Title: Book the Best Chesapeake Bay WINERY Hotels in 2025 | Expedia.ca [Chesapeake Bay Travel Guide](https://expedia.ca/Chesapeake-Bay.dx6056980)[Hotels in Chesapeake Bay](https://expedia.ca/Chesapeake-Bay-Hotels.d6056980.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake Bay](https://expedia.ca/Chesapeake-Bay-Vacation-Rentals.d6056980.Travel-Guide-VacationRentals)[Flights to Chesapeake Bay](https://expedia.ca/Cheap-Flights-To-Chesapeake-Bay.d6056980.Travel-Guide-Flights)[Things to do in Chesapeake Bay](https://expedia.ca/Things-To-Do-In-Chesapeake-Bay.d6056980.Travel-Guide-Activities)[Chesapeake Bay Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake-Bay.d6056980.Car-Rental-Guide)[Chesapeake Bay Vacation Packages](https://expedia.ca/Chesapeake-Bay.d6056980.Destination-Travel-Guides) ![Virginia which includes a statue or sculpture, a high-rise building and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/33000/33013-Town-Point-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Chesapeake Bay ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chesapeake Bay Winery Hotels Tonight [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-03&endDate=2025-10-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6056980&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesapeake Bay Winery Hotels ![Business centre](https://images.trvl-media.com/lodging/2000000/1630000/1620700/1620663/76dd9569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/2000000/1630000/1620700/1620663/ad50dd42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1630000/1620700/1620663/934534ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 Bedroom | View from room](https://images.trvl-media.com/lodging/2000000/1630000/1620700/1620663/3bab73d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wedmore Place Williamsburg 9.6/10 Exceptional (1001) "Nice area and tavern" CA $188 CA $222 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Williamsburg-Hotels-Wedmore-Place.h1620663.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/106000000/105710000/105703000/105702932/8c36a65e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/106000000/105710000/105703000/105702932/59a55852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed](https://images.trvl-media.com/lodging/106000000/105710000/105703000/105702932/077c6e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/106000000/105710000/105703000/105702932/a7f6291c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Rose Gaming Resort Dumfries 9.6/10 Exceptional (326) "The hotel was great all the way around " CA $175 CA $203 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Dumfries-Hotels-The-Rose-Gaming-Resort.h105702932.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/61200/61186/d9298278.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/61200/61186/396fa824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/70000/61200/61186/64946b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/70000/61200/61186/f0f28a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Williamsbrg Busch Gardens Area by IHG Williamsburg 9.2/10 Wonderful (1162) "Very comfortable stay with even better customer service from a friendly staff." CA $103 CA $123 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Williamsburg-Hotels-Holiday-Inn-Express-Williamsbrg-Busch-Gardens-Area.h61186.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/79000000/78260000/78250300/78250218/b4a07692.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/79000000/78260000/78250300/78250218/cfceac55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/79000000/78260000/78250300/78250218/d3d20f28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, bed sheets](https://images.trvl-media.com/lodging/79000000/78260000/78250300/78250218/5ffd607a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Tappahannock Tappahannock 9.0/10 Wonderful (287) "Nice hotel! Super quiet all night, comfy bed" CA $158 CA $176 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Tappahannock-Hotels-Hampton-Inn-Tappahannock.h78250218.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111260000/111254600/111254598/95b6fb60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/112000000/111260000/111254600/111254598/f513b121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/112000000/111260000/111254600/111254598/f353fef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/112000000/111260000/111254600/111254598/de151289.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spark by Hilton Norfolk Norfolk 8.8/10 Excellent (217) "Staff were very friendly and rooms were very clean and new looking" CA $141 CA $166 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Norfolk-Hotels-Spark-BY-Hilton-Norfolk.h111254598.Hotel-Information) ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e422830e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/0c592b6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e8514eb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Direct Bay Front Double Queen Suite - Bayfront | View from room](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/e9bbde17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chincoteague Island Bayfront Resort Chincoteague 9.6/10 Exceptional (1002) "Very clean & right on the water! Would definitely stay again if in the area! " CA $159 CA $180 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Chincoteague-Hotels-Comfort-Suites-Chincoteague-Island-Bayfront-Resort.h295865.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/4000000/3110000/3105600/3105529/32e6f1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3110000/3105600/3105529/072954e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3110000/3105600/3105529/a9a662b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3110000/3105600/3105529/356a808d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Smithfield Station Smithfield 8.8/10 Excellent (472) "It was the perfect location… the room was immaculate and the service was amazing!" CA $216 CA $249 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Smithfield-Hotels-Smithfield-Station.h3105529.Hotel-Information) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/20000/13700/13601/eb9d2f7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/20000/13700/13601/afa29e47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Suite, 1 King Bed with Sofa bed, Non Smoking, Kitchenette (Efficiency)](https://images.trvl-media.com/lodging/1000000/20000/13700/13601/20ce9626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/13700/13601/aede8cc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Williamsburg Gateway Williamsburg 9.2/10 Wonderful (1186) "Great stay!" CA $126 CA $144 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Williamsburg-Hotels-Comfort-Inn-Williamsburg-Gateway.h13601.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (825) "Friendly staff, clean room, convenient location. " CA $160 CA $177 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/f0e8c5ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/5e121d6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/7b864253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/26700/26629/b9946eac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Triangle/Quantico Triangle 7.6/10 Good (1000) "The people were very friendly and accommodating. The rooms were nice. Warm in the hallways, but nice and cool in the rooms. " CA $105 CA $120 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Triangle-Hotels-Ramada-By-Wyndham-TriangleQuantico.h26629.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-17&endDate=2025-10-18®ionId=6056980&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Bay Hotel Reviews ![Hilton Vacation Club The Historic Powhatan Williamsburg](//images.trvl-media.com/lodging/1000000/870000/864100/864071/683f098a_y.jpg) ### Hilton Vacation Club The Historic Powhatan Williamsburg 10/10 Excellent "My second time and I love it " [](https://expedia.ca/Williamsburg-Hotels-The-Historic-Powhatan-Resort-By-Diamond-Resorts.h864071.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Tidewater Region](https://www.expedia.ca/1Star-Tidewater-Region-Hotels.s10-0-d553248635975748741.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Assateague Island National Seashore](https://www.expedia.ca/4Star-Assateague-Island-National-Seashore-Hotels.s40-0-d6075482.Travel-Guide-Filter-Hotels) - 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