
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.

3.0-star property
Holiday Inn Staunton Conference Center by IHG
8.2/10 Very Good! (1,011 reviews)
Aug 11 - Aug 15
4 night stay
Tampa (TPA) to Weyers Cave (SHD)
American Airlines • Non-stop roundtrip • Coach
Price was $528, price is now $442 per person
$442
per person
found 1 day ago
The restaurant on sight is very sporadic and depends on available employment. When the restaurant is open, this place is great! It’s our go to pit stop between Tennessee and New York. Everyone is so friendly here, and if the restaurant isn’t open, there are numerous choices just a short drive away and some even deliver to the hotel. All in all we love this place and definitely recommend it. If you have kids, they have an indoor pool and if you have pets they are welcome in certain rooms. Very convenient!
Reviewed on Dec 1, 2024

2.5-star property
Colony House Motor Lodge
Franklin-Colonial
9.8/10 Exceptional! (106 reviews)
Jul 11 - Jul 17
6 night stay
Denver (DEN) to Roanoke (ROA)
American Airlines • Non-stop roundtrip • Coach
Price was $964, price is now $810 per person
$810
per person
found 17 hours ago
Great remodeled room me and wife really enjoyed our stay
Reviewed on Dec 31, 2025


3.5-star property
The Lofts at Downtown Salem
9.6/10 Exceptional! (385 reviews)
Jul 11 - Jul 17
6 night stay
Denver (DEN) to Roanoke (ROA)
American Airlines • Non-stop roundtrip • Coach
Price was $910, price is now $773 per person
$773
per person
found 17 hours ago
Nice change from the usual hotel room.
Reviewed on Oct 2, 2025
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
Jun 7 - Jun 8
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 securing valuables and luggage storage. Additional amenities include a business center, a seasonal outdoor pool, and coffee/tea in a common area.
Pool
Breakfast included

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
$91 nightly
The price is $105 total per night
$105 total
Jun 8 - Jun 9
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, luggage storage, and dry cleaning/laundry. Additional amenities include a 24-hour business center, a seasonal outdoor pool, and a computer station.
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
$95 nightly
The price is $110 total per night
$110 total
Jun 11 - Jun 12
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, luggage storage, and securing valuables. 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.
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









