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.

A Cute and Cozy Cottage.
Have you made your summer vacay plans yet at the Rivah in Irvington?
10.0 out of 10, Exceptional, (265)
"Family gathering (two houses) to celebrate three sisters/mothers and participate in a fund-raising golf tournament for a local non-profit."
Have you made your summer vacay plans yet at the Rivah in Irvington?
Room
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
Pool
Wedmore Place
3.5 star property
9.4 out of 10, Exceptional, (985)
"Wonderful!"
The price is SAR 489
SAR 556 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Wedmore Place
Lobby sitting area
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 SAR 697
SAR 788 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Williamsburg Sampler B & B
Property grounds
Kingsmill Resort
4.0 star property
9.0 out of 10, Wonderful, (1002)
"It was a lovely place. My only complaint was that the walls are pretty thin and was really noisy with a family next door. We would like to visit again when the weather is warmer and we can enjoy more of the amenities. We particularly enjoyed the breakfast buffet and view of the James River. "
The price is SAR 634
SAR 901 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Kingsmill Resort
Sports facility
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2360)
"It was great"
The price is SAR 411
SAR 573 total
includes taxes & fees
30 Jum. I - 31 Jum. I
Hilton Vacation Club The Historic Powhatan Williamsburg
Exterior
The Tides Inn
4.0 star property
8.8 out of 10, Excellent, (139)
"I can’t wait to visit again when the renovations are completed."
The price is SAR 1,309
SAR 1,599 total
includes taxes & fees
27 Jum. I - 28 Jum. I
The Tides Inn
Outdoor pool
Greensprings Vacation Resort
3.0 star property
8.4 out of 10, Very Good, (1002)
"Friendly, amazing staff and overall very lovely stay!"
The price is SAR 371
SAR 528 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Greensprings Vacation Resort
Exterior
Best Western Kilmarnock Hotel
2.5 star property
8.0 out of 10, Very Good, (550)
"Wonderful front desk staff "
The price is SAR 484
SAR 548 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Best Western Kilmarnock Hotel
Exterior
Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
6.8 out of 10, (801)
"Was looking for clean comfortable room and bed and it passed"
The price is SAR 198
SAR 219 total
includes taxes & fees
4 Jum. II - 5 Jum. II
Super 8 by Wyndham Havre De Grace Aberdeen Area
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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.