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.

Wedmore Place
Pool
Wedmore Place
3.5 star property
9.4 out of 10, Exceptional, (1006)
"Simply the very best experience we could ask for! Barbara and the staff were super sweet and the room was soooo nice! The entire atmosphere there is extremely beautiful. Stayed there all weekend for my girlfriend's birthday and it did NOT disappoint in any way. Loved visiting the winery on property and being so close to Jamestown island and all the amazingly beautiful and historic areas that surround the property. The feel was less hotels and more bed and breakfast but with the services you...
The price is AED 637
AED 746 total
includes taxes & fees
24 Nov - 25 Nov
Wedmore Place
It’s Autumn on the Northern Neck! Why does it seem so inviting?! Come find out!
A Cute and Cozy Cottage.
It’s Autumn on the Northern Neck! Why does it seem so inviting?! Come find out!
10.0 out of 10, Exceptional, (285)
"Great place to stay while in Irvington!"
It’s Autumn on the Northern Neck! Why does it seem so inviting?! Come find out!
Kingsmill Resort
Property grounds
Kingsmill Resort
4.0 star property
8.8 out of 10, Excellent, (1001)
"The shower seals were not good. This causes excess water to get in the floor which caused us to use our towels to mop the floor. We were in building 10 room 5191. Otherwise the stay was nice. "
The price is AED 534
AED 785 total
includes taxes & fees
25 Nov - 26 Nov
Kingsmill Resort
Hilton Vacation Club Greensprings Williamsburg
Exterior
Hilton Vacation Club Greensprings Williamsburg
3.0 star property
8.4 out of 10, Very Good, (1007)
"Room had some issues with cable tv not connected and stove not plugged in but overall nice place to stay!"
The price is AED 247
AED 387 total
includes taxes & fees
3 Dec - 4 Dec
Hilton Vacation Club Greensprings Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg
Pool
Hilton Vacation Club The Historic Powhatan Williamsburg
3.5 star property
9.0 out of 10, Wonderful, (2543)
"Luxurious condo. Very comfortable. "
The price is AED 209
AED 345 total
includes taxes & fees
3 Dec - 4 Dec
Hilton Vacation Club The Historic Powhatan Williamsburg
The Tides Inn
Aerial view
The Tides Inn
4.0 star property
8.8 out of 10, Excellent, (152)
"Gorgeous setting, friendly staff, beautifully decorated rooms, as spotless and comfortable. We’ll, absolutely be returning."
The price is AED 1,121
AED 1,390 total
includes taxes & fees
5 Dec - 6 Dec
The Tides Inn
Best Western Kilmarnock Hotel
Exterior
Best Western Kilmarnock Hotel
2.5 star property
7.8 out of 10, Good, (619)
" I never give reviews but the girl who chcked us in last night at 10:40 Pm was so sweet. Pleasant.and kind with my two small. Sleepy children. I was in a rush and dont remenber her name but she really left an impression on me and my children. I also loved having a pizza hut classic nearby. We do not have any in PA."
The price is AED 474
AED 537 total
includes taxes & fees
24 Nov - 25 Nov
Best Western Kilmarnock Hotel
Whispering Pines Motel
Room
Whispering Pines Motel
2.5 star property
6.4 out of 10, (137)
"Excellent location, super accommodating managing staff"
Whispering Pines Motel
Super 8 by Wyndham Havre De Grace Aberdeen Area
Exterior
Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
6.6 out of 10, (857)
"Had a lovely time"
The price is AED 181
AED 201 total
includes taxes & fees
10 Dec - 11 Dec
Super 8 by Wyndham Havre De Grace Aberdeen Area
Colonial Gardens
Room
Colonial Gardens
3.5 star property
9.8 out of 10, Exceptional, (91)
"Colonial Gardens B&B is a gem nestled close to the living museum of Colonial Williamsburg. Angela, the warm and welcoming owner/proprietor, goes above and beyond with her local knowledge, steering us to fantastic dining spots and must-see attractions. The B&B's decor perfectly captures the colonial charm, creating a cozy atmosphere that complements the area's rich history. The beds are heavenly - I've never slept so well away from home! We loved the spaciousness and cleanliness of the rooms. We...
Colonial Gardens
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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