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
CA $1,123
per person
Oct 15 - Oct 18
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Roanoke (ROA)
7.6/10 Good! (1,008 reviews)
Room was clean although very dated. Bed comfortable and price was reasonable with traveling with 2 dogs. Had a nice quiet night and would stay again. Breakfast was not much to write about.
Reviewed on Aug 29, 2026
Quality Inn Dublin I-81
CA $1,221
per person
Oct 15 - Oct 18
found 4 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Roanoke (ROA)
8/10 Very good! (217 reviews)
I like this particular Quality Inn. There is a Mexican restaurant next door that is very good. The pool was broken or closed though. Overall, it is a good deal, pleasant staff and building.
Reviewed on Aug 27, 2026
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The Chessie Trail Hotel Deals
Howard Johnson by Wyndham Lexington
2836 North Lee Highway Lexington VA
Fully refundableReserve now, pay when you stay
CA $83
CA $95 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very good! (1,396 reviews)
"Room was clean. Breakfast was not good and staff were rude and not helpful when the fire alarms went off at 11:00 at night for at least 2 hours!"
Reviewed on Aug 29, 2026
Wingate by Wyndham Lexington
1100 N Lee Hwy Lexington VA
Fully refundableReserve now, pay when you stay
CA $98
CA $113 total
Sep 7 - Sep 8
includes taxes & fees
Sleep Inn & Suites Virginia Horse Center
95 Maury River Rd Lexington VA
Fully refundable
CA $111
CA $128 total
Sep 6 - Sep 7
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Pool snd hot tub were very nice, room large snd beds compy. Breakfast was good snd quick. Friendly staff snd prIce was excellent"
Reviewed on Aug 27, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
