Find Winery Hotels in Chesapeake Bay

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Pick from 124 Chesapeake Bay Winery Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Have you made your summer vacay plans yet at the Rivah in Irvington?
10.0 out of 10, Exceptional, (267)
"Very comfortable historic house with quality updates that do no damage to that ambiance. Well furnished and decorated. Quite sizeable interior with front and rear porches. Fully outfited with any utensils and appliances you'll need. Exceptionally groomed grounds with lush vegetation. Highly recommend."
Have you made your summer vacay plans yet at the Rivah in Irvington?
Colonial Gardens
3.5 star property
9.8 out of 10, Exceptional, (84)
"I had never stayed in a bed-and-breakfast before, but my wife convinced me it would be fun. Little did I know how great this experience would be. When we arrived, we were greeted by Angela, the innkeeper. What a wonderful woman. A great host, a great cook, and a wealth of information about Williamsburg. This may have been one of our greatest vacations we would gladly go back again. Angela, thank you again for a great time. Andy and Donna."
Colonial Gardens
A Williamsburg White House
3.5 star property
9.6 out of 10, Exceptional, (155)
"Breakfasts are unbelievably excellent."
The price is $199
$225 total
includes taxes & fees
Jun 9 - Jun 10
A Williamsburg White House
Wedmore Place
3.5 star property
9.4 out of 10, Exceptional, (1002)
"This is a nice boutique hotel, very quiet and peaceful. Parking is easy, there is an elevator and everything is easy to navigate. The bed was comfortable, pillows not so much. They need to be replaced. Bathroom had an awkward shower with only a hand held shower attachment but also a full tub. There was a fireplace but it wasn’t functional. Pool is small, not heated. The grounds are beautiful. "
The price is $139
$157 total
includes taxes & fees
Jun 10 - Jun 11
Wedmore Place
Williamsburg Sampler B & B
3.0 star property
9.4 out of 10, Exceptional, (302)
"Nice, charming, and delightful b&b. Had wonderful and comfortable stay. Breakfast was great. Laura was the perfect hostess, made us feel welcomed. Definitely staying here again when back in the area! "
The price is $197
$223 total
includes taxes & fees
Jun 6 - Jun 7
Williamsburg Sampler B & B
Cedars of Williamsburg Bed & Breakfast
3.0 star property
9.2 out of 10, Wonderful, (500)
"I would happily stay here again! Alex, the owner, served breakfast each day and chats with people. Leroy, the manager, is friendly, helpful, and welcoming. You couldn’t pick a better location in Williamsburg to be close to W&M or Colonial Williamsburg. Parking is behind the building and it was easy to get in and out. The area is quiet at night and very safe. I had high expectations when I booked my stay here and they were exceeded! Everything you’d expect and want from a B&B."
The price is $160
$181 total
includes taxes & fees
Jun 16 - Jun 17
Cedars of Williamsburg Bed & Breakfast
Williamsburg Manor B&B
3.0 star property
9.2 out of 10, Wonderful, (248)
"We loved our stay. The bed was so so comfortable. One of the most comfy beds we've slept in! The b&b is adorable, walking distance to everything, and the breakfast is homemade cooked fresh and absolutely delicious! Feels more like you are spending your vacation in a nice home with all the amenities rather than a hotel/inn since they keep it so quaint and homey! We will absolutely stay again when we come back to Williamsburg!! Thank you!"
The price is $180
$203 total
includes taxes & fees
Jun 11 - Jun 12
Williamsburg Manor B&B
Kingsmill Resort
4.0 star property
9.0 out of 10, Wonderful, (1002)
"Excellent place to unwind."
The price is $220
$298 total
includes taxes & fees
Jun 11 - Jun 12
Kingsmill Resort
Williamsburg Lodge, Autograph Collection
4.0 star property
9.0 out of 10, Wonderful, (1003)
"Love this property! Wonderful staff...everyone is so friendly. Food and bar are excellent. Didn't use other facilities, but everything we experienced was top notch and the best possible location."
The price is $195
$220 total
includes taxes & fees
Jun 24 - Jun 25
Williamsburg Lodge, Autograph Collection
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2381)
"Room was a nice two bedroom suite, we had booked a single bedroom suite but by arrival were upgraded. One room had a king size bed with private bathroom while the other room was a pair of twin beds with a bathroom off of the main room of the suite. There was a full, if small, kitchen, compact/stacked washer and dryer, dinner table with seating for 6, and a setting or living room area with a pair of chairs and a couch that was also a pull-out bed. Room was very spacious and included a wooden...
The price is $105
$147 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Vacation Club The Historic Powhatan Williamsburg
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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.

Chesapeake Bay Winery Hotels information

 

Winery Hotels in Chesapeake Bay

124

Highest price
$379
Cheapest price
$53
Number of guest reviews
7,332
Total number of hotels in Chesapeake Bay
14,138