The Chessie Trail Vacation Packages
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Top The Chessie Trail Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Roanoke/Hollins Near I-81
Alpine Hills
Price was CA $779, price is now CA $769 per person
CA $769
per person
Jul 2 - Jul 3
found 2 hours ago
Roundtrip flight included
Edmonton (YEG) to Roanoke (ROA)
7.6/10 Good! (1,020 reviews)
Enjoyed continental breakfast. Was easy to extend my stay.
Reviewed on May 15, 2026
The Liberty Trust
Downtown Roanoke
Price was CA $834, price is now CA $823 per person
CA $823
per person
Jul 2 - Jul 3
found 2 hours ago
Roundtrip flight included
Edmonton (YEG) to Roanoke (ROA)
9.2/10 Wonderful! (1,329 reviews)
Great location for food, shopping and getting to know this part of the city. Felt safe walking everywhere.
Reviewed on May 26, 2026
The West End Flats
West End
Price was CA $810, price is now CA $802 per person
CA $802
per person
Jul 2 - Jul 3
found 2 hours ago
Roundtrip flight included
Edmonton (YEG) to Roanoke (ROA)
9.4/10 Exceptional! (122 reviews)
It's a beautiful space. The host was super helpful. Check in and check out was easy. The location is great. We visited several local restaurants and the transportation museum because of the informational packet within the unit. We would definitely stay again and recommend this place to our friends and family.
Reviewed on May 18, 2026
Fire Station One Boutique Hotel
Downtown Roanoke
Price was CA $946, price is now CA $937 per person
CA $937
per person
Jul 2 - Jul 3
found 2 hours ago
Roundtrip flight included
Edmonton (YEG) to Roanoke (ROA)
9.8/10 Exceptional! (114 reviews)
Gorgeous and chic hotel, walkable to any downtown location that you’d want! Staff is top notch and the furniture is awesome and is for purchase along with some other decor. Drinks are awesome at the bar, along with the appetizers! My date thoroughly enjoyed our stay and we both woukd highly recommend this unique experience
Reviewed on May 19, 2026
The Chessie Trail Hotel Deals
Howard Johnson by Wyndham Lexington
2836 North Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from Jun 10 to Jun 11
CA $82
CA $95 total
Jun 10 - Jun 11
includes taxes & fees
8.2/10 Very Good! (1,345 reviews)
"Good"
Reviewed on May 27, 2026
Best Western Lexington Inn
850 N Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Jun 28 to Jun 29
CA $99
CA $114 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"The staff was very friendly . The place was clean and the bed was comfortable"
Reviewed on May 23, 2026
Comfort Inn Lexington Virginia Horse Center
62 Comfort Way Lexington VA
Fully refundableReserve now, pay when you stay
The price is CA $100 per night from Jun 28 to Jun 29
CA $100
CA $115 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (915 reviews)
"We had a pleasant stay. Quiet and good for families. The staff were friendly and nice. It was convenient for the highway and downtown access. Rooms were good - well maintained and well equipped. Breakfast seemed to be good but we left before we were able to enjoy breakfast. Two criticisms are: hallway ..."
Reviewed on May 19, 2026
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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
