The Chessie Trail Vacation Packages
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Top The Chessie Trail vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Liberty Trust
Downtown Roanoke
9.2/10 Wonderful! (1,254 reviews)
Nov 21 - Nov 23
2 night stay
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
United • Non-stop roundtrip • Coach
Price was $949, price is now $827 per person
$827
per person
found 1 day ago
Loved the old time feel
Reviewed on Aug 4, 2025
2.0-star property
Fire Station One Boutique Hotel
Downtown Roanoke
9.6/10 Exceptional! (104 reviews)
Nov 21 - Nov 23
2 night stay
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
United • Non-stop roundtrip • Coach
Price was $891, price is now $844 per person
$844
per person
found 1 day ago
Awesome and unique spot.
Reviewed on Apr 5, 2024
2.5-star property
Affordable Corporate Suites of Overland Drive
9.4/10 Exceptional! (306 reviews)
Nov 21 - Nov 23
2 night stay
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
United • Non-stop roundtrip • Coach
Price was $742, price is now $714 per person
$714
per person
found 1 day ago
Great place! Easy checking, friendly employees, clean, very quiet!! Queen bed exceptionally comfortable! Will stay again!
Reviewed on Oct 15, 2023
3.5-star property
The Lofts at Downtown Salem
9.6/10 Exceptional! (331 reviews)
Nov 21 - Nov 23
2 night stay
Newark Liberty Intl. Airport (EWR) to Roanoke (ROA)
United • Non-stop roundtrip • Coach
Price was $869, price is now $837 per person
$837
per person
found 1 day ago
Nice change from the usual hotel room.
Reviewed on Oct 2, 2025
Top rated hotels for your The Chessie Trail vacation package
Best Western Plus Inn at Hunt Ridge
25 Willow Springs Road, Lexington, VA
Free Cancellation
Reserve now, pay when you stay
2.1 mi from city center
$105 nightly
The price is $122 total per night
$122 total
Nov 3 - Nov 4
Total with taxes and fees
At Best Western Plus Inn at Hunt Ridge, guests enjoy an indoor pool, a gym, and free WiFi in public areas. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and a computer station.
Pool
Breakfast included
Quality Inn Lexington
2809 North Lee Highway, Lexington, VA
Free Cancellation
Reserve now, pay when you stay
5.42 mi from city center
$64 nightly
The price is $74 total per night
$74 total
Oct 26 - Oct 27
Total with taxes and fees
At Quality Inn Lexington, guests have access to a 24-hour business center, a computer station, and a vending machine. There's free parking if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a picnic area and barbecue grills.
Pool
Breakfast included
Wingate by Wyndham Lexington
1100 N Lee Hwy, Lexington, VA
Free Cancellation
Reserve now, pay when you stay
2.13 mi from city center
$77 nightly
The price is $88 total per night
$88 total
Oct 20 - Oct 21
Total with taxes and fees
At Wingate by Wyndham Lexington, guests have access to an indoor pool, free WiFi in public areas, and a hot tub. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pool
Hot Tub
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.
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