Title: TOP Winery Hotels in Eastern Shore, MD for 2026 | Expedia.co.uk [Eastern Shore Travel Guide](https://expedia.co.uk/Eastern-Shore.dx6025644)[Hotels in Eastern Shore](https://expedia.co.uk/Eastern-Shore-Hotels.d6025644.Travel-Guide-Hotels)[Holiday Rentals in Eastern Shore](https://expedia.co.uk/Eastern-Shore-Holiday-Rentals.d6025644.Travel-Guide-HolidayRentals)[Flights to Eastern Shore](https://expedia.co.uk/Cheap-Flights-To-Eastern-Shore.d6025644.Travel-Guide-Flights)[Eastern Shore Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Eastern-Shore.d6025644.Car-Hire-Guide)[Eastern Shore Holidays](https://expedia.co.uk/Eastern-Shore.d6025644.Holidays-City-Breaks) ![Long Wharf Park](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6286116/d4aad82a-b6ac-4cb6-992a-8f51658bb937.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [28 Jan - 29 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2026-01-28&endDate=2026-01-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Jan - 30 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [30 Jan - 1 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Feb - 8 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Eastern Shore hotels with winery ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.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 [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (870 reviews) "Polite and kind hotel manager" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard £83 includes taxes & fees 14 Feb - 15 Feb [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/9a672eb2.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) ![Lounge](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/19cea38d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking, Oceanfront 1st Floor | View from room](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/3f0d63a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Ocean City Oceanfront [](https://www.expedia.co.uk/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (1,001 reviews) "Room was clean and staff was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanette £68 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Ocean-City-Hotels-Courtyard-Ocean-City-Oceanfront.h2475053.Hotel-Information) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2556x3y3-8b958879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/a9dfd72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/793897ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/83b7c1f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront [](https://www.expedia.co.uk/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) Downtown Ocean City 9.0/10 Wonderful (1,580 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew £68 includes taxes & fees 4 Feb - 5 Feb [](https://www.expedia.co.uk/Ocean-City-Hotels-Hyatt-Place-Ocean-City-Oceanfront.h23511859.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.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) ![Standard Single Room, 1 King Bed | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.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) ### Kent Island Resort [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (132 reviews) "Beautiful hotel, nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim £128 includes taxes & fees 2 Feb - 3 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Suite, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/a0122816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/8836fadd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/8072f514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/f06ff3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham North East [](https://www.expedia.co.uk/North-East-Hotels-Best-Western-North-East-Inn.h1535860.Hotel-Information) North East 8.0/10 Very good (957 reviews) "Good stay. The room was clean, bed was super comfortable and the shower was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DeAnda £72 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/North-East-Hotels-Best-Western-North-East-Inn.h1535860.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/eb718924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/41a02ac9.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/14000000/13280000/13279600/13279522/9050a3a2.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/14000000/13280000/13279600/13279522/54e2685b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Place Hotel [](https://www.expedia.co.uk/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) Downtown Ocean City 9.2/10 Wonderful (1,090 reviews) "Always a good place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason £61 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/c81cf203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/215f0904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/62134013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/36374cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gillis Grier Bed & Breakfast [](https://www.expedia.co.uk/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) Salisbury 10/10 Exceptional (167 reviews) "Great hosts. Terrific breakfast. Very clean. Comfy bed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JoAnn [](https://www.expedia.co.uk/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/7762f1e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 | Blackout curtains, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/d3caf33c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking | View from room](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/806f9855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Gold Coast [](https://www.expedia.co.uk/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) North Ocean City 8.2/10 Very good (1,005 reviews) "Great staff and a great price very friendly, responsive hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James C £52 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3836h2556x4y4-1df22480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2556x3y4-92e5a8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/82de6f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24400/24345/w3837h2557x3y3-45d5f8dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Salisbury Plaza [](https://www.expedia.co.uk/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.Hotel-Information) Salisbury 6.4/10 (897 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence £65 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Salisbury-Hotels-Best-Western-Salisbury-Plaza.h24345.Hotel-Information) ![Indoor pool, seasonal outdoor pool, pool umbrellas, pool 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) ![Rooftop bar](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/5d8f1958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, Balcony, Partial Ocean View | Balcony view](https://images.trvl-media.com/lodging/2000000/1870000/1867000/1866913/07ae918d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Monte Carlo Ocean City [](https://www.expedia.co.uk/Ocean-City-Hotels-Hotel-Monte-Carlo-Ocean-City.h1866913.Hotel-Information) Downtown Ocean City 7.8/10 Good (1,000 reviews) "This is very nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rony £73 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2026-02-11&endDate=2026-02-12®ionId=6025644&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Shore Hotel Reviews ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [5 Star Hotels in Royal Oak ](https://www.expedia.co.uk/5Star-Royal-Oak-Hotels.s50-0-d6047042.Travel-Guide-Filter-Hotels) - [Algonquin Hotels ](https://www.expedia.co.uk/Algonquin-Hotels.d553248635975860123.Travel-Guide-Hotels) - [Bozman Hotels ](https://www.expedia.co.uk/Bozman-Hotels.d3000440434.Travel-Guide-Hotels) - [Beach Resorts & in Cambridge ](https://www.expedia.co.uk/Cambridge-Hotels-Beach-Hotels.0-0-d6608-tBeachHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Cambridge ](https://www.expedia.co.uk/Cambridge-Hotels-Budget-Hotels.0-0-d6608-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Casino Hotels in Cambridge ](https://www.expedia.co.uk/Cambridge-Hotels-Casino-Hotel.0-0-d6608-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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