Title: Visit The Chessie Trail: Best of The Chessie Trail Tourism | Expedia Travel Guide - Expedia.ca

[Hotels in The Chessie Trail](https://expedia.ca/The-Chessie-Trail-Hotels.d950881170208768000.Travel-Guide-Hotels)[Vacation Rentals in The Chessie Trail](https://expedia.ca/The-Chessie-Trail-Vacation-Rentals.d950881170208768000.Travel-Guide-VacationRentals)[The Chessie Trail Car Rentals](https://expedia.ca/Car-Rentals-In-The-Chessie-Trail.d950881170208768000.Car-Rental-Guide)[The Chessie Trail Vacation Packages](https://expedia.ca/The-Chessie-Trail.d950881170208768000.Destination-Travel-Guides)

# The Chessie Trail

## Travel Guide

## Visit The Chessie Trail

Things to do

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=DX_SPRING_PROMO_950881170208768000)

- The Chessie Trail Hotel Deals
- Vacation Rentals in The Chessie Trail

![Wingate by Wyndham Lexington](https://images.trvl-media.com/lodging/1000000/700000/699700/699693/2ca17d93_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Wingate by Wyndham Lexington

1100 N Lee Hwy Lexington VA

CA $115

CA $132 total

Mar 4 - Mar 5

includes taxes & fees

Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.2/10 Very Good! (1,001 reviews)

Very nice girl at check-in was very patient and took the time to check and see if I could get an upgrade for being a Diamond member.

Reviewed on Feb 14, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=699693&PinnedHotelID=699693&HadPinnedHotel=true&regionId=950881170208768000)

![Hampton Inn Lexington-Historic District](https://images.trvl-media.com/lodging/1000000/200000/199800/199780/107bd352_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hampton Inn Lexington-Historic District

401 E Nelson St Lexington VA

CA $144

CA $163 total

Mar 4 - Mar 5

includes taxes & fees

Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...

9.2/10 Wonderful! (863 reviews)

very clean room and charming character

Reviewed on Feb 10, 2026

[](https://expedia.ca/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=199780&PinnedHotelID=199780&HadPinnedHotel=true&regionId=950881170208768000)

![Comfort Inn Lexington Virginia Horse Center](https://images.trvl-media.com/lodging/1000000/30000/26000/25909/60c32050_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Comfort Inn Lexington Virginia Horse Center

62 Comfort Way Lexington VA

CA $100

CA $115 total

Feb 25 - Feb 26

includes taxes & fees

Book a stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

8.2/10 Very Good! (881 reviews)

The room was good--what you would expect from a hotel room. The staff was very helpful, particularly the clerk who checked us in. I am very happy with that clerk and her assistance.

Reviewed on Jan 31, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F02%2F2026&endDate=26%2F02%2F2026&selected=25909&PinnedHotelID=25909&HadPinnedHotel=true&regionId=950881170208768000)

[See all 448 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=18%2F02%2F2026&endDate=19%2F02%2F2026&regionId=6056914)

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.

![Autumn Ridge Cottages](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/eef05f2b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Autumn Ridge Cottages

Autumn Ridge Lane Lexington VA

Stay at this cottage in Lexington. Enjoy free WiFi, free parking, and private hot tubs. Our guests praise the property condition in our reviews. Popular attractions ...

9.6/10 Exceptional! (13 reviews)

Ridge View cottage is very nice. Situated at the top of a hill, views are great and wildlife is everywhere!

Reviewed on May 18, 2025

[](https://expedia.ca/Lexington-Hotels-Autumn-Ridge-Cottages.h23559919.Hotel-Information)

![HOT TUB w CA King beds Acres of  & secluded. Pymt plan, dogs welcome](https://images.trvl-media.com/lodging/67000000/66150000/66149900/66149833/16339273_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

HOT TUB w CA King beds Acres of & secluded. Pymt plan, dogs welcome

 Lexington VA

Stay at this vacation home in Lexington. Enjoy free WiFi, a garden, and laundry facilities.

10/10 Exceptional! (116 reviews)

We had a wonderful time! The host was welcoming and checked in to make sure that we had everything we needed. The beds were very comfortable! My favorite thing was the hot tub and being able to just relax while at the cabin. Would definitely recommend and look forward to staying here again.

Reviewed on Jan 1, 2026

[](https://expedia.ca/Lexington-Hotels-Acres-Of-Woods-To-Do-Your-Own-Hiking.h66149833.Hotel-Information)

![Alone Mill Schoolhouse - A paradise for outdoor lovers](https://images.trvl-media.com/lodging/34000000/33490000/33482700/33482638/e2d66e93_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Alone Mill Schoolhouse - A paradise for outdoor lovers

 Lexington VA

Book a stay at this family-friendly vacation home in Lexington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lexington Valley Vineyard ...

9.6/10 Exceptional! (201 reviews)

Stayed there last year, will stay again next year.Host is great. everything is just like she says.

Reviewed on Feb 3, 2026

[](https://expedia.ca/Lexington-Hotels-Alone-Mill-Schoolhouse-Outdoor-Lovers-Paradise.h33482638.Hotel-Information)

[See all 448 properties in Lexington](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6056914&sort=VACATION_RENTAL)

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.

## Check The Chessie Trail hotel availability

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=2026-02-17&endDate=2026-02-18)[Feb 17 - Feb 18](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=2026-02-17&endDate=2026-02-18)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=2026-02-18&endDate=2026-02-19)[Feb 18 - Feb 19](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=2026-02-18&endDate=2026-02-19)

[This weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=950881170208768000&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)

### Popular places to visit

![Virginia Military Institute](https://images.trvl-media.com/place/6140121/9a42eaa7-97ba-4bf4-b4b7-2e18fae2ff12.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Virginia Military Institute

Explore the campus of Virginia Military Institute, during your travels in Lexington. Attend a sporting event in the area, or seek out the horseback riding. 

[](https://expedia.ca/Virginia-Military-Institute-Lexington.d6140121.Vacation-Attraction)

#### Virginia Horse Center

You can take time to visit Virginia Horse Center during your travels to Lexington. Attend a sporting event in the area, or seek out the horseback riding. 

[](https://expedia.ca/Virginia-Horse-Center-Lexington.d6200945.Vacation-Attraction)

#### Washington and Lee University

Enjoy the collegiate vibe when you visit Washington and Lee University, during your travels in Lexington. While you're here, you can savor the top-notch restaurants. 

[](https://expedia.ca/Washington-And-Lee-University-Lexington.d6149792.Vacation-Attraction)

#### VMI Museum

You can study the exhibits at VMI Museum, a museum with a story of its own, during your trip to Lexington. While you're here, you can savor the top-notch restaurants. 

[](https://expedia.ca/VMI-Museum-Lexington.d553248621587586993.Vacation-Attraction)

#### Stonewall Jackson House

Find out about the history of Lexington with a stop at Stonewall Jackson House. While you're here, you can savor the top-notch restaurants. 

[](https://expedia.ca/Stonewall-Jackson-House-Lexington.d6257242.Vacation-Attraction)

#### The Lexington Golf & Country Club

Enjoy a round of golf in Lexington at The Lexington Golf & Country Club. While you're here, you can savor the top-notch restaurants. 

[](https://expedia.ca/The-Lexington-Golf-Country-Club-Lexington.d553248621586065634.Vacation-Attraction)

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- [Car rental Buena Vista ](https://www.expedia.ca/Car-Rentals-In-Buena-Vista.d184088.Car-Rental-Guide)
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- [Things to do in Lexington ](https://www.expedia.ca/Things-To-Do-In-Lexington.d6056914.Travel-Guide-Activities)
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- Cities near The Chessie Trail
- Places of interest

- [Lee Chapel and Museum ](https://expedia.ca/Lee-Chapel-And-Museum-Lexington.d6257240.Vacation-Attraction)

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## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app