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 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-17&endDate=2025-10-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This 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) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6025644&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore Winery Hotels ![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) ![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) ![Daily breakfast for a fee](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/72680920.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 (1567) "Great property , large rooms and free breakfast!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Tiffany CA $118 CA $131 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.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) ![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) ![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) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (829) "The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie CA $143 CA $159 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.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) ![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) ![Reception](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/d6974a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/607bb91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Place Hotel Downtown Ocean City 9.2/10 Wonderful (1010) "Nice place, great staff." ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $61 CA $110 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Ocean-City-Hotels-Park-Place-Hotel.h13279522.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) ![Standard Single Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.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" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $266 CA $348 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/53a12ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/c89c29dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony, Oceanfront (Hearing Accessible)](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/0f74ca55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/4f3138fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Ocean City Oceanfront Downtown Ocean City 9.2/10 Wonderful (983) "Great hotel and service " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) dawn CA $135 CA $150 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.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) ![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) ![Staircase](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/7004874c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast Salisbury 10/10 Exceptional (159) "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!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $190 CA $212 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Standard Room, 2 Queen Beds, Oceanfront | Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/50868563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/9e9c92ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/52e157e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/4000000/3670000/3660800/3660765/298c40df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaLoft Oceanfront Hotel Midtown Ocean City 8.6/10 Excellent (367) "Great time with the family. Super walkable and beach front! " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathalie CA $111 CA $124 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Ocean-City-Hotels-Atlantic-OceanFront-Inn.h3660765.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/f42afa08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/7762f1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1008) "Great place to stay! " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole CA $101 CA $112 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/bd4d4a27.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 (940) "Room was clean and staff were friendly. They provided a nice breakfast with plenty of options. " ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy CA $144 CA $161 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, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/8bf1c888.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/w3633h2233x0y0-164d7bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/08a34731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/9b7ea9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Monte Carlo Ocean City Downtown Ocean City 7.8/10 Good (1013) "We stayed for the week and it was an excellent stay!" ![](https://a.travel-assets.com/egds/marks/flags/us.svg) Shamar CA $79 CA $115 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Ocean-City-Hotels-Hotel-Monte-Carlo-Ocean-City.h1866913.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=2025-10-31&endDate=2025-11-01®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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