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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Gloucester Vacation Homes

Our top choices for Gloucester vacation homes

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

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
Exterior

Charming 2-bedroom house on the Chesapeake Bay

9.4 out of 10, Exceptional, (10)
"Property was very nice and has a lot history with it. "
Charming 2-bedroom house on the Chesapeake Bay
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Fridge, microwave, oven, stovetop

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!"
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Boat Dock & Kayaks: Waterfront Home in Deltaville!
Fridge, microwave, stovetop, dishwasher

Boat Dock & Kayaks: Waterfront Home in Deltaville!

10.0 out of 10, Exceptional, (1)
"Great place to stay for the weekend. Place was quiet and peaceful. The house furnished well with great amenities. Fishing and kayaking from off the dock. Also life jackets available for the kids for safety as well. Catching crabs off the docks, fishing, kayaking, paddle boarding. The house has nice deck in the back where we enjoyed morning coffee and afternoon and evening activities playing corn hole, and spent good time sitting in front of fire pit was great. It was pleasure to stay spent...
Boat Dock & Kayaks: Waterfront Home in Deltaville!
3BDR, 2BA townhome at The Historic Powhatan Resort, Sleeps 8
Outdoor dining

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

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"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!
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
Exterior detail

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

9.8 out of 10, Exceptional, (24)
"Great location for our wknd trip with the family to Busch Gardens.The rooms were clean and comfortable with everything we needed! The kids loved the pool in the evening. "
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
Pleasurable Escape Hampton
Fridge, microwave, oven, stovetop

Pleasurable Escape Hampton

9.4 out of 10, Exceptional, (18)
"The place was nice and met the needs of us. Even a late checkout which is greatly appreciated, However taking the bedding off should be apart of the cleaning fee. "
Pleasurable Escape Hampton
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
Fridge, microwave, oven, stovetop

Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground

10.0 out of 10, Exceptional, (15)
"The house was clean and beautifully laid out to meet the needs of our group. Any issues were very, very minor and taken care of swiftly. We would definitely consider renting it out again. "
The price is CA $586
CA $899 total
includes taxes & fees
Aug 25 - Aug 26
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Smart TV, books

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

10.0 out of 10, Exceptional, (62)
"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
Family fun Grotto waterfall Bethel Oasis
Fridge, microwave, oven, stovetop

Family fun Grotto waterfall Bethel Oasis

9.8 out of 10, Exceptional, (33)
"The property is as described. Cute and clean, we enjoyed our stay. Most importantly, the beds were comfortable which is a big deal when they are not. Would recommend this place for families. "
The price is CA $701
CA $1,018 total
includes taxes & fees
Aug 25 - Aug 26
Family fun Grotto waterfall Bethel Oasis
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Dining

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 $243
CA $426 total
includes taxes & fees
Sep 21 - Sep 22
Charming and spacious 4-bedroom farm retreat with horses - Relax and Unwind!
Family friendly home near Colonial Williamsburg and Busch Gardens
Exterior

Family friendly home near Colonial Williamsburg and Busch Gardens

9.8 out of 10, Exceptional, (41)
"We used this property for our family to attend a wedding. Everything about this property was perfect. The hosts have really anticipated all of our needs and I really couldn’t suggest anything more. It made our visit easy and relaxing. "
Family friendly home near Colonial Williamsburg and Busch Gardens
Chickahominy Riverside Guest Home 30 Minutes to Williamsburg!
Property grounds

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!
Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
Interior

Ivy's Cottage w/ Outdoor Movies Williamsburg Stay

10.0 out of 10, Exceptional, (35)
"Very nice place to stay. Clean and comfortable. "
Ivy's Cottage w/ Outdoor Movies Williamsburg Stay
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Sun loungers, beach towels

Charming 2-bedroom house with AC, WiFi in Mathews County Virginia

10.0 out of 10, Exceptional, (6)
"Beautiful views of the water 360 degrees around. Turtles can be found right in the driveway, along with a tiniest crabs you'll ever see. Perfect for kayaking and paddleboarding, which both are provided. The inside is extremely comfortable in every place you sit. The hot tub was the icing on the cake! Wish we'd stayed longer."
Charming 2-bedroom house with AC, WiFi in Mathews County Virginia
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Fridge, microwave, oven, stovetop

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

10.0 out of 10, Exceptional, (189)
"Every Mother’s Day our extended family leaves town to explore a new part of Virginia for the weekend. Our stay in Bohannon could change all that. We want to go back! This is a lovely and spacious home with a million thoughtful touches. The property itself is spectacular and our gang enjoyed the kayaks, paddle boat and fire pit. We rate this as our top Mother’s Day getaway so far and we’ve been doing this for six years! Highly recommend! "
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
Spacious waterfront home with dock and sunset view
Outdoor dining

Spacious waterfront home with dock and sunset view

9.4 out of 10, Exceptional, (6)
"Overall, we found the home to be very accommodating with outstanding water views! Plenty of bedrooms!The following suggestions are given in the spirit of making the rental more guest friendly.Make available a book or sheet with house rules, passwords, and helpful hints for local restaurants and shoppingBathroom hooks to hang clothes and towelsTubs are slippery! Non slip mates should be addedAdd bath soap bars to go with liquid soap and shampoos Bedrooms should have full length mirrors as the...
Spacious waterfront home with dock and sunset view
Fun and Open Space Near Everything - Pool table, Hot Tub in Williamsburg
Terrace/patio

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

2.0 star property
9.6 out of 10, Exceptional, (11)
"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
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

Comfort Inn Williamsburg Gateway

Comfort Inn Williamsburg Gateway

10/10 Excellent
"Clean, nice spot with breakfast. There was only one person working in the hotel when we checked in so we had to wait quite a while before someone could check us in which was kind of inconvenient. But otherwise nice spot "
Chandra 1-night trip
Posted 3 hours ago
Comfort Inn Williamsburg Gateway