Title: The Chessie Trail Vacation Packages & Trips 2026 from CA $1,236 | Expedia.ca [The Chessie Trail Travel Guide](https://expedia.ca/The-Chessie-Trail.dx950881170208768000)[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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # The Chessie Trail Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Top The Chessie Trail Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Budget Inn By OYO Natural Bridge I-81](https://images.trvl-media.com/lodging/10000000/9500000/9496200/9496127/c361d3fb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Budget Inn By OYO Natural Bridge I-81 CA $1,236 per person May 12 - May 16 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Roanoke (ROA) 6.4/10 (360 reviews) Great room. Easy online reservation. Friendly clerk. Reviewed on Dec 17, 2025 ![Timberlake Motel](https://images.trvl-media.com/lodging/3000000/2120000/2113400/2113371/6115904c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Timberlake Motel CA $2,138 per person May 12 - May 16 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Lynchburg (LYH) 7.8/10 Good! (924 reviews) Room could be upgraded. Reviewed on Mar 19, 2026 ![Quality Inn Lynchburg near University](https://images.trvl-media.com/lodging/1000000/30000/21100/21061/8548f7ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Quality Inn Lynchburg near University Montview CA $1,959 per person May 12 - May 16 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Lynchburg (LYH) 7.4/10 Good! (876 reviews) Room was cheap for the area. Lobby was clean. The rooms are kind of worn down. Overall for just needed to stay a night it was fine. Reviewed on Mar 16, 2026 ![The Promissory Hotel](https://images.trvl-media.com/lodging/121000000/120690000/120682400/120682373/c10f2f9c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Promissory Hotel Downtown Roanoke CA $1,795 per person May 12 - May 16 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Roanoke (ROA) 9.8/10 Exceptional! (15 reviews) Excellent location. They are working on signage. Enter on Campbell ave. Parking garage is walkable. Great price! Highly recommend. Reviewed on Apr 4, 2026 ![Comfort Inn & Suites Lynchburg Airport - University Area](https://images.trvl-media.com/lodging/12000000/11920000/11919200/11919107/3878b630_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn & Suites Lynchburg Airport - University Area CA $2,158 per person May 12 - May 16 found 9 hours ago Roundtrip flight included Toronto (YYZ) to Lynchburg (LYH) 9.4/10 Exceptional! (1,000 reviews) Internet was fine 10 mbs. Staff was amazingly friendly and helpful! Location excellent and rooms were clean. Reviewed on Apr 3, 2026 ## Ready to book your vacation to The Chessie Trail? Choose your dates ## The Chessie Trail Hotel Deals ![Best Western Lexington Inn](https://images.trvl-media.com/lodging/1000000/30000/24600/24544/a0ea9be7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Lexington Inn 850 N Lee Highway Lexington VA Fully refundableReserve now, pay when you stay CA $99 CA $114 total Apr 20 - Apr 21 includes taxes & fees 8/10 Very Good! (1,001 reviews) The rooms and beds are small. The prices are too high for midweek stays. Reviewed on Apr 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=24544&PinnedHotelID=24544&HadPinnedHotel=true®ionId=950881170208768000) ![Howard Johnson by Wyndham Lexington](https://images.trvl-media.com/lodging/1000000/20000/11000/10961/9f4afb55_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Howard Johnson by Wyndham Lexington 2836 North Lee Highway Lexington VA Fully refundableReserve now, pay when you stay CA $83 CA $96 total Apr 12 - Apr 13 includes taxes & fees 8.2/10 Very Good! (1,342 reviews) Wonderful place from the staff to the rooms with a beautiful view. Definitely Reviewed on Apr 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=10961&PinnedHotelID=10961&HadPinnedHotel=true®ionId=950881170208768000) ![The Gin Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/10000000/9660000/9651600/9651537/0fa2ed47_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Gin Hotel, an Ascend Collection Hotel 30 South Main Street Lexington VA Fully refundable CA $148 CA $184 total Apr 20 - Apr 21 includes taxes & fees 8.6/10 Excellent! (1,002 reviews) We only stayed one night so didn’t utilize amenities or interact with staff much. Good location, free parking. Grab & go breakfast was appropriately named: fruit, granola bars, yogurt etc. The most memorable thing about this hotel unfortunately was the bed and pillows. Quite possibly the most uncomfortable ... Reviewed on Apr 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=20%2F04%2F2026&endDate=21%2F04%2F2026&selected=9651537&PinnedHotelID=9651537&HadPinnedHotel=true®ionId=950881170208768000) [See all 455 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026®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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in The Chessie Trail #### Lee Chapel and Museum You can browse the exhibits at Lee Chapel and 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/Lee-Chapel-And-Museum-Lexington.d6257240.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](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. Scan the QR code with your device camera and download our app