Find Winery Hotels in Chesapeake Bay

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

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 AED 482
AED 547 total
includes taxes & fees
27 May - 28 May
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 AED 683
AED 772 total
includes taxes & fees
27 May - 28 May
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 AED 621
AED 883 total
includes taxes & fees
27 May - 28 May
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 AED 403
AED 561 total
includes taxes & fees
30 May - 31 May
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 AED 1,282
AED 1,566 total
includes taxes & fees
27 May - 28 May
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 AED 364
AED 517 total
includes taxes & fees
30 May - 31 May
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 AED 474
AED 537 total
includes taxes & fees
27 May - 28 May
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 AED 194
AED 215 total
includes taxes & fees
4 Jun - 5 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area
Don't see what you're looking for?
See all available properties in Chesapeake Bay
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.