Find Winery Hotels in Chesapeake Bay

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    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.

Terrace/patio
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
Business center
Wedmore Place
3.5 star property
9.4 out of 10, Exceptional, (992)
"We absolutely loved this hotel. The best part are the grounds and attached vineyard. It’s really beautiful we were so pleasantly surprised! "
The price is NT$4,210
per night
May 30 - May 31
Wedmore Place
Captain John Smith Suite | Premium bedding, individually decorated, individually furnished
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 NT$5,980
per night
May 29 - May 30
Williamsburg Sampler B & B
Couples treatment rooms, body treatments, aromatherapy
Kingsmill Resort
4.0 star property
9.0 out of 10, Wonderful, (1001)
"Overall my wife and I had a good stay. We stayed in building 20, apt. 1183. We could hear noise on the otherside of the door so thin walls. Room is a bit small. Plenty of towels in bathroom . Outdoor furniture would have been great to sit on to look at golf course or at night just to chill but light is very dim at night and chairs were metal, so they were kind of rusty and dirty. Would be great if complex would keep some cushions on inside of room to use for outdoor chairs."
The price is NT$5,437
per night
May 29 - May 30
Kingsmill Resort
Indoor pool, outdoor pool, pool umbrellas, sun loungers
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
8.8 out of 10, Excellent, (2360)
"Great stay, family reunion over Memorial Day weekend. Very clean, spacious rooms. Restaurant very accommodating. Five minutes to stores and fifteen to Colonial Williamsburg."
The price is NT$3,507
per night
May 30 - May 31
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 NT$12,836
per night
Jun 2 - Jun 3
The Tides Inn
Exterior
Greensprings Vacation Resort
3.0 star property
8.4 out of 10, Very Good, (1001)
"Friendly, amazing staff and overall very lovely stay!"
The price is NT$2,866
per night
May 29 - May 30
Greensprings Vacation Resort
Exterior
Best Western Kilmarnock Hotel
2.5 star property
8.0 out of 10, Very Good, (552)
"I did not like the condition of the ice machines on the first floor. Thet were outdated and dirty and nasty looking."
The price is NT$4,150
per night
Jun 2 - Jun 3
Best Western Kilmarnock Hotel
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, iron/ironing board
Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
6.8 out of 10, (802)
"Was looking for clean comfortable room and bed and it passed"
The price is NT$1,695
per night
Jun 3 - Jun 4
Super 8 by Wyndham Havre De Grace Aberdeen Area
Reception
Whispering Pines Motel
2.5 star property
6.2 out of 10, (123)
"Older motor lodge, rooms clean, staff friendly"
The price is NT$3,217
per night
May 29 - May 30
Whispering Pines Motel
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.

Chesapeake Bay Winery Hotels information

 

Winery Hotels in Chesapeake Bay

124

Highest price
NT$12,836
Cheapest price
NT$1,695
Number of guest reviews
7,260
Total number of hotels in Chesapeake Bay
14,160