Title: The 10 Best Hotels Near Tilmon's Island Winery, Sudlersville from CAย $109 | Expedia.ca [Vacation Rentals in Sudlersville](https://expedia.ca/Sudlersville-Vacation-Rentals.d6359188.Travel-Guide-VacationRentals)[Tilmon's Island Winery Car Rentals](https://expedia.ca/Car-Rentals-In-Tilmons-Island-Winery.d553248621532662416.Car-Rental-Guide)[Tilmon's Island Winery Vacations](https://expedia.ca/Tilmons-Island-Winery-Sudlersville.d553248621532662416.Vacation-Attraction) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Tilmon's Island Winery, Sudlersville from CA $109 - ![](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 prices for these dates Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Tilmon's Island Winery hotels ![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) ![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) ![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.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) 18.2 km from Tilmon's Island Winery 8.6/10 Excellent (861) "Everything was well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ahmed CA $138 CA $153 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.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/1000000/50000/40400/40352/8b9992bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) 18.1 km from Tilmon's Island Winery 7.2/10 Good (422) "Professional staff, warm greetings clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. Nicholas and Mrs. Karen CA $98 CA $109 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.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=2026-01-09&endDate=2026-01-10®ionId=553248621532662416&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Tilmon's Island Winery Hotel Reviews ![Fairfield Inn & Suites by Marriott Middletown](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/52c8cc19_y.jpg) ### Fairfield Inn & Suites by Marriott Middletown 10/10 Excellent "Clean room, great staff, recommended. " [](https://expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Holiday Inn Express Hotel & Suites Dover by IHG](https://images.trvl-media.com/lodging/1000000/600000/597800/597727/6d0ff772_y.jpg) ### Holiday Inn Express Hotel & Suites Dover by IHG 10/10 Excellent "We had a wonderful stay. Thanks " [](https://expedia.ca/Dover-Hotels-Holiday-Inn-Express-Hotel-Suites-Dover.h597727.Hotel-Information) ![Hampton Inn Dover](https://images.trvl-media.com/lodging/1000000/40000/34500/34429/8eb0188e_y.jpg) ### Hampton Inn Dover 10/10 Excellent "Great sleep ๐Ÿ‘๐Ÿ‘" [](https://expedia.ca/Dover-Hotels-Hampton-Inn-Dover.h34429.Hotel-Information) ![Hilton Garden Inn Dover](https://images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/eab21539_y.jpg) ### Hilton Garden Inn Dover 10/10 Excellent "The hotel was very clean, the staff extremely courteous, and the food was surprisingly good for a hotel. We love that itโ€™s pet friendly, and our dog and cat were welcomed with much fawning and many scritches. " [](https://expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![Bally's Dover Casino Resort](https://images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "Great hotel with friendly staff." [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/2000000/1790000/1781300/1781239/817be2e3_y.jpg) ### Quality Inn 10/10 Excellent "Very pleasant experience. " [](https://expedia.ca/Dover-Hotels-Quality-Inn.h1781239.Hotel-Information) ![Wyndham Garden Dover](https://images.trvl-media.com/lodging/1000000/530000/520100/520035/cf1236f9_y.jpg) ### Wyndham Garden Dover 10/10 Excellent "Always a restful stay." [](https://expedia.ca/Dover-Hotels-Wyndham-Garden-Dover.h520035.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Very nice" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Holiday Inn Express & Suites Middletown by IHG](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131_y.jpg) ### Holiday Inn Express & Suites Middletown by IHG 10/10 Excellent "Great rooms and awesome hospitality " [](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ## Hotels near other Tilmon's Island Winery attractions ### Pinkney Park Explore the great outdoors at Pinkney Park, a lovely green space in Millington. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=924440153884332032) ### Crumpton Auction Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662415) ### Crumpton Park After visiting Crumpton Park, make a plan to see the other sights and activities in Crumpton. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=924439696180879360) ### Chase Island Commune with nature and explore the great outdoors at Chase Island during your travels in Chestertown. Experience the area's festivals and art scene. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=924439142769758208) ### Church Hill Theatre You can enjoy a show at Church Hill Theatre during your trip to Church Hill. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=844528418122231808) ### Roundtop Park Roundtop Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=924439476191731712) ### Cassinelli Winery and Vineyards You can enjoy a tasting or tour at Cassinelli Winery and Vineyards during your travels to Church Hill. Take in the festivals while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879606) ### Rolphs Wharf Marina Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879605) ## Frequently asked questions ### What's the area like around Tilmon's Island Winery? ### Where is the best place to stay near Tilmon's Island Winery? ### How many hotels will I find near Tilmon's Island Winery? ### If I need to cancel the hotel reservation for my stay near Tilmon's Island Winery, will I receive a refund? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [Aberdeen Proving Ground Hotels ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels.d553248634999428212.Travel-Guide-Hotels) - [Apartments in Betterton ](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach ](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - [Cottages in Betterton ](https://www.expedia.ca/Betterton-Cottages.d3000440429-aaCottages.Travel-Guide-Accommodation) - 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