Title: Visit The Chessie Trail: Best of The Chessie Trail Tourism | Expedia Travel Guide - Expedia.ca [Hotels in The Chessie Trail](https://expedia.ca/The-Chessie-Trail-Hotels.d950881170208768000.Travel-Guide-Hotels)[Vacation Rentals in The Chessie Trail](https://expedia.ca/The-Chessie-Trail-Vacation-Rentals.d950881170208768000.Travel-Guide-VacationRentals)[The Chessie Trail Car Rentals](https://expedia.ca/Car-Rentals-In-The-Chessie-Trail.d950881170208768000.Car-Rental-Guide)[The Chessie Trail Vacation Packages](https://expedia.ca/The-Chessie-Trail.d950881170208768000.Destination-Travel-Guides) # The Chessie Trail ## Travel Guide ## Visit The Chessie Trail Things to do - The Chessie Trail Hotel Deals - Vacation Rentals in The Chessie Trail ![Wingate by Wyndham Lexington](https://images.trvl-media.com/lodging/1000000/700000/699700/699693/2ca17d93_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingate by Wyndham Lexington 1100 N Lee Hwy, Lexington, VA Fully refundableReserve now, pay when you stay CA $100 CA $115 total Nov 11 - Nov 12 includes taxes & fees Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ... 8.2/10 Very Good! (1,023 reviews) Clean lobby. Quick check in. Reviewed on Oct 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=699693&PinnedHotelID=699693&HadPinnedHotel=true®ionId=950881170208768000) ![Best Western Plus Inn at Hunt Ridge](https://images.trvl-media.com/lodging/1000000/30000/24300/24235/41c59ed1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Inn at Hunt Ridge 25 Willow Springs Road, Lexington, VA CA $130 CA $150 total Dec 1 - Dec 2 includes taxes & fees Stay at this hotel in Lexington. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ... 8.2/10 Very Good! (1,004 reviews) . Reviewed on Oct 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=24235&PinnedHotelID=24235&HadPinnedHotel=true®ionId=950881170208768000) ![Quality Inn Lexington](https://images.trvl-media.com/lodging/1000000/900000/897400/897380/ec1ccc00_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn Lexington 2809 North Lee Highway, Lexington, VA CA $89 CA $103 total Nov 9 - Nov 10 includes taxes & fees Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ... 6.2/10 (1,025 reviews) The only issue we had was we booked 2 rooms as we were traveling with inlaws. The rooms were not side by side. Had i known this i should have booked them in my name instead of brother inlaws name. The staff was great but nothing they could do upon arrival. Not a big deal but worth mentioning. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=897380&PinnedHotelID=897380&HadPinnedHotel=true®ionId=950881170208768000) [See all 423 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=02%2F11%2F2025&endDate=03%2F11%2F2025®ionId=6056914) 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. ![Lovely C.1890 Flat with Garden in Historic Downtown](https://images.trvl-media.com/lodging/42000000/41050000/41047500/41047446/w568h843x1y1-f1e814c5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lovely C.1890 Flat with Garden in Historic Downtown Lexington Stay at this apartment in Lexington. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Stonewall Jackson Grave and Stonewall Jackson ... 9.6/10 Exceptional! (65 reviews) Ideal location for walking to downtown, nearby trails. Reviewed on Sep 28, 2025 [](https://expedia.ca/Lexington-Hotels-Lovely-C1890-Flat-With-Garden-In-Historic-Downtown.h41047446.Hotel-Information) ![Elegant & Modern Carriage House at Twin Maple Farm](https://images.trvl-media.com/lodging/34000000/33960000/33960000/33959929/3534c964_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elegant & Modern Carriage House at Twin Maple Farm Lexington Stay at this apartment in Lexington. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Lexington Valley Vineyard and Virginia Horse ... 10/10 Exceptional! (182 reviews) We liked our stay very much Reviewed on Oct 23, 2025 [](https://expedia.ca/Lexington-Hotels-Elegant-Modern-Carriage-House-At-Twin-Maple-Farm.h33959929.Hotel-Information) ![Autumn Ridge Cottages](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/eef05f2b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Autumn Ridge Cottages Autumn Ridge Lane, Lexington, VA Stay at this cottage in Lexington. Enjoy free WiFi, free parking, and private hot tubs. Our guests praise the property condition in our reviews. Popular attractions ... 9.6/10 Exceptional! (13 reviews) Ridge View cottage is very nice. Situated at the top of a hill, views are great and wildlife is everywhere! Reviewed on May 18, 2025 [](https://expedia.ca/Lexington-Hotels-Autumn-Ridge-Cottages.h23559919.Hotel-Information) [See all 423 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6056914&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 The Chessie Trail hotel availability [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-01&endDate=2025-11-02) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-01&endDate=2025-11-02) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-01&endDate=2025-11-02) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-01&endDate=2025-11-02)[Nov 1 - Nov 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-01&endDate=2025-11-02) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-02&endDate=2025-11-03) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-02&endDate=2025-11-03) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-02&endDate=2025-11-03) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-02&endDate=2025-11-03)[Nov 2 - Nov 3](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-02&endDate=2025-11-03) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025)[Nov 7 - Nov 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) ### Popular places to visit #### Virginia Military Institute Explore the campus of Virginia Military Institute, during your travels in Lexington. Attend a sporting event in the area, or seek out the horseback riding. [](https://expedia.ca/Virginia-Military-Institute-Lexington.d6140121.Vacation-Attraction) #### Washington and Lee University Enjoy the collegiate vibe when you visit Washington and Lee University, during your travels in Lexington. While you're here, you can savor the top-notch restaurants. [](https://expedia.ca/Washington-And-Lee-University-Lexington.d6149792.Vacation-Attraction) #### Virginia Horse Center You can take time to visit Virginia Horse Center during your travels to Lexington. Attend a sporting event in the area, or seek out the horseback riding. [](https://expedia.ca/Virginia-Horse-Center-Lexington.d6200945.Vacation-Attraction) #### VMI Museum You can study the exhibits at VMI Museum, a museum with a story of its own, during your trip to Lexington. While you're here, you can savor the top-notch restaurants. [](https://expedia.ca/VMI-Museum-Lexington.d553248621587586993.Vacation-Attraction) #### Theatre at Lime Kiln Enjoy a show at Theatre at Lime Kiln, a theater with a story to tell in Lexington. Attend a sporting event in the area, or seek out the horseback riding. [](https://expedia.ca/Theatre-At-Lime-Kiln-Lexington.d553248621532658150.Vacation-Attraction) #### The Lexington Golf & Country Club Enjoy a round of golf in Lexington at The Lexington Golf & Country Club. While you're here, you can savor the top-notch restaurants. 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Cities near The Chessie Trail - Places of interest - [Lee Chapel and Museum](https://expedia.ca/Lee-Chapel-And-Museum-Lexington.d6257240.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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