Title: Book the Best Eastern Shore WINERY Hotels in 2025 | Expedia.ca [Eastern Shore Travel Guide](https://expedia.ca/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.ca/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Vacation Rentals in Eastern Shore](https://expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals)[Flights to Eastern Shore](https://expedia.ca/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Things to do in Eastern Shore](https://expedia.ca/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[Eastern Shore Car Rentals](https://expedia.ca/Car-Rentals-In-Eastern-Shore.d6025644.Car-Rental-Guide)[Eastern Shore Vacation Packages](https://expedia.ca/Eastern-Shore.d6025644.Destination-Travel-Guides) ![Choptank River Lighthouse](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/253000/253262-Eastern-Maryland.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Eastern Shore, MD ![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 Eastern Shore Winery Hotels Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore Winery Hotels ![Couples treatment rooms, body treatments, aromatherapy](https://images.trvl-media.com/lodging/16000000/15250000/15248500/15248443/e21481d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, body treatments, aromatherapy](https://images.trvl-media.com/lodging/16000000/15250000/15248500/15248443/5253d569.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room Selected at Check-in | Fireplace](https://images.trvl-media.com/lodging/16000000/15250000/15248500/15248443/a10b5b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/16000000/15250000/15248500/15248443/973b5288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Avenue Inn and Spa Downtown 9.6/10 Exceptional (1131) "Great facility " CA $112 CA $124 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Rehoboth-Beach-Hotels-The-Avenue-Inn-And-Spa.h15248443.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/0e7e3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/587ee69d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/14f2f155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/12e386c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Newark, DE Newark 9.6/10 Exceptional (4) "The staff was friendly and very accommodating. The rooms were clean and comfortable. We enjoyed the breakfast each morning. Our only complaint was there was no cold water coming out of the faucets in the room, only warm or hot water. We had to buy bottled water to drink." CA $177 CA $197 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Newark-Hotels-Residence-Inn-By-Marriott-Newark.h116852262.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/295900/295865/86f5de21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chincoteague Island Bayfront Resort Downtown 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) ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2557x3y4-d297081d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/8cb72b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2546x3y0-2a92d744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/01fa9013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City 9.0/10 Wonderful (1554) "The hotel and staff were great we will be back." CA $117 CA $130 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/08f08113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/d6974a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/fcecd38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/eb718924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Place Hotel Downtown Ocean City 9.2/10 Wonderful (1004) "Nice place, great staff." CA $65 CA $114 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.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) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (114) "Great INN super nice staff" CA $254 CA $334 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/37b6becc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/3c6abce0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Pineapple)](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/38798564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/a57ab64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast Salisbury 10/10 Exceptional (157) "An absolute gem of a stay. I will definitely be back! A perfect stop for an affordable and nice stay on your way to beach the next day!" CA $188 CA $211 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/w3836h2556x4y4-94fd2dfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/9fdb8323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/988e6cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/bc7d2f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Chesapeake Bay North Inn North East 8.0/10 Very good (934) "Helpful staff, clean rooms and very convenient to where I needed to be." CA $143 CA $160 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/North-East-Hotels-Best-Western-North-East-Inn.h1535860.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/a3a4bc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/f42afa08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/d3caf33c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking, Bay View](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/c80a3acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1001) "I liked that Denny's was right there and they honored a 10% discount with your stay at the hotel." CA $96 CA $107 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.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=2025-10-20&endDate=2025-10-21®ionId=6025644&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Shore Hotel Reviews ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [5 Star Hotels in St. Michaels](https://www.expedia.ca/5Star-St-Michaels-Hotels.s50-0-d5940.Travel-Guide-Filter-Hotels) - [Hotels near Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) - [Honeymoon Resorts and in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Apartments in Bellevue](https://www.expedia.ca/Bellevue-Apartments.d553248635975867527-aaApartments.Travel-Guide-Accommodation) - 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