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/1000000/30000/25100/25008/12f7b572_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Newark - Wilmington 65 Geoffrey Dr Newark DE CA $92 CA $102 total Apr 28 - Apr 29 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 ... 5.6/10 (1,002 reviews) Raj was very helpful when I was looking for a fork at 11 pm. Refrigerator in the room was not working although it was plugged in. Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F04%2F2026&endDate=29%2F04%2F2026&selected=25008&PinnedHotelID=25008&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 Fully refundableReserve now, pay when you stay CA $130 CA $144 total May 3 - May 4 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! (1,246 reviews) Location good. Room was not clean, no drain plugs for shower or sink. Breakfast not avail due to hotel changing ownership soon. Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F05%2F2026&endDate=04%2F05%2F2026&selected=2091&PinnedHotelID=2091&HadPinnedHotel=true®ionId=553248635975872164) ![Great Wolf Lodge Perryville](https://images.trvl-media.com/lodging/104000000/103100000/103097900/103097849/31e21486_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Great Wolf Lodge Perryville 1240 Chesapeke Overlook Parkway Perryville MD CA $277 CA $310 total Apr 26 - Apr 27 includes taxes & fees Stay at this hotel in Perryville. Enjoy free WiFi, 4 restaurants, and water park access (surcharge). Popular attractions Hollywood Casino and Garrett Island ... 8.6/10 Excellent! (192 reviews) Yes great stay Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=103097849&PinnedHotelID=103097849&HadPinnedHotel=true®ionId=553248635975872164) [See all 624 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=04%2F04%2F2026&endDate=05%2F04%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. ![5-bedroom vacation home 5 minutes from historic Charlestown](https://images.trvl-media.com/lodging/35000000/34020000/34013500/34013405/w800h599x0y1-14614b8c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 5-bedroom vacation home 5 minutes from historic Charlestown Perryville MD Book a stay at this family-friendly vacation home in Perryville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chestnut Point Estates ... 9.8/10 Exceptional! (148 reviews) This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! Reviewed on Feb 9, 2026 [](https://expedia.ca/Perryville-Hotels-Top-Of-The-Chesapeake-Minutes-From-Historic-Charlestown.h34013405.Hotel-Information) ![Captivating Chesapeake experience](https://images.trvl-media.com/lodging/84000000/83920000/83911600/83911536/d9acb620_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Captivating Chesapeake experience Perryville MD Stay at this vacation home in Perryville. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Chestnut Point Estates and Marina and Craft Haven ... 10/10 Exceptional! (284 reviews) beautiful property overlooking the water, great sunrise views. very clean and well equipped. owner was communicative. will return Reviewed on Mar 16, 2026 [](https://expedia.ca/Perryville-Hotels-Captivating-Chesapeake-Experience.h83911536.Hotel-Information) ![Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD. ](https://images.trvl-media.com/lodging/96000000/95370000/95369800/95369772/63fa0d1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD. Havre de Grace MD Stay at this houseboat in Havre De Grace. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Havre de Grace Maritime Museum ... 9.6/10 Exceptional! (34 reviews) We had a wonderful stay! The home was clean, comfortable, and exactly as described. The host was friendly and easy to communicate with. Perfect location and everything we needed for a relaxing trip. Highly recommend!” Reviewed on Oct 5, 2025 [](https://expedia.ca/Havre-De-Grace-Hotels-Fully-Equipped-Docked-Houseboat-At-Log-Pond-Marina-In-Havre-De-Grace.h95369772.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=2026-04-03&endDate=2026-04-04)[Apr 3 - Apr 4](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-04-03&endDate=2026-04-04) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-04-04&endDate=2026-04-05)[Apr 4 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=2026-04-04&endDate=2026-04-05) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975872164&startDate=03%2F04%2F2026&endDate=05%2F04%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) #### Cow Pond Commune with nature and explore the great outdoors at Cow Pond during your travels in Elkton. While you're here, you can savor the top-notch restaurants. [](https://expedia.ca/Cow-Pond-Elkton.d553248621532663259.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) #### 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) #### Elkton Indoor Tennis Catch an event at Elkton Indoor Tennis during your trip to Elkton. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area. [](https://expedia.ca/Elkton-Indoor-Tennis-Elkton.d553248621532663263.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) ## 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) - [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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