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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 lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
$193 nightly
The price is $217
May 13 - May 14
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
$201 nightly
The price is $226
May 13 - May 14
Total with taxes and fees
Mountain Inn Studio 96 with Wintergreen Advantage

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (13 reviews)
"Beautiful condo"
United States
Mary C.
$259 nightly
The price is $291
May 13 - May 14
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views

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-friendly
Roseland
9.6 out of 10, Exceptional, (153 reviews)
"Very clean and pet-friendly "
United States
Heston
$221 nightly
The price is $248
May 19 - May 20
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
$367 nightly
The price is $406
May 17 - May 18
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
$239 nightly
The price is $268
May 18 - May 19
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
$267 nightly
The price is $300
May 13 - May 14
Total with taxes and fees
Three Ridges 64 With Wintergreen Advantage

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (111 reviews)
"Great and comfortable place to stay! Host was very welcoming and responsive. "
United States
Jon L.
$290 nightly
The price is $325
May 13 - May 14
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
$206 nightly
The price is $232
May 17 - May 18
Total with taxes and fees
Where the Trail Ends

Renovated Wintergreen Condo with Pool Access, and more!

Renovated Wintergreen Condo with Pool Access, and more!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
$294 nightly
The price is $298
May 13 - May 14
Total with taxes and fees
Renovated Wintergreen Condo with Pool Access, and more!

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
United States
Sarah L.
$263 nightly
The price is $295
May 18 - May 19
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (44 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
$262 nightly
The price is $294
May 18 - May 19
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
$279 nightly
The price is $313
May 18 - May 19
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"Great location and cozy condo! "
United States
Molly M.
$238 nightly
The price is $267
May 13 - May 14
Total with taxes and fees
Diamond Hill Studio 09 with Wintergreen Advantage

NEW! Your Ski-In/Ski-Out Wintergreen Escape

NEW! Your Ski-In/Ski-Out Wintergreen Escape
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place!"
United States
Chris C.
$301 nightly
The price is $338
May 18 - May 19
Total with taxes and fees
NEW! Your Ski-In/Ski-Out Wintergreen Escape

Mountain Inn Lodge 54 with Wintergreen Advantage

Mountain Inn Lodge 54 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"We were in the area looking to possibly relocate and this loft on the mountain was a beautiful stay. Convenient to restaurants within walking distance. We would definitely book again!"
United States
Erin C.
$223 nightly
The price is $250
May 14 - May 15
Total with taxes and fees
Mountain Inn Lodge 54 with Wintergreen Advantage

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, (320 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$216 nightly
The price is $242
May 20 - May 21
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Stoneridge Woods 05 with Wintergreen Advantage

Stoneridge Woods 05 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Loved the house. The layout was great and worked great for our family."
United States
Torry M.
$334 nightly
The price is $375
May 13 - May 14
Total with taxes and fees
Stoneridge Woods 05 with Wintergreen Advantage

Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (31 reviews)
"Amazing place with even more amazing views. Very comfortable and beautiful place. We had high expectations based on the pictures in the listing, and the place exceeded these high expectations. Fantastic place."
United States
missy s.
$278 nightly
The price is $312
May 13 - May 14
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!

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 Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$220 nightly
The price is $247
May 17 - May 18
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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

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Middlebrook Condo Rentals information

Number of reviews
825
Accommodation
312 Condo Rentals
Lowest Price
$217
Highest Price
$406

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