of 10, Exceptional, (89)
"We loved our stay. We were looking for somewhere away from the chaos of holiday in Williamsburg but accessible. It fit perfectly. House was quiet, clean and comfortable. Made for a wonderful weekend. "
"Bee Haven" Cottage Retreat Near Colonial Williamsburg

Welcome to this Waterfront Home with Amazing Views

10.0 out of 10, Exceptional, (19)
"Cozy!Clean!Great outdoor!"
The price is AED 551
AED 1,386 total
includes taxes & fees
1 Jan - 2 January 2025
Welcome to this Waterfront Home with Amazing Views

Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock

10.0 out of 10, Exceptional, (24)
"Great property. Wonderful views. Quiet and peaceful. Hosts were tremendous with their instructions and details regarding our stay."
Beautiful & Peaceful House Overlooking the River. Pets Welcome! Kayaks and Dock
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.