Photo by Brittany Davidson

Search Chalets in Middlebrook from CA $501

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Middlebrook chalets

A hot tub with a wooden deck and a scenic view of mountains and trees.

1. Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views

Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views
Vesuvius
10.0 out of 10, Exceptional, (22 reviews)
"Excellent location and views. Beautiful grounds. The house is nicely decorated. It sleeps 6 adults and 4 children. If there was more attention given to the maintenance of mechanical things in the house we would definitely have given this a five star review."
United States
David K.
The price is CA $502
CA $926 total
includes taxes & fees
Nov 12 - Nov 13
Luxury Mountain Lodge: Hot Tub and Incredible Mountain Views
A cabin with a deck, surrounded by dense forest.

2. Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16

Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
Deer Springs
10.0 out of 10, Exceptional, (11 reviews)
"It's a nice house, and check in/out was super easy."
United States
Chris R.
The price is CA $509
CA $1,183 total
includes taxes & fees
Nov 8 - Nov 9
Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16
A large, two-story house with multiple decks and a spacious front porch, surrounded by dense forest.

3. Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23
Chestnut Springs
9.8 out of 10, Exceptional, (17 reviews)
"Excellent amenities and host was attentive. Great place to stay with a large group. "
United States
Karen N.
The price is CA $957
CA $1,999 total
includes taxes & fees
Nov 16 - Nov 17
Fully Loaded 8BR in Wintergreen! Sleeps 23
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

Learn more about Middlebrook

Nestled in Virginia's scenic countryside, this charming village offers easy access to the fascinating Frontier Culture Museum and captivating performances at the American Shakespeare Centre. History buffs can explore The Woodrow Wilson Presidential Library nearby, while outdoor enthusiasts will appreciate the natural splendour of George Washington National Forest and Sherando Lake Recreation Area.

See all hotels in Middlebrook
A snow-covered road winding through a forest with bare trees.
Photo by Brittany Davidson
Open Photo by Brittany Davidson

Top reviews in Middlebrook

A multi-story hotel with a covered entrance, parking lot, and a clear sky.
Holiday Inn Express & Suites Staunton by IHG

Holiday Inn Express & Suites Staunton by IHG

Holiday Inn Express & Suites Staunton by IHG
Staunton

10/10 Excellent

Très propre, lit confortable et personnel très gentil
Canada
Marie-Michele
Reviewed August 10, 2026
Holiday Inn Express & Suites Staunton by IHG

Explore a world of travel with Expedia