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.
2.5-star property
Clarion Pointe Staunton East
8.6/10 Excellent! (1,007 reviews)
Nov 13 - Nov 15
2 night stay
Chicago (ORD) to Weyers Cave (SHD)
American Airlines • Roundtrip • Coach
Price was $449, price is now $436 per person
$436
per person
found 19 hours ago
The rooms were a little cramped, don't sit in the desk chairs LOL, but the beds were VERY comfortable.
Reviewed on Sep 14, 2026
2.5-star property
Massanutten Resort
8/10 Very Good! (1,522 reviews)
Nov 13 - Nov 15
2 night stay
Chicago (ORD) to Weyers Cave (SHD)
American Airlines • Roundtrip • Coach
Price was $529, price is now $473 per person
$473
per person
found 19 hours ago
Nice room layout with the bathroom accessible from the bedroom and the kitchen.
Reviewed on Sep 14, 2026
Top rated hotels for your The Chessie Trail vacation package
Howard Johnson by Wyndham Lexington
2836 North Lee Highway Lexington VA
Free Cancellation
Reserve now, pay when you stay
5.46 mi from city center
$60 nightly
The price is $69 total per night
$69 total
Sep 21 - Sep 22
Total with taxes and fees
At Howard Johnson by Wyndham Lexington, guests have access to a 24-hour gym, free WiFi in public areas, and conference space. There's free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include a business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included
Sleep Inn & Suites Virginia Horse Center
95 Maury River Rd Lexington VA
Free Cancellation
2.01 mi from city center
$76 nightly
The price is $87 total per night
$87 total
Oct 4 - Oct 5
Total with taxes and fees
At Sleep Inn & Suites Virginia Horse Center, guests have access to an indoor pool, free WiFi in public areas, and conference space. A stay here includes free parking. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include a computer station, free newspapers, and laundry facilities.
Pool
Breakfast included
Best Western Lexington Inn
850 N Lee Highway Lexington VA
Free Cancellation
Reserve now, pay when you stay
1.61 mi from city center
$69 nightly
The price is $79 total per night
$79 total
Sep 27 - Sep 28
Total with taxes and fees
Renovated in 2025, Best Western Lexington Inn offers a gym, free WiFi in public areas, and a business center. A stay here includes free parking. Front-desk staff can answer questions 24/7, and assist with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a computer station, express check-out, and free newspapers.
Breakfast included
Pet friendly
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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