Title: The 10 Best Hotels Near Tilmon's Island Winery, Sudlersville from CA $126 | 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Tilmon's Island Winery, Sudlersville from CA $126 ![](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 [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-10-20&endDate=2025-10-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248621532662416&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Top Hotels Close to Tilmon's Island Winery ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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) ![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 18.2 km from Tilmon's Island Winery 8.6/10 Excellent (832) "The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlie CA $143 CA $159 total includes taxes & fees Oct 21 - Oct 22 [](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) ![1 bedroom, desk, laptop workspace, blackout drapes](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 18.1 km from Tilmon's Island Winery 7.2/10 Good (406) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $114 CA $126 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-02&endDate=2025-11-03®ionId=553248621532662416&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Tilmon's Island Winery Hotel Reviews ![Hampton Inn Middletown](//images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe_y.jpg) ### Hampton Inn Middletown 10/10 Excellent "Staff was friendly,Candace." [](https://expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Bally's Dover Casino Resort](//images.trvl-media.com/lodging/2000000/1580000/1573000/1572988/b37bb6df_y.jpg) ### Bally's Dover Casino Resort 10/10 Excellent "The hotel itself is GREAT! It's beautiful and clean and the staff was helpful. I had a large room with a comfortable bed, good TV options, and I was able to get late night food at Odd Bites coffee (or something like that). Very good. I attended a conference there and the food provided to the Conference attendees by the hotel was most excellent! Water, coffee, and hot tea were available all day and iced tea was added at lunch and available the rest of the day. The only things I didn't love about the hotel were that the pillows were horribly uncomfortable and the bath towels were small and hard/stiff. I don't expect luxury, million dollar towels, but for as nice as the hotel was, the towels felt like a cheap afterthought. Otherwise, an excellent stay and I would recommend it! Would definitely stay again! Dover is not a nice area in my opinion. It feels dangerous and unwelcoming. I went to the Burlington just a few blocks down and when I walked it, it was roped off and a security guard came over to let me in and when I questioned him about the random rope gates at the doors he said "people like to steal here" and I asked, "Is that a Dover issue? Does that happen around a lot?" He said it did and it was a big concern for the area. When I went to Panera there was a coded lock on the bathroom door and even going in, the general vibe was dirty and not well cared for. None of this is a reflection of the hotel, but as far as the city goes, I don't love it. " [](https://expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information) ![Red Roof Inn & Suites Dover Downtown](//images.trvl-media.com/lodging/1000000/890000/888000/887960/473c4e31_y.jpg) ### Red Roof Inn & Suites Dover Downtown 10/10 Excellent "Parking was easy. Close to food spots. Rooms are clean. Staff are nice. Hallways spaces are well lit and tidey." [](https://expedia.ca/Dover-Hotels-Red-Roof-Inn-Suites-Dover-Downtown.h887960.Hotel-Information) ![Holiday Inn Express & Suites Middletown by IHG](//images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/82e4e131_y.jpg) ### Holiday Inn Express & Suites Middletown by IHG 10/10 Excellent "Clean and comfortable " [](https://expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Hilton Garden Inn Dover](//images.trvl-media.com/lodging/3000000/2240000/2232400/2232384/eab21539_y.jpg) ### Hilton Garden Inn Dover 10/10 Excellent "No complaints! " [](https://expedia.ca/Dover-Hotels-Hilton-Garden-Inn-Dover.h2232384.Hotel-Information) ![Hampton Inn Dover](//images.trvl-media.com/lodging/1000000/40000/34500/34429/8eb0188e_y.jpg) ### Hampton Inn Dover 10/10 Excellent "Loved it. " [](https://expedia.ca/Dover-Hotels-Hampton-Inn-Dover.h34429.Hotel-Information) ![Home2 Suites by Hilton Dover, DE](//images.trvl-media.com/lodging/1000000/30000/26700/26691/w3837h2558x3y3-b9ccd77d_y.jpg) ### Home2 Suites by Hilton Dover, DE 10/10 Excellent "Staff was friendly and easy to work with " [](https://expedia.ca/Dover-Hotels-Home2-Suites-By-Hilton-Dover.h26691.Hotel-Information) ![Sleep Inn And Suites](//images.trvl-media.com/lodging/3000000/2120000/2115100/2115064/558d764a_y.jpg) ### Sleep Inn And Suites 10/10 Excellent "Very" [](https://expedia.ca/Dover-Hotels-Sleep-Inn-And-Suites.h2115064.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Great service. Very clean." [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Hotels near other Tilmon's Island Winery attractions [](https://www.expedia.ca/Pinkney-Park-Hotels.0-l924440153884332032-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Crumpton-Auction-Hotels.0-l553248621532662415-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Crumpton-Park-Hotels.0-l924439696180879360-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Chase-Island-Hotels.0-l924439142769758208-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Church-Hill-Theatre-Hotels.0-l844528418122231808-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Roundtop-Park-Hotels.0-l924439476191731712-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Cassinelli-Winery-And-Vineyards-Hotels.0-l553248621561879606-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels) ### 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? > Tilmon's Island Winery is located in an area of Sudlersville that travelers like for its university setting. You'll find 12 hotels and other accommodations within a few miles for a convenient home base. ### Where is the best place to stay near Tilmon's Island Winery? > [Red Roof Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) is one of the top choices for your stay based on our traveler data, and this hotel offers free parking and free WiFi. You'll find it 11.3 mi (18.1 km) from Tilmon's Island Winery. Other good choices in the area include [Comfort Inn & Suites Chestertown](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) and [Bally's Dover Casino Resort](https://www.expedia.ca/Dover-Hotels-Dover-Downs-Hotel-Casino.h1572988.Hotel-Information). ### How many hotels will I find near Tilmon's Island Winery? > Expedia has 12 hotels and other accommodations a few miles from 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? > Yes! The majority of hotel room reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If your reservation is non-refundable, you might be able to still cancel and get a refund within 24 hours of your booking. Put your dates in and click on "Search", then use the filter option "fully refundable" to get the top deals on offer near Tilmon's Island Winery. ## 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) - [Betterton Hotels](https://www.expedia.ca/Betterton-Hotels.d3000440429.Travel-Guide-Hotels) - [Resorts in Betterton](https://www.expedia.ca/Betterton-Resort-Hotels.d3000440429-aaResortHotels.Travel-Guide-Accommodation) - [Cecilton Hotels](https://www.expedia.ca/Cecilton-Hotels.d177525.Travel-Guide-Hotels) - 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[Resorts in Warwick](https://www.expedia.ca/Warwick-Resort-Hotels.d553248635975870671-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Washington College](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [B&B in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Bed-And-Breakfast.d553248635975865930-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Cottages.d553248635975865930-aaCottages.Travel-Guide-Accommodation) - [White Crystal Beach Hotels](https://www.expedia.ca/White-Crystal-Beach-Hotels.d553248635975865930.Travel-Guide-Hotels) - [Resorts in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Resort-Hotels.d553248635975865930-aaResortHotels.Travel-Guide-Accommodation) - [Worton Hotels](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels) - [Wye Mills Hotels](https://www.expedia.ca/Wye-Mills-Hotels.d6359185.Travel-Guide-Hotels) - [Flights to Chestertown](https://www.expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights) - [Flights from Kennedyville](https://www.expedia.ca/lp/flights/3000440679/flights-from-kennedyville) - [Flights from Massey](https://www.expedia.ca/lp/flights/3000440702/flights-from-massey) - [Flights from Barclay](https://www.expedia.ca/lp/flights/553248634998993874/flights-from-barclay) - [Flights from Chestertown](https://www.expedia.ca/lp/flights/7215/flights-from-chestertown) - [Flights from Centreville](https://www.expedia.ca/lp/flights/88125/flights-from-centreville) - [Historical Society of Kent County Maryland](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Mount Harmon Plantation](https://www.expedia.ca/Mount-Harmon-Plantation-Earleville.d553248621561879694.Vacation-Attraction) - [Wilmer Park](https://www.expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Budget Rental Cars in Chestertown](https://www.expedia.ca/Budget-Car-Rentals-In-Chestertown.d7215-c39.Car-Rental-Guide-Suppliers) - [Car rental Centreville](https://www.expedia.ca/Car-Rentals-In-Centreville.d88125.Car-Rental-Guide) - [Car rental Chestertown](https://www.expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide) - [Centreville Vacation Rentals](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals)