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Check prices for these dates

Next weekend
14 Saf. - 16 Saf.
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Compare 324 Vacation Homes in Gloucester with updated reviews, rates, and availability.

Welcome to this Waterfront Home with Amazing Views
Living area

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

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

10.0 out of 10, Exceptional, (43)
"Met up with my adult kids and their partners for a few days together. Loved the location and the space. Loved that it is dog friendly. Home has everything you need, very well stocked and functional kitchen. Wish we had more time to spend there. Highly recommend this property."
The Greenhouse: A peaceful retreat minutes from all Williamsburg has to offer
Kings Creek
Indoor pool

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
Huge 4BDR/4BA townhouse (12) at Historic Powhatan Resort.
Fat Canary. Very popular high-energy bistro Great wines - 6.5 miles

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.
4BD home with gameroom and pool, close to Langley & PTC!
Game room

4BD home with gameroom and pool, close to Langley & PTC!

9.8 out of 10, Exceptional, (12)
"Alonzo was a great host! Communication was superb! The house is spacious and perfect for family entertainment. "
4BD home with gameroom and pool, close to Langley & PTC!
Private Beach & Deck: Bayfront Home in Hayes!
Hayes Vacation Rental | 3BR | 2BA | 2,100 Sq Ft | Stairs Required

Private Beach & Deck: Bayfront Home in Hayes!

10.0 out of 10, Exceptional, (16)
"Absolutely beautiful home right on the water! Living space was so spacious,enough seating for all of us ( 6 adults), bedrooms were comfortable. Outside was just a few steps from relaxing waterway. Sunrise/sunsets were beautiful. Highly recommend Niareaarea.area,lots lots of choices for d"
Private Beach & Deck: Bayfront Home in Hayes!
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Exterior

"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
Cozy cottage on the Chesapeake Bay
View from house

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

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

10.0 out of 10, Exceptional, (11)
"Enjoyed versus hotel nice to crash in the living room together instead of rooms. "
Newly built 5 Bedroom Rancher with 2 master's and a big yard with playground
The Williamsburg Retreat - Gorgeous Private Acreage
Magnificent private yard

The Williamsburg Retreat - Gorgeous Private Acreage

10.0 out of 10, Exceptional, (129)
"This house is simply amazing!!! Wonderful space for multiple families to gather, relax and cook family meals together. House was beautifully decorated for Christmas—a nice touch since we were three families far from home for the holiday. The house was exactly as pictured in the listing/photos and the owners were super easy to communicate with. House is minutes from Busch Gardens, Colonial Williamsburg, New Town and other attractions. The farm fresh eggs and brownies were a nice touch!"
The Williamsburg Retreat - Gorgeous Private Acreage
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Notice 4 kayaks on side of house for guests use!

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

10.0 out of 10, Exceptional, (149)
"My husband and I booked this property for a cozy winter weekend away. This is one of those properties that ends up being BETTER in person than the listing indicated. We didn't even leave the house the entire weekend. The kitchen was so well stocked that we just cooked our meals. The hot tub was so clean, relaxing and had he BEST view of the river. We were lucky enough for it to snow while were were there. It was a gorgeous scene! I really can't say enough good things about this property - they...
MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!
Large 4bed 2.5b home w/ fenced in back yard & deck
Living area

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

9.4 out of 10, Exceptional, (3)
"There were 6 of us, 4 adults and 2 children, 10 and under. Three bedrooms had queen sized beds and the 4th, 2 twin beds, which was perfect for the boys. The house was clean, well equipped...it was in need of an update...paint, some minor repairs...none of which affected our stay. The location was great for us, a safe and quiet neighborhood."
Large 4bed 2.5b home w/ fenced in back yard & deck
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Come stay in our Kilmarnock home. Just steps to downtown

Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>

9.8 out of 10, Exceptional, (127)
"Wonderful property, beautifully decorated and appointed with everything you could need for a stay in Kilmarnock. Warm and inviting, with a lovely mix of antiques and traditional comfortable furnishings. The owner is incredibly responsive and thoughtful. . "
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Beautiful and Spacious 4 Bedroom, 4 Bath Cottage in Williamsburg, VA
Exterior

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

2.0 out of 10, (1)
Beautiful and Spacious 4 Bedroom, 4 Bath Cottage in Williamsburg, VA
Beachfront Urbanna Home w/ Gas Grill & Deck!
Urbanna Vacation Rental | 3BR | 3.5BA | Stairs Required | 4,467 Sq Ft

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!
Beach House on Chesapeake Bay!
Private Beach on property

Beach House on Chesapeake Bay!

10.0 out of 10, Exceptional, (122)
"We spent an early Thanksgiving here at Mike's beautiful home. Probably one of the most well equipped vacation homes we have ever visited. The setting is incredibly beautiful, private yet close to shopping and restaurants. definitely will be coming back."
Beach House on Chesapeake Bay!
Cozy Country setting with comforts of home
Exterior

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
Top Rated Family Resort Destination. 4BDR lock-off from only $379
Carriage rides are popular but BOOK EARLY (same day) as reservations go fast!

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

9.6 out of 10, Exceptional, (8)
"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
The Martin House: Historic 1 Br Cottage
DSC 0026

The Martin House: Historic 1 Br Cottage

10.0 out of 10, Exceptional, (3)
"Loved all about it and will definitely go back. Street number is wrong on VRBO. Thankfully my sister lives in the area and was able to get us there."
The Martin House: Historic 1 Br Cottage
Berryville Shores : Deltaville Riverfront Getaway
Bright living room, high ceilings, incredible comfortable sectional and swivel chairs.

Berryville Shores : Deltaville Riverfront Getaway

2.0 star property
10.0 out of 10, Exceptional, (4)
"Came for a family Memorial for our Aunt Mary! It was a perfect place for us & so convenient to Our Aunts home & where the Memorial was held. Thank you!"
Berryville Shores : Deltaville Riverfront Getaway
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 property types in Gloucester

Welcome to this Waterfront Home with Amazing Views
Living area

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

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

10.0 out of 10, Exceptional, (144)
"’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
"Bee Haven" Cottage Retreat Near Colonial Williamsburg
Exterior

"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
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.