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Our top choices for Middlebrook condo rentals

Interior
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Condo in Wintergreen Resort

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
2.0 star property
10.0 out of 10, Exceptional, (2)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
$243 nightly
The price is $273
Jan 12 - Jan 13, 2026
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Property grounds
The Modern Mountain Condo

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (36)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
$247 nightly
The price is $278
Jan 13 - Jan 14, 2026
Total with taxes and fees
The Modern Mountain Condo
Interior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Condo in Wintergreen Resort

Wintergreen. Sunset Vista Villa - Close to the ski slopes
10.0 out of 10, Exceptional, (94)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
$290 nightly
The price is $325
Jan 12 - Jan 13, 2026
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Condo in Wintergreen Resort

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
2.0 star property
10.0 out of 10, Exceptional, (25)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
$330 nightly
The price is $371
Jan 13 - Jan 14, 2026
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Pool
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Condo in Roseland

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
$237 nightly
The price is $266
Jan 5 - Jan 6, 2026
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Interior
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Condo in Roseland

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
9.8 out of 10, Exceptional, (22)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
$224 nightly
The price is $252
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Condo in Roseland

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (304)
"Great view!!"
United States
Suzanne W.
$216 nightly
The price is $242
Jan 4 - Jan 5, 2026
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
TV, fireplace
Mountain View Vista: Resort Condo w/ Views

Condo in Wintergreen Resort

Mountain View Vista: Resort Condo w/ Views
9.4 out of 10, Exceptional, (8)
"Beautiful view!"
United States
Serge L.
$269 nightly
The price is $302
Jan 13 - Jan 14, 2026
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
Microwave, oven, stovetop, dishwasher
Overlook 180 degree views w/Peloton!

Condo in Wintergreen Resort

Overlook 180 degree views w/Peloton!
9.4 out of 10, Exceptional, (3)
"Excellent stay. Thank you!"
United States
Kimberly B.
$329 nightly
The price is $377
Jan 13 - Jan 14, 2026
Total with taxes and fees
Overlook 180 degree views w/Peloton!
Property grounds
You deserve it all! Awesome Views, Comfy Condo & Elevator!

Condo in Chestnut Springs

You deserve it all! Awesome Views, Comfy Condo & Elevator!
9.8 out of 10, Exceptional, (196)
"Nice view along with a spacious layout. Was very nice location. "
United States
Daniel
$359 nightly
The price is $403
Dec 30 - Dec 31
Total with taxes and fees
You deserve it all! Awesome Views, Comfy Condo & Elevator!
TV, fireplace
Panoramic Peak: Wintergreen Condo with Views

Condo in Wintergreen Resort

Panoramic Peak: Wintergreen Condo with Views
9.6 out of 10, Exceptional, (32)
"Very clean, well organized, excellent views"
United States
Guy M.
$307 nightly
The price is $345
Jan 13 - Jan 14, 2026
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Outdoor pool
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Condo in Wintergreen Resort

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
10.0 out of 10, Exceptional, (39)
"Cute and cozy. Perfect for our weekend away in the mountains. Close to golf, hiking trails and restaurants in Wintergreen. The bed was very comfortable and the kitchen was well stocked. Ritta was very responsive and communicative. We loved that we could bring our pup with us!"
United States
Carol K.
$269 nightly
The price is $302
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Terrace/patio
New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂

Condo in Wintergreen Resort

New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂
9.6 out of 10, Exceptional, (10)
"Great location, communicative host! I would definitely stay here again!"
United States
Jaime B.
$740 nightly
The price is $831
Jan 5 - Jan 6, 2026
Total with taxes and fees
New Listing!100 FT FROM THE SLOPES! 4bd/3bth Ski In/Out Dobie Condo + Loft ❄⛄⛷🏂
A heated pool
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Condo in Wintergreen Resort

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
9.8 out of 10, Exceptional, (138)
"Perfect location right across from the village. Very comfortable and clean. "
United States
Erin F.
$395 nightly
The price is $444
Jan 4 - Jan 5, 2026
Total with taxes and fees
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Property grounds
Endless Mountain Top Views from All The Way Up!

Condo in Wintergreen Resort

Endless Mountain Top Views from All The Way Up!
10.0 out of 10, Exceptional, (91)
"Perfect location for our weekend stay! Close to trails and breweries and gorgeous views. Responsive hosts, clean and cozy condo. "
United States
Cari B.
$373 nightly
The price is $418
Dec 28 - Dec 29
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
Fireplace
Firefly on The Ridge: Mountain + Ski Slope Views

Condo in Wintergreen Resort

Firefly on The Ridge: Mountain + Ski Slope Views
2.0 star property
$361 nightly
The price is $389
Jan 13 - Jan 14, 2026
Total with taxes and fees
Firefly on The Ridge: Mountain + Ski Slope Views
Fridge, microwave, oven, stovetop
NEW! Your Ski-In/Ski-Out Wintergreen Escape

Condo in Wintergreen Resort

NEW! Your Ski-In/Ski-Out Wintergreen Escape
2.0 star property
$593 nightly
The price is $654
Jan 7 - Jan 8, 2026
Total with taxes and fees
NEW! Your Ski-In/Ski-Out Wintergreen Escape
Property grounds
The Fairway Chalet / 2 BR + Loft

Condo in Wintergreen Resort

The Fairway Chalet / 2 BR + Loft
2.0 star property
$279 nightly
The price is $313
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Fairway Chalet / 2 BR + Loft
Fridge, microwave, oven, stovetop
Steps from WLU & VMI Loft with Private Parking

Condo in Lexington

Steps from WLU & VMI Loft with Private Parking
9.6 out of 10, Exceptional, (10)
"We loved everything about our stay! The location is excellent, amenities outstanding, and check-in/check out was super smooth! The location makes it easy to walk around town for all the great shops and restaurants. We would absolutely stay again!!"
United States
Rory D.
$404 nightly
The price is $458
Jan 21 - Jan 22, 2026
Total with taxes and fees
Steps from WLU & VMI Loft with Private Parking
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.
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Top Middlebrook Hotel Reviews

Tru By Hilton Staunton

Tru By Hilton Staunton

10/10 Excellent
"Tru is always been a great place to stay Breakfast is great Rooms are always neat and clean Only issue was limited hot water but that could have been due to the fact the hotel was sold out and packed with guests Didn’t bother me at all"
Gayle 1-night trip
Posted 4 days ago
Tru By Hilton Staunton

Find out more about Middlebrook

Middlebrook Condo Rentals information

Number of reviews
1,116
Accommodation
298 Condo Rentals
Lowest Price
$242
Highest Price
$831

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