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)[Things to do in Eastern Shore](https://expedia.co.uk/Things-To-Do-In-Eastern-Shore.d6025644.Travel-Guide-Activities)[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) # Search Winery Hotels in Eastern Shore - ![](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 [7 Dec - 8 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-12-07&endDate=2025-12-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [8 Dec - 9 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-12-08&endDate=2025-12-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6025644&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastern Shore Winery Hotels ![Indoor pool, seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/w3837h2557x3y4-d297081d.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/8cb72b67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Ocean City / Oceanfront Downtown Ocean City 9.0/10 Wonderful (1593) "Room was very clean, staff were the best.would definitely recommend staying there." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary £67 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/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) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.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) ![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 (858) "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Santa £86 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/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) ![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) ![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) ![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 (128) "The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael £133 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Sun deck](https://images.trvl-media.com/lodging/14000000/13280000/13279600/13279522/08f08113.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) ![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 (1051) "Yes very nice and great time " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £53 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Ocean-City-Hotels-Park-Place-Hotel.h13279522.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/4f3138fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/c89c29dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2475100/2475053/53a12ce9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Ocean City Oceanfront Downtown Ocean City 9.2/10 Wonderful (1002) "Amazing hotel and staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorielen £69 includes taxes & fees 14 Dec - 15 Dec [](https://www.expedia.co.uk/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) ![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) ![Room (Pineapple) | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/43000000/42380000/42378900/42378873/38798564.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 (165) "They have made my stay feel like I am family " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia [](https://www.expedia.co.uk/Salisbury-Hotels-Gillis-Grier-Bed-And-Breakfast.h42378873.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/3ee1ed2e.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1540000/1535900/1535860/9cdfab37.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/d959fb17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wingate by Wyndham North East North East 8.0/10 Very good (949) "Room was clean and staff were friendly. They provided a nice breakfast with plenty of options. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy £98 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/5700/5604/7762f1e3.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 | 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) ### Comfort Inn Gold Coast North Ocean City 8.2/10 Very good (1001) "Our stay was amazing. The rom was spacious and clean. The lobby was decorated so cute for the holidays makkng it very welcoming. Staff was so kind and helpful. Pool was clean and eat to access." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy £56 includes taxes & fees 10 Dec - 11 Dec [](https://www.expedia.co.uk/Ocean-City-Hotels-Comfort-Inn-Gold-Coast.h5604.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/12c14ee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/e198f6f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/3821fa37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/65000000/64660000/64657900/64657840/4bc17011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Main Street - Apartment C - Berlin, MD Downtown Berlin 9.4/10 Exceptional (28) "We loved everything about our stay! This place is adorable and the location is awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kelly K. £174 includes taxes & fees 16 Dec - 17 Dec [](https://www.expedia.co.uk/Ocean-City-Hotels-On-Main-Street-Apartment-Berlin.h64657840.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/4791e965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/c1ae5468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/acf287f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/83000000/82890000/82880900/82880842/a5883b4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quarry Landing - Center of Town & River View - 3 Bedroom Port Deposit 10/10 Exceptional (11) "Was a great stay would definitely stay again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jerel p. £178 includes taxes & fees 5 Jan - 6 Jan 2026 [](https://www.expedia.co.uk/Port-Deposit-Hotels-Cheerful-3-Bedroom-Cottage-In-The-Center-Of-Town-Located-On-High-Street.h82880842.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=2025-12-22&endDate=2025-12-23®ionId=6025644&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Eastern Shore Hotel Reviews ![Red Roof Inn Perryville](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/a62f5bd3_y.jpg) ### Red Roof Inn Perryville 10/10 Excellent "Clean " [](https://expedia.co.uk/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information) ## 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) - 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