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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Gloucester Vacation Homes

3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8
Relax in a classic outdoor seating area surrounded by a beautiful planter and brick facade.

3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8

10.0 out of 10, Exceptional, (5)
3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Stunning building with a central entrance, flanked by windows, set amidst beautifully manicured grounds.

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

9.6 out of 10, Exceptional, (164)
"We throughly enjoyed our time at the little blue house! We would definitely stay here again."
Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!
Charming 2-bedroom house on the Chesapeake Bay
Enjoy a peaceful retreat with a front porch seating area and fire pit, surrounded by trees.

Charming 2-bedroom house on the Chesapeake Bay

9.4 out of 10, Exceptional, (9)
"Property was very nice and has a lot history with it. "
Charming 2-bedroom house on the Chesapeake Bay
Retreat to Fairytale Cottage with Pool, Kayak
Steps lead up to a charming porch with arched windows and two comfortable rocking chairs.

Retreat to Fairytale Cottage with Pool, Kayak

10.0 out of 10, Exceptional, (11)
"It was fairytale cottage ! "
Retreat to Fairytale Cottage with Pool, Kayak
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!
Relax by the serene lake with a clear view, featuring a dock and Adirondack chairs.

Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!

2.0 star property
10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our weekend. The house was lovely and clean, and the lawn and dock were perfect for getting some sun and watching the ospreys tend their nest. Aaron greeted us and made us feel welcome and responded to the one or two questions we had during our stay. "
Charming 3-bedroom house in Deltaville with Stunning Views and Beautiful garden!
Fun and Open Space Near Everything - Pool table, Hot Tub in Williamsburg
Relax in the hot tub surrounded by a deck and serene views.

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

2.0 star property
9.6 out of 10, Exceptional, (10)
"Perfect location to all of the local attractions and super cozy accommodations! Would stay here 10 out of 10 times 😀"
Fun and Open Space Near Everything - Pool table, Hot Tub in Williamsburg
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Enjoy cooking in this well-lit kitchen with a central island and microwave.

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

10.0 out of 10, Exceptional, (2)
"Communication was great from the initial booking. Spacious, clean, and very private. Great accommodations and up to date appliances/furniture. Canoe is a lovely addition that we took pretty far down the river to explore. Would absolutely return and recommend to others!"
The price is CA $550
CA $1,061 total
includes taxes & fees
Aug 31 - Sep 1
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Kings Creek
Front of property

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
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Cozy living space with a fireplace, dining area, and home office setup.

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

10.0 out of 10, Exceptional, (60)
"We had a wonderful time and enjoyed the pool and convenient location. It was a pleasure meeting the owners of this beautiful property as well. Great vacation ! We would definitely come back here."
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Enjoy meals together at the central island and dining table, set for six.

Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!

10.0 out of 10, Exceptional, (11)
"Nice, clean place with thoughtful touches, plenty of space, and amazing grounds. The owner was kind enough to let the kids meet the new puppies. Definitely would stay again stay "
The price is CA $268
CA $458 total
includes taxes & fees
Sep 9 - Sep 10
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Steps away from Gloucester Marina & Restaurant
Stunning two-story house with a central entrance, flanked by windows and a garage door.

Steps away from Gloucester Marina & Restaurant

10.0 out of 10, Exceptional, (33)
"Great house. Very clean and well stocked. Will stay again!"
Steps away from Gloucester Marina & Restaurant
Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!
Relax on the lakeside deck, surrounded by lush greenery and serene waters.

Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!

9.6 out of 10, Exceptional, (32)
"Nice and quiet. Excellent choice if you are looking for an outdoor get away. "
Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!
Charming Waterfront Cottage Small Beach
Enjoy a romantic dinner for two on this deck overlooking the water.

Charming Waterfront Cottage Small Beach

10.0 out of 10, Exceptional, (9)
"The house was exactly as listed, with the bonus of sweet touches appreciated by the women in our group. Four of us fit comfortably, and we really enjoyed starting and ending our day in the sunroom, viewing the sky. Excellent communication with the host when we needed it. We would stay here again for sure!"
Charming Waterfront Cottage Small Beach
Huge water view 2/2 condo in "Kingsmill on the James"
Enjoy waterfront views of the marina and docked boats from the comfort of this serene setting.

Huge water view 2/2 condo in "Kingsmill on the James"

10.0 out of 10, Exceptional, (64)
"What a great place to stay roomy,super clean. Great location easy to rent and find. Nice place to stay close to lot of places. The owner decorated for Christmas what nice touch when you walk in"
Huge water view 2/2 condo in "Kingsmill on the James"
Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
Relax in a cozy seating area with a comfortable bench and wicker chair, surrounded by a large window and a potted plant.

Ivy's Cottage w/ Outdoor Movies Williamsburg Stay

10.0 out of 10, Exceptional, (34)
"Very nice place to stay. Clean and comfortable. "
Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
Kings Creek Plantation by TripForth
Relax on the deck surrounded by mature trees in a peaceful neighborhood setting.

Kings Creek Plantation by TripForth

3.5 star property
8.4 out of 10, Very good, (41)
"This was probably the best property that I've stayed at, maybe ever. I had a family of 8 and the two apartments that we shared were perfect. I will be staying here again"
Kings Creek Plantation by TripForth
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Enjoy cooking in this well-equipped kitchen with appliances and a ceiling fan.

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

9.4 out of 10, Exceptional, (124)
"Great location for a weekend spent at Jamestown, Colonial Williamsburg and Busch Gardens! Awesome that we got to use the canoe! Also, really nice kitchen!"
Quiet Riverfront House with Private Sandy Beach. Close to Colonial Williamsburg.
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.
Traditional two-story home with a central entrance and symmetrical facade, set amidst mature trees and well-manicured grounds.

Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.

9.6 out of 10, Exceptional, (38)
"Cozy, super quiet, comfortable"
The price is CA $248
CA $314 total
includes taxes & fees
Aug 17 - Aug 18
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.
Cozy cottage on the Chesapeake Bay
Sit on the dock and enjoy the serene lake view.

Cozy cottage on the Chesapeake Bay

9.8 out of 10, Exceptional, (46)
"Easy access to the property and to town. Very quite and comfy."
Cozy cottage on the Chesapeake Bay
Delightful 1 Bedroom RV Near Ft. Eustis
Smart TV, video games

Delightful 1 Bedroom RV Near Ft. Eustis

9.6 out of 10, Exceptional, (4)
"I can get a hold of the property manager easily and she responds back very quickly! I was actually surprised at how fast she did respond!It's a quite,safe neighborhood. Exactly what I was looking for! I'm only 10 minutes away from my current job, close to the beach and other new experiences. It's a great place!"
Delightful 1 Bedroom RV Near Ft. Eustis
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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Top Gloucester Hotel Reviews

Patriots Inn

Patriots Inn

10/10 Excellent
"There was nothing bad to say. The Employees are outstanding, patient and respectful. We will be back again. "
Veronica 3-night trip
Posted 6 hours ago
Patriots Inn