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Our top choices for Middlebrook condo rentals
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodgeWintergreen Resort
10.0 out of 10, Exceptional, (2)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
Lloyd F.
$220 nightly
The price is $247
Jan 27 - Jan 28, 2026
Total with taxes and fees
The Modern Mountain Condo
The Modern Mountain CondoWintergreen Resort
10.0 out of 10, Exceptional, (36)
"Quiet, one-night stay while in the area for an event. "
Julie M.
$247 nightly
The price is $278
Jan 13 - Jan 14, 2026
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen. Sunset Vista Villa - Close to the ski slopesWintergreen Resort
10.0 out of 10, Exceptional, (94)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
Amanda W.
$282 nightly
The price is $316
Jan 19 - Jan 20, 2026
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Retreat @ 3 Ridges / 3 min walk -> Slopes & DiningWintergreen Resort
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. "
Cassie H.
$330 nightly
The price is $371
Jan 13 - Jan 14, 2026
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendlyRoseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
Pete K.
$237 nightly
The price is $266
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf CourseRoseland
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"
Phil P.
$224 nightly
The price is $252
Jan 5 - Jan 6, 2026
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.Roseland
9.0 out of 10, Wonderful, (304)
"Great view!!"
Suzanne W.
$216 nightly
The price is $242
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
Mountain View Vista: Resort Condo w/ ViewsWintergreen Resort
9.4 out of 10, Exceptional, (8)
"Beautiful view!"
Serge L.
$269 nightly
The price is $302
Jan 13 - Jan 14, 2026
Total with taxes and fees
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
10/10 Excellent
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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