Winery Hotels & Resorts in Chesapeake Bay from AU$100

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Bay Winery Hotels

Best Chesapeake Bay Winery Hotels

Wedmore Place

3.5 star property
9.6 out of 10, Exceptional, (1010)
"Nice area and tavern"
The price is AU$247
includes taxes & fees
3 Sept - 4 Sept
Wedmore Place

Summer at the Rivah in Irvington! Come see for yourself!

10.0 out of 10, Exceptional, (297)
"What a wonderful place to enjoy a peaceful, beautiful Mother's Day weekend with my lovely bride. We took long walks, enjoyed the local scene and just spent lots of time enjoying the porches. The cottage supports all of this perfectly. We couldn't ask for more and can't wait until our next opportunity to stay at the Key Cottage!"
Summer at the Rivah in Irvington! Come see for yourself!

Bruadair Guest House - Exquisite Waterfront Beach House

3.0 star property
9.8 out of 10, Exceptional, (114)
"Perfect getaway for a couple who wants to relax and reconnect"
Bruadair Guest House - Exquisite Waterfront Beach House

Kingsmill Resort

4.0 star property
8.8 out of 10, Excellent, (1007)
"A very nice place family oriented to relax."
The price is AU$369
includes taxes & fees
2 Sept - 3 Sept
Kingsmill Resort

Hilton Vacation Club Greensprings Williamsburg

3.0 star property
8.4 out of 10, Very good, (1013)
"Great place to stay at."
The price is AU$219
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Greensprings Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 star property
9.0 out of 10, Wonderful, (3000)
"Loved staying here !"
The price is AU$170
includes taxes & fees
5 Sept - 6 Sept
Hilton Vacation Club The Historic Powhatan Williamsburg

Bay Chalet

2.5 star property
Bay Chalet

The Tides Inn

4.0 star property
8.8 out of 10, Excellent, (157)
"A lovely stay"
The price is AU$888
includes taxes & fees
10 Sept - 11 Sept
The Tides Inn

Best Western Kilmarnock Hotel

2.5 star property
7.8 out of 10, Good, (687)
"Good stay for the price."
The price is AU$232
includes taxes & fees
21 Sept - 22 Sept
Best Western Kilmarnock Hotel

Whispering Pines by Hotel O Whitestone VA

2.5 star property
6.4 out of 10, (139)
"Property was clean and great for a one night stand before catching the Ferry to Tangier"
The price is AU$149
includes taxes & fees
2 Sept - 3 Sept
Whispering Pines by Hotel O Whitestone VA
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.

Top Chesapeake Bay Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia