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 $96 CA $110 total Nov 12 - Nov 13 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=12%2F11%2F2025&endDate=13%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 $131 CA $151 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! (1,005 reviews) Convenient to colleges Reviewed on Oct 31, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=24235&PinnedHotelID=24235&HadPinnedHotel=true®ionId=950881170208768000) ![Best Western Lexington Inn](https://images.trvl-media.com/lodging/1000000/30000/24600/24544/67e4e9d7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Lexington Inn 850 N Lee Highway, Lexington, VA CA $101 CA $116 total Nov 23 - Nov 24 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 ... 7.8/10 Good! (1,004 reviews) Na Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%2F2025&selected=24544&PinnedHotelID=24544&HadPinnedHotel=true®ionId=950881170208768000) [See all 431 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=06%2F11%2F2025&endDate=07%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) Fantastic location and such a cozy and nice place! Reviewed on Oct 19, 2025 [](https://expedia.ca/Lexington-Hotels-Lovely-C1890-Flat-With-Garden-In-Historic-Downtown.h41047446.Hotel-Information) ![Newly renovated studio Apartment in Downtown Lexington. 5 min walk to W&L or VMI](https://images.trvl-media.com/lodging/70000000/69920000/69912800/69912789/182253d9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Newly renovated studio Apartment in Downtown Lexington. 5 min walk to W&L or VMI Lexington Stay at this apartment in Lexington. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Stonewall Jackson Grave and Stonewall Jackson House ... 9.8/10 Exceptional! (51 reviews) The apartment was clean and conveniently located in downtown Lexington. The W&L and VMI campuses are within walking distance. It was the perfect size for a couple. Reviewed on Nov 1, 2025 [](https://expedia.ca/Lexington-Hotels-Newly-Renovated-Studio-Apartment-In-Downtown-Lexington-5-Min-Walk-To-WL-Or-VMI.h69912789.Hotel-Information) ![HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome](https://images.trvl-media.com/lodging/67000000/66150000/66149900/66149833/16339273_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome Lexington Stay at this vacation home in Lexington. Enjoy free WiFi, a garden, and laundry facilities. 10/10 Exceptional! (113 reviews) We did not use Hot Tub. There were 3 doggie beds, ( we call them climbs) in the basement, that was a great addition for our dog as she loves to hang out on them. Very pet friendly, very clean. Convenient to Lexington to see all the history in the town. The drive out to the house is awesome, very ... Reviewed on Oct 29, 2025 [](https://expedia.ca/Lexington-Hotels-Acres-Of-Woods-To-Do-Your-Own-Hiking.h66149833.Hotel-Information) [See all 431 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=2025-11-05&endDate=2025-11-06) [Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-05&endDate=2025-11-06)[Nov 5 - Nov 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-05&endDate=2025-11-06) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-06&endDate=2025-11-07) [Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-06&endDate=2025-11-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-06&endDate=2025-11-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-06&endDate=2025-11-07)[Nov 6 - Nov 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=2025-11-06&endDate=2025-11-07) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=07%2F11%2F2025&endDate=09%2F11%2F2025) [This 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) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025)[Nov 14 - Nov 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=950881170208768000&startDate=14%2F11%2F2025&endDate=16%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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[Hotels near Washington and Lee University](https://www.expedia.ca/Washington-And-Lee-University-Hotels.0-l6149792-0.Travel-Guide-Filter-Hotels) - [Flights to Buena Vista](https://www.expedia.ca/Cheap-Flights-To-Buena-Vista.d184088.Travel-Guide-Flights) - [Flights to Lexington](https://www.expedia.ca/Cheap-Flights-To-Lexington.d6056914.Travel-Guide-Flights) - [Flights from Lexington](https://www.expedia.ca/lp/flights/6056914/flights-from-lexington) - [Visit Blue Ridge Tunnel Trail](https://www.expedia.ca/Blue-Ridge-Tunnel-Trail.dx847217400490500096) - [Visit Boones Mill](https://www.expedia.ca/Boones-Mill.dx3000459824) - [Visit Boonesville](https://www.expedia.ca/Boonesville.dx553248635975872343) - [Visit Browntown](https://www.expedia.ca/Browntown.dx553248635975847852) - [Visit Barracks Rugby](https://www.expedia.ca/Charlottesville-Barracks-Rugby.dx553248635976470653) - [Visit Fifeville](https://www.expedia.ca/Charlottesville-Fifeville.dx553248635976468741) - [Visit Fry's Spring](https://www.expedia.ca/Charlottesville-Frys-Spring.dx553248635976476680) - [Visit Lake Reynovia](https://www.expedia.ca/Charlottesville-Lake-Reynovia.dx553248635976469677) - [Visit Charlottesville](https://www.expedia.ca/Charlottesville.dx6057012) - [Visit Coleman Falls](https://www.expedia.ca/Coleman-Falls.dx553248635975866254) - [Visit Daleville](https://www.expedia.ca/Daleville.dx94903) - [Visit Fincastle](https://www.expedia.ca/Fincastle.dx3000459955) - [Visit Fishersville](https://www.expedia.ca/Fishersville.dx602381) - [Visit Gladys](https://www.expedia.ca/Gladys.dx3000459992) - [Visit Goodview](https://www.expedia.ca/Goodview.dx3000460014) - [Visit Mason Cove](https://www.expedia.ca/Mason-Cove.dx553248635975846729) - [Visit Massanetta Springs](https://www.expedia.ca/Massanetta-Springs.dx553248635975865634) - [Visit Moneta](https://www.expedia.ca/Moneta.dx6348084) - [Visit Montvale](https://www.expedia.ca/Montvale.dx6348039) - [Visit Piney Mountain](https://www.expedia.ca/Piney-Mountain.dx553248635976007080) - [Visit Downtown Roanoke](https://www.expedia.ca/Roanoke-Downtown-Roanoke.dx902335776954859520) - [Visit Roanoke](https://www.expedia.ca/Roanoke.dx3020) - [Visit Roseland](https://www.expedia.ca/Roseland.dx6361484) - [Visit Scottsville](https://www.expedia.ca/Scottsville.dx184107) - [Visit Staunton](https://www.expedia.ca/Staunton.dx6056906) - [Visit Timber Ridge](https://www.expedia.ca/Timber-Ridge.dx3000007919) - [Visit Troutville](https://www.expedia.ca/Troutville.dx10009) - [Visit Tyro](https://www.expedia.ca/Tyro.dx3000460704) - [Visit Waynesboro](https://www.expedia.ca/Waynesboro.dx6733) - [Visit Westlake Corner](https://www.expedia.ca/Westlake-Corner.dx6348085) - [Car rental Buena Vista](https://www.expedia.ca/Car-Rentals-In-Buena-Vista.d184088.Car-Rental-Guide) - [Car rental Lexington](https://www.expedia.ca/Car-Rentals-In-Lexington.d6056914.Car-Rental-Guide) - [Things to do in Lexington](https://www.expedia.ca/Things-To-Do-In-Lexington.d6056914.Travel-Guide-Activities) - [Things to do in Rockbridge Baths](https://www.expedia.ca/Things-To-Do-In-Rockbridge-Baths.d3000460645.Travel-Guide-Activities) - 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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