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
Massanutten Resort
8/10 Very Good! (1,253 reviews)
May 16 - May 18
2 night stay
Houston (IAH) to Weyers Cave (SHD)
United • Non-stop roundtrip • Coach
Price was $614, price is now $591 per person
$591
per person
found 1 day ago
Spacious, clean, comfortable and reasonably priced place to stay near our kid's school for parents' weekend.
Reviewed on Oct 4, 2025
3.0-star property
Cave Hill Farm Bed & Breakfast
9.4/10 Exceptional! (340 reviews)
May 16 - May 18
2 night stay
Houston (IAH) to Weyers Cave (SHD)
United • Non-stop roundtrip • Coach
Price was $698, price is now $685 per person
$685
per person
found 1 day ago
Wow Jordan and her husband are great hosts. The have all the extras. Great rooms, homemade snacks, homemade breakfast. The stay could not have gone better and we would definitely stay there again. Best B&B experience I ever had and there have been many over the years.
Reviewed on Feb 19, 2024
Top rated hotels for your The Chessie Trail vacation package
Best Western Lexington Inn
850 N Lee Highway Lexington VA
Free Cancellation
Reserve now, pay when you stay
1.61 mi from city center
$68 nightly
The price is $78 total per night
$78 total
Mar 29 - Mar 30
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 securing valuables, dry cleaning/laundry, and luggage storage. 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-in, and express check-out.
Breakfast included
Pet friendly
Hampton Inn Lexington-Historic District
401 E Nelson St Lexington VA
Free Cancellation
Reserve now, pay when you stay
0.33 mi from city center
$106 nightly
The price is $120 total per night
$120 total
Apr 1 - Apr 2
Total with taxes and fees
Hampton Inn Lexington-Historic District offers a gym, free WiFi in public areas, and a hot tub. Free parking is included with your stay. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Hot Tub
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
$58 nightly
The price is $67 total per night
$67 total
Apr 19 - Apr 20
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
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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