The Chessie Trail Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top The Chessie Trail vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
The Summit at Massanutten Resort by Tripforth
9.2/10 Wonderful! (89 reviews)
Oct 28 - Nov 3
6 night stay
Milwaukee (MKE) to Weyers Cave (SHD)
United • Non-stop roundtrip • Coach
Price was $1,190, price is now $1,060 per person
$1,060
per person
found 1 day ago
Great views. King size sheets on twin beds was annoying.
Reviewed on Aug 29, 2026
4.0-star property
The Liberty Trust
Downtown Roanoke
9.2/10 Wonderful! (1,326 reviews)
Nov 25 - Nov 29
4 night stay
Milwaukee (MKE) to Roanoke (ROA)
American Airlines • Non-stop roundtrip • Coach
Price was $1,204, price is now $1,085 per person
$1,085
per person
found 21 hours ago
Only complaint , hand towel at sink looked used and dirty
Reviewed on Sep 16, 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
$63 nightly
The price is $69 total per night
$69 total
Sep 23 - Sep 24
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.
Explore More Ways to Travel with Travelocity
- Apartments in Buena Vista
- Cabin Rentals in Buena Vista
- Pet Friendly Hotels in Buena Vista
- Buena Vista Hotels
- Vacation Homes in Buena Vista
- Rv Parks in Buena Vista
- Hotels near Washington and Lee University
- Hotels near Virginia Horse Center
- 4 Star Hotels in Lexington
- Farmstay in Lexington
- Apartments in Lexington
- B&B in Lexington
- Cabin Rentals in Lexington
- Beach Resorts & in Lexington
- Boutique Hotels in Lexington
- Cheap Hotels in Lexington
- Business Hotels in Lexington
- Kid Friendly Hotels in Lexington
- Gay Friendly Hotels in Lexington
- Golf Resorts & in Lexington
- Historic Hotels in Lexington
- Hotels with Pool in Lexington
- Hotels with Balconies in Lexington
- Hotels with Bar in Lexington
- Hotels with Free Breakfast in Lexington
- Hotels with Hot Tubs in Lexington
- Hotels with an Indoor Pool in Lexington
- Luxury Hotels in Lexington
- Pet Friendly Hotels in Lexington
- Romantic Getaways & Hotels in Lexington
- Ski Resorts & in Lexington
- Spa Resorts & in Lexington
- Hotels with a Wedding Venue in Lexington
- Winery Hotels in Lexington
- Lexington Hotels
- Inns in Lexington
- Lodges in Lexington
- Motels in Lexington
- Town Houses in Lexington
- Hotels near Southern Virginia University
- Hotels near Lee Chapel and Museum
- Hotels near Virginia Military Institute
- Hotels near Boxerwood Gardens
- Hotels near VMI Museum
- Hotels near Stonewall Jackson Grave
- Hotels near The Lexington Golf & Country Club
- Hotels near Stonewall Jackson Memorial Cemetery
- Hotels near Stonewall Jackson House
- Flights from Atlanta to Buena Vista
- Flights from Boston to Buena Vista
- Flights from Dallas to Buena Vista
- Flights from Denver to Buena Vista
- Flights from Los Angeles to Buena Vista
- Flights from Minneapolis - St. Paul to Buena Vista
- Flights from Salt Lake City to Buena Vista
- Flights from Durango to Buena Vista
- Flights from Portland to Buena Vista
- Flights from Buena Vista
- Flights from Myrtle Beach to Buena Vista
- Flights from Newark to Buena Vista
- Flights from Spokane to Buena Vista
- Flights from Grand Rapids to Buena Vista
- Flights from Rapid City to Buena Vista
- Flights from Bozeman to Buena Vista
- Flights to Lexington
- Flights from Newark to Lexington
- Flights from Lexington
- Buena Vista Vacations
- The Toy Museum at Natural Bridge of Virginia
- Winton Country Club
- Lyndhurst Vacations
- Natural Bridge Zoo
- Natural Bridge Caverns
- Lynchburg Vacations
- Lexington Vacations
- Goode Vacations
- Staunton Vacations
- American Shakespeare Center
- Bold Rock Hard Cider Nellysford Cidery
- Natural Bridge Vacations
- Arrington Vacations
- Montebello Vacations
- Miller Center
- Forest Vacations
- Wintergreen Vacations
- Millboro Springs Vacations
- Nellysford Vacations
- Stuarts Draft Vacations
- Virginia Safari Park
- Eagle Rock Vacations
- Raven's Roost Overlook
- Clifton Forge Vacations
- Wintergreen Resort
- Stoney Creek Golf Course
- Swoope Vacations
- Hot Springs Vacations
- Goshen Pass Natural Area Preserve
