Title: The Chessie Trail Vacation Rentals from CA $265: Short-Term Rentals for 2025 | Expedia.ca

  

[The Chessie Trail Travel Guide](https://expedia.ca/The-Chessie-Trail.dx950881170208768000)[Hotels in The Chessie Trail](https://expedia.ca/The-Chessie-Trail-Hotels.d950881170208768000.Travel-Guide-Hotels)[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)

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# The Chessie Trail Vacation Rentals

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## Check prices for these dates

Tonight

[Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=950881170208768000&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=950881170208768000&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=950881170208768000&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=950881170208768000&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in The Chessie Trail

![Property grounds](https://images.trvl-media.com/lodging/102000000/101510000/101508200/101508135/8a7b79d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101510000/101508200/101508135/f6a5e962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, DVD player, books](https://images.trvl-media.com/lodging/102000000/101510000/101508200/101508135/7230f646.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/102000000/101510000/101508200/101508135/3fc3cefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Whimsical Creekside Cabin

Vesuvius

10/10

Exceptional

(32)

"Had a very quiet relaxing stay "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Joyce I.

CA $89

CA $247 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Vesuvius-Hotels-Whimsical-Creekside-Cabin.h101508135.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99870000/99865600/99865565/0d546018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99870000/99865600/99865565/e86796cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/100000000/99870000/99865600/99865565/b61f260c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99870000/99865600/99865565/9d486179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cape Cod Bungalow @Firmstone Manor

Clifton Forge

9.8/10

Exceptional

(7)

"We enjoyed the serenity of this place and the excellent personal service by the owners. Vkr., Hardy"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hardy

CA $176

CA $225 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Clifton-Forge-Hotels-Cape-Cod-Firmstone-Manor.h99865565.Hotel-Information)

![Deerfield Cottage](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/eef05f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ridgeview Cottage | Private kitchen](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/9eba7118.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ridgeview Cottage | Living area](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/509c28a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Twinleaf Cottage | Terrace/patio](https://images.trvl-media.com/lodging/24000000/23560000/23560000/23559919/a0b58636.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Autumn Ridge Cottages

Lexington

9.0/10

Wonderful

(180)

"Very nicely appointed, clean, quiet, quaint, and close to family. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Gary

CA $370

CA $587 total

includes taxes & fees

Nov 2 - Nov 3

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

![Exterior](https://images.trvl-media.com/lodging/118000000/117520000/117515900/117515839/w905h683x60y0-70753895.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117520000/117515900/117515839/w907h683x58y0-bf6b6543.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117520000/117515900/117515839/w906h683x58y0-11d705e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117520000/117515900/117515839/w902h683x61y0-b4420d58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Woodland Cottage charming 2 bedoom one bath with deck on back, covered front

Buena Vista

9.8/10

Exceptional

(10)

"Very nice and clean property in a quiet neighborhood. Host communicated well and left many amenities for us. Loved our stay!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tina F.

CA $139

CA $265 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Buena-Vista-Hotels-The-Woodland-Cottage-Charming-2-Bedoom-One-Bath-With-Deck-On-Back.h117515839.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109930000/109922300/109922235/b78ab7be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109930000/109922300/109922235/76926f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/110000000/109930000/109922300/109922235/5954dd75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/110000000/109930000/109922300/109922235/56f22087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Simple & spacious 1-bedroom basement living in Lexington. Close to W&L and VMI

Lexington

10/10

Exceptional

(4)

"Great location, cozy, quiet. Great accommodations "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kristen H.

CA $126

CA $196 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lexington-Hotels-Simple-Spacious-1-Bedroom-Basement-Living-In-Lexington-Close-To-WL-And-VMI.h109922235.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/28000000/27140000/27130400/27130301/39cf4b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27140000/27130400/27130301/8e6bda81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/28000000/27140000/27130400/27130301/40f21e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27140000/27130400/27130301/9fd9e494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Deerfield Honeymoon Cottage at Autumn Ridge

Lexington

9.8/10

Exceptional

(39)

"Loved the space and amenities. Super clean for a cabin, and lots of stuff clearly labeled and well organized. Just minutes from downtown Lexington and suburban conveniences while offering easy access to all kinds of Shenandoah. Would definitely stay again! Thank you!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Timothy M.

CA $282

CA $504 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lexington-Hotels-Deerfield-Honeymoon-Cottage-At-Autumn-Ridge.h27130301.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108990000/108980500/108980461/43c84c70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108990000/108980500/108980461/d47d4f8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108990000/108980500/108980461/bf56a060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108990000/108980500/108980461/cf08fbdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming downtown Lex cottage, walk to WLU, VMI

Lexington

10/10

Exceptional

(9)

"The cottage was very comfortable and the check in and check out process was very easy. It was also super clean and air conditioned. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jacqueline B.

CA $198

CA $481 total

includes taxes & fees

Nov 17 - Nov 18

[](https://www.expedia.ca/Lexington-Hotels-Charming-Downtown-Lex-Cottage.h108980461.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/105000000/104250000/104247600/104247530/ab6b6b98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104250000/104247600/104247530/34e36dc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104250000/104247600/104247530/b24f3a02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104250000/104247600/104247530/f04a2687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New Blue RIdge Mountains Montebello, Virginia with stary stary skies

Montebello

10/10

Exceptional

(18)

"Great cabin in a lovely setting. Spent hours sitting outside by the river. Flawless check-in. Great host communication throughout."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan D.

CA $202

CA $321 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Montebello-Hotels-New-Blue-RIdge-Mountains-Montebello.h104247530.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/92db2d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/411a7c25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/48a73253.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104790000/104787300/104787285/08c83ebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Montebello

9.8/10

Exceptional

(16)

"Cabin was clean and tidy. Everything i needed was there. I felt comfortable and safe. This is important because I was traveling alone. This feels like it will be my get away spot in the future. Host was polite and quick to respond"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lori M.

CA $202

CA $316 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Montebello-Hotels-5-Minutes-To-Blue-Ridge-Parkway.h104787285.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/73239ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/3ef8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/c84e0b9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104260000/104258500/104258489/33c95369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello

10/10

Exceptional

(37)

"Great property and host"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher B.

CA $202

CA $316 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Montebello-Hotels-Beautiful-New-Cabins-Mile-Off-Blue-Ridge-Parkway-In-Montebello.h104258489.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/79000000/78160000/78152200/78152174/7e195614.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/79000000/78160000/78152200/78152174/1c9aa3e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78160000/78152200/78152174/7b68eed7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78160000/78152200/78152174/28a90aae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rustic Mountain Home w Theater Room & Fire Pit, Minutes to SVU, W&L, & VMI

Buena Vista

8.8/10

Excellent

(31)

"I didn’t realize that this was an entire house with full kitchen, and two bedrooms. A wonderful place near Buena Vista and Lexington."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matthew

CA $124

CA $298 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Buena-Vista-Hotels-Updated.h78152174.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941685/68712676.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941685/486fb13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941685/585f15bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/105000000/104950000/104941700/104941685/1f761814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hays Creek Cottage: Waterfront Home Near Mountains

Rockbridge Baths

9.4/10

Exceptional

(3)

"Very nice getaway. Clean peaceful, everything I wanted."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Steve H.

CA $222

CA $589 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Rockbridge-Baths-Hotels-Hays-Creek-Cottage-Waterfront-Home-Near-Mountains.h104941685.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102490000/102488000/102487957/fecd725e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102490000/102488000/102487957/30118bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/103000000/102490000/102488000/102487957/02f345f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, shampoo](https://images.trvl-media.com/lodging/103000000/102490000/102488000/102487957/143983b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sweet Upstairs’s apartment right next to Southern Virginia University.

Buena Vista

10/10

Exceptional

(24)

"Just as described. Cozy spot to spend a few days while we attended a wedding and visited family. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lorrie H.

CA $138

CA $200 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/Buena-Vista-Hotels-Sweet-Upstairss-Apartment-Right-Next-To-Southern-Virginia-University.h102487957.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33960000/33960000/33959929/3534c964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33960000/33960000/33959929/4186af73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/34000000/33960000/33960000/33959929/65af154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33960000/33960000/33959929/a107e27e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Elegant & Modern Carriage House at Twin Maple Farm

Lexington

10/10

Exceptional

(207)

"Very pleasant stay -- had everything we needed and very quiet. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer M.

CA $216

CA $317 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lexington-Hotels-Elegant-Modern-Carriage-House-At-Twin-Maple-Farm.h33959929.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129891/c86587ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129891/17df156d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129891/w1167h779x0y0-4e9df225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27130000/27129900/27129891/cfdc301b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rustic Romantic Bayberry Cottage at Autumn Ridge

Lexington

9.6/10

Exceptional

(29)

"Loved our stay! The location is beautiful and the cottage is very private. The front porch has lovely rocking chairs and candles - perfect for watching the sunset or relaxing in the evening."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Hannah Y.

CA $289

CA $513 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Lexington-Hotels-Rustic-Romantic-Bayberry-Cottage-At-Autumn-Ridge.h27129891.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37920000/37915100/37915078/9c1ea4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/38000000/37920000/37915100/37915078/1bfd3c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37920000/37915100/37915078/e6085740.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37920000/37915100/37915078/f7c53b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Twinleaf Honeymoon Cottage at Autumn Ridge

Lexington

9.8/10

Exceptional

(13)

"Great location. Very quiet and clean. A great stay!!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Erik T.

CA $282

CA $504 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lexington-Hotels-Twinleaf-Honeymoon-Cottage-At-Autumn-Ridge.h37915078.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/59000000/58060000/58053600/58053504/a63b7f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/59000000/58060000/58053600/58053504/525a4b92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/59000000/58060000/58053600/58053504/55f795d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/59000000/58060000/58053600/58053504/0763edc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Yurt at Stillhouse Farm \*Wifi \*Creek \*Private \*Less than 5 miles from VMI + W&L

Lexington

10/10

Exceptional

(52)

"Beautiful, peaceful, thoughtfully decorated and stocked. Our family (Dad, Mom, 10 year old daughter and 8 year old daughter) spent one magical night here on our trip to see caverns and the safari. The river, creek, rolling green land, and wildlife are the perfect setting, and the yurt is so comfortable. The bedding is luxurious!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Paige W.

CA $238

CA $400 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Lexington-Hotels-Yurt-At-Stillhouse-Farm-Wifi-Creek-Private-Less-Than-5-Miles-From-VMI-WL.h58053504.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95250000/95249100/95249013/a0b85052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/96000000/95250000/95249100/95249013/37b34397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/96000000/95250000/95249100/95249013/76c2747a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95250000/95249100/95249013/4ba1cd32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### MidMountain Retreat, a budding arts space in a historic home on the James River

Natural Bridge Station

8.0/10

Very good

(4)

"This place has potential, but there are several things that need to be done for the property to bring it up to the standard of a vacation rental. First and foremost, it needs a deep cleaning. We spent our first full day of vacation cleaning the kitchen and bathrooms. The beds are awful. Awful. The appliances are in need of replacement. The entire home needs somebody with resources to invest some cash and bring it to a standard worthy of charging people to stay. Some other things of note,...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael M.

CA $151

CA $476 total

includes taxes & fees

Nov 3 - Nov 4

[](https://www.expedia.ca/MidMountain-Retreat.h95249013.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/96000000/95790000/95780200/95780104/f7f913f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/96000000/95790000/95780200/95780104/c8a6e127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95790000/95780200/95780104/d1870f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95790000/95780200/95780104/e6c77912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin Retreat at Stillhouse Farm NEW

Lexington

10/10

Exceptional

(25)

"Would definitely stay here again. The house was clean, everything we needed and the location was perfect: close to Lexington, beautiful mountain views, awesome birding - saw several warblers including an Indigo Bunting"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kathy S.

CA $276

CA $450 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Lexington-Hotels-Cabin-Retreat-At-Stillhouse-Farm-NEW.h95780104.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111030000/111028100/111028018/23b235d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111030000/111028100/111028018/c98b7863.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111030000/111028100/111028018/2dcfb70e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111030000/111028100/111028018/3d7d54d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Osceola Mill is a boutique inn located in the Shenandoah Valley 20 minutes from Lexington and Staunton.

Vesuvius

10/10

Exceptional

(1)

"Booked this property for 3 nights as we were attending a VMI graduation and a wedding. This was perfect. Linda made our stay awesome. We did a red-eye in and were able to check in early for a quick nap. The breakfast every morning was sooooo good. She even arranged a tea tasting, which unfortunately we were not able to attend because of our conflicting schedule. The room was large and comfortable. They use StarLink WiFi so no problems with connectivity. Linda's attitude made the visit in...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Dee N.

CA $239

CA $310 total

includes taxes & fees

Nov 4 - Nov 5

[](https://www.expedia.ca/Raphine-Hotels-Osceola-Mill-Is-A-BB-Inn-Located-In-The-Shenandoah-Valley-20-Minutes-From-Lexington-And-Staunton.h111028018.Hotel-Information)

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.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-14&endDate=2025-11-15&regionId=950881170208768000&adults=2&sort=RECOMMENDED&openPlayBack=true)

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## Top The Chessie Trail Hotel Reviews

## Find out more about The Chessie Trail

**Everything you need to know about** **The Chessie Trail** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the The Chessie Trail vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

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Whenever you want to travel, a warm welcome awaits you in The Chessie Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A The Chessie Trail vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of The Chessie Trail vacation rentals we have selected for you start as low as CA $265 per night. Entering your travel dates in the search wizard you might find even better deals!

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![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFVElEQVR4Xu3bMXLjOBBGYbgUKJwj8Cg+GnQ0HUVHmNCBSlj/jSYapGhPdTBbNdZ7iagmiE8Zhq7d0v6Hyn7wNwJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIqgm5l12LRrXfvJazPm6a1/a7L/gc+dIxivxBBWKBzIGsoxGIBTIHso5GPxWp8a0J+ezyuf5NyGeOlPKrL/noo5Ouf2vVaLsXiAUSgVggIA0ExG/Mp/ei6YxMrTv6Vz0YqxaQPh+BgCgQkAICsi6KywNkHhUd6E/5T2kgICAg66K4BOkXICBJpOmMt/fpq0bjfbq1Rynv/Wp+xQYBAWkgICAgeSSakEd/tkxI27uGjEBAGogFUuMbSA8EpO2RbUtfa4/bjt+PdtXYGeRgtKvGziAHo101dgY5GO2qsTPIwWhXjZ1BDka7auwMcjDaVWPnCfm6h96nP/oZb4874sWx/0UgIF8HsgYC8nUgaz8XmR+307uU+Au376i37ui2GdlPsX8v1FgCEoGANBAQEJAZ8RtxoG/XzqN4nxZS+ujNF/qvGw+CgICAgPhCEAWiSVzetTpOb1+r0eoqO9AtH/kq/3+gznrQqrEzSAHRLZACAtKrsTNIeXnkON/RmsaPMbrJ/T4QkONA5kBAjgOZ+5HIvZ/LD53eutNP7/nl2VepONCXPve37rOub7qq8QwICEifg4CAbFaBeJf+Pj2vnV+xNTr1Y39FVLhtXQUC0kBALBCQBvJHREf1utYbZ7w9bjvuR9FVT4D4SB8gcyA9kP2OIHMgvVdC7mPj9+nxS/ED3VrWxeuxr04afOUqEBAQEBCQSwGJtkht8Ydq7Wiu/ydf9vht2nHrbhHbawQCAtJvg4Cse41AQLxHf3a9cSnxR+9D11fZvwRsNNwRiAUCAtIDmQOxXhq5T2e8dxqPX/vAEK2yHfV839FX+ciq/lWTuATRh6/ykVX9qyZxCaIPX+Ujq/pXTeISRB++ykdW9a+axCWIPnyVj6zqXzWJSxB9+CofWdW/ahKXIPrwVT6yqn/VJC7vumWnt+3Y2q2vtjP+3RavO86rrEvxn3Lu3+2njEBilQUCYoFoMUhcgvTRKyI1vjVt4We8de6IrzL3Q/NFix0Zb90gIA0EZH8DBARkNCFNa+NAb+0mpPX36asQddfGvsp2vGlQ+01DvDECAbFAQBoICMjahNz7jcdYtvR5/NF7LPXRp6tV9mD8FF+svTwQCwQEBMQXay8PxHpppOmMtzfla9/RzvjtsT9WPbX9x0EB2ax6CgQEBKQH8tTLIU9H9RL31uxx39HS8O7XY2S/bgoEBAQExEcg3q3vA3KYP/6m64+xi35K8QNdP8V+nXUda8bIFsXlQSB91QikgDwH0leNQArIc/8o4jtGi6aXMiM28q4atHbTh9w3EBAbjUAayLTCWjS9FJBYCdJANjfm09vep8991IZrL+IqHjwYKRAQEBAFshspEBC7YS/PY8cYvdviNf+fi2PHkY2++Qs3CAgICMgcSAN5RpoOdN+x9Pfp037kD1o28nykQGIEAgICAgLyJ8Qff/gZL8Qej1WTO7+Ih6tAQEBAQPYPeiAg2xu2tunx+HN233qzauu+r6PTZglIBGKB2AgEpIHMvTCybenz7eOWvWL7f/Jl1Wb/Eij6KcMdgVggc0ufg/Q1CsQCmVv6HKSvUT8S+XuBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJNXPQf4D0dfBcqro4SEAAAAASUVORK5CYII=)