Title: Visit Winchester: Best of Winchester Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975872164.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975872164.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975872164.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975872164.Destination-Travel-Guides) # Winchester ## Travel Guide ## Visit Winchester Things to do - Winchester Hotel Deals - Vacation Rentals in Winchester ![Quality Inn Newark - Wilmington](https://images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Newark - Wilmington 65 Geoffrey Dr Newark DE CA $82 CA $91 total Feb 28 - Mar 1 includes taxes & fees Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Christiana Mall and Gallaher ... 5.2/10 (1,007 reviews) Nice staff, room quiet Reviewed on Feb 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=25008&PinnedHotelID=25008&HadPinnedHotel=true®ionId=553248635975872164) ![Sheraton Suites Wilmington Downtown](https://images.trvl-media.com/lodging/1000000/10000/4700/4693/72ec9ef5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sheraton Suites Wilmington Downtown 422 Delaware Ave Wilmington DE CA $173 CA $190 total Feb 15 - Feb 16 includes taxes & fees Book a stay at this business-friendly hotel in Wilmington. Enjoy free WiFi, a free area shuttle, and room service. Our guests praise the helpful staff in our ... 8.2/10 Very Good! (1,004 reviews) Always the best place with early check in. Clean and cozy with super awesome customer service. Reviewed on Jan 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=4693&PinnedHotelID=4693&HadPinnedHotel=true®ionId=553248635975872164) ![Sonesta Select Newark Christiana Mall](https://images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta Select Newark Christiana Mall 48 Geoffrey Dr Newark DE CA $126 CA $139 total Feb 28 - Mar 1 includes taxes & fees Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ... 7.6/10 Good! (1,252 reviews) Stay was good aside from the renovations they were doing. we had no water and then no hot water for an extended period of time. and with myself being an essential worker it was a hinderance Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=2091&PinnedHotelID=2091&HadPinnedHotel=true®ionId=553248635975872164) [See all 641 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®ionId=553248635975872164) 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. ![Lancaster co. farmhouse in the heart of amish country](https://images.trvl-media.com/lodging/36000000/35300000/35291700/35291680/91eddd41_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lancaster co. farmhouse in the heart of amish country Christiana PA Book a stay at this family-friendly vacation home in Kirkwood. Enjoy a garden, laundry facilities, and bicycle rentals on site. Popular attractions Wolf's Hollow ... 10/10 Exceptional! (140 reviews) This property is so relaxing and scenic. The farmhouse is luxuriously renovated but feels like stepping back in time all at once. Our family adores seeing the animals on the farm, the peace and quiet, and enjoying family time in the comfy living spaces. We will be back! Reviewed on Dec 22, 2025 [](https://expedia.ca/Kirkwood-Hotels-Lancaster-Co-Home-In-The-Heart-Of-Amish-Country.h35291680.Hotel-Information) ![Chesapeake Bay House with Dock & Private Beach](https://images.trvl-media.com/lodging/34000000/33490000/33484100/33484099/73e9cabf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Bay House with Dock & Private Beach Elkton MD Book a stay at this beach vacation home in Elkton. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions Chesland Park and Brantwood Park ... 10/10 Exceptional! (181 reviews) This VRBO experience was a testament to how VRBO experiences should be. Check in was super easy. Communication was timely and superb. One issue arose which was outside of the host's control and it was dealt with quickly and without impact to the stay. Who can ask for more in that situation. This ... Reviewed on Dec 11, 2025 [](https://expedia.ca/Elkton-Hotels-Chesapeake-Bay-House-With-Dock-Private-Beach.h33484099.Hotel-Information) ![Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!](https://images.trvl-media.com/lodging/118000000/117420000/117414100/117414082/3aedc0b3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun! Chesapeake City MD Stay at this vacation home in Chesapeake City. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Ferryslip Road Park and South Chesapeake ... 10/10 Exceptional! (2 reviews) Tina and Drew were amazing hosts who went above and beyond to make our stay perfect. Their property is absolutely lovely—beautifully maintained, comfortable, old charm and in a great location. We were in town for a wedding and had a wonderful weekend with our family. Tina and Drew were also incredibly ... Reviewed on Oct 28, 2025 [](https://expedia.ca/Chesapeake-City-Hotels-Charming-Queen-Of-Chesapeake-City.h117414082.Hotel-Information) [See all properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635975872164&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-02-10&endDate=2026-02-11) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-02-11&endDate=2026-02-12) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) ### Popular places to visit #### Fair Hill State Natural Resources Management Area Explore the great outdoors at Fair Hill State Natural Resources Management Area, a lovely green space in Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.ca/Fair-Hill-State-Natural-Resources-Management-Area-Elkton.d6187511.Vacation-Attraction) #### Union Hospital Though Union Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Elkton while you are here. [](https://expedia.ca/Union-Hospital-Elkton.d6288957.Vacation-Attraction) #### Fair Hill Equestrian Center You can take time to visit Fair Hill Equestrian Center during your travels to Fair Hill. [](https://expedia.ca/Fair-Hill-Equestrian-Center-Elkton.d974063198074593280.Vacation-Attraction) #### Historical Society of Cecil County You can spend time studying the exhibits at Historical Society of Cecil County during your trip to Elkton. While you're here, you can savor the top-notch restaurants. [](https://expedia.ca/Historical-Society-Of-Cecil-County-Elkton.d553248621561879715.Vacation-Attraction) #### Patriots Glen Golf Club Enjoy a round of golf in Elkton at Patriots Glen Golf Club. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.ca/Patriots-Glen-Golf-Club-Elkton.d553248621532663262.Vacation-Attraction) #### Chesland Park Chesland Park is just one of the places to see in Elkton, so why not enjoy the other things to explore during your travels? Stroll along this family-friendly area's riverfront, or simply enjoy its restaurants. [](https://expedia.ca/Chesland-Park-Elkton.d924439720883253248.Vacation-Attraction) ## Cities near Winchester ![Turkey Point Lighthouse, Elk Neck State Park, Maryland, USA, North East, Maryland](https://images.trvl-media.com/place/7834/75da18a2-d62c-45af-b7c7-16b51512a98a.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Elkton - Cities near Winchester - Places of interest [Elkton](https://expedia.ca/Elkton.dx7834) - [Delaware Park Racetrack and Slots ](https://expedia.ca/Delaware-Park-Racetrack-And-Slots-Wilmington.d6187636.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.ca/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Nemours Mansion and Gardens ](https://expedia.ca/Nemours-Mansion-And-Gardens-Wilmington.d6187486.Vacation-Attraction) - [Chase Center on the Riverfront ](https://expedia.ca/Chase-Center-On-The-Riverfront-Riverfront.d553248634001355599.Vacation-Attraction) - [Bulle Rock Golf Course ](https://expedia.ca/Bulle-Rock-Golf-Course-Havre-De-Grace.d6091695.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.ca/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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