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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 305 Condo Rentals in Middlebrook with updated reviews, rates, and availability.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (270)
"We really appreciate the cleanliness and location of this property! We had a great stay and look forward to returning! Ps love the art!! "
The price is $241
includes taxes & fees
$215 per night
May 5 - May 6
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (312)
"Love this condo! Has a fireplace, upstairs and view of the falling snow!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (124)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is $246
includes taxes & fees
$219 per night
May 4 - May 5
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Interior

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (62)
"The property was well maintained with exceptional views. We enjoyed our stay from start to finish and never grew tired of the property or the mountain views."
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Wintergreen Condo -Steps to Ski and restaurants
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

9.8 out of 10, Exceptional, (16)
"Excellent location."
The price is $266
includes taxes & fees
$237 per night
May 6 - May 7
Wintergreen Condo -Steps to Ski and restaurants
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Property grounds

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10.0 out of 10, Exceptional, (170)
"We had another great stay at this property and already rebooked for next year!"
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Smart TV, fireplace, books

Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo

10.0 out of 10, Exceptional, (4)
"We have stayed here several times and love it! Great updated property and with fully equipped kitchen. The owners are very easy to work with, and the location is perfect for ski in/ski out with minimal stairs. "
Premiere Two bedroom getaway Slope Side Wintergreen Resort Condo
Endless Mountain Top Views from All The Way Up!
Property grounds

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (70)
"The property was great and exactly as advertised. I’ve stayed at four places around Wintergreen, and this was definitely the best. The communication and responsiveness from the hosts was perfect."
The price is $317
includes taxes & fees
$282 per night
May 4 - May 5
Endless Mountain Top Views from All The Way Up!
View from the Top
Property grounds

View from the Top

10.0 out of 10, Exceptional, (54)
"Great quick stay in a lovely area with an amazing view"
View from the Top
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (68)
"Great location and property"
The price is $279
includes taxes & fees
$248 per night
May 5 - May 6
Wintergreen. Sunset Vista Villa - Sea of Mountains
Downtown Loft - King Beds - Walk to WLU & VMI!
Fridge, microwave, oven, stovetop

Downtown Loft - King Beds - Walk to WLU & VMI!

9.6 out of 10, Exceptional, (8)
"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!!"
The price is $475
includes taxes & fees
$440 per night
May 12 - May 13
Downtown Loft - King Beds - Walk to WLU & VMI!
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Outdoor dining

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

9.6 out of 10, Exceptional, (26)
"Great place to stay, would book again!"
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Walk to Market/Private community outdoor pool!
Fridge, microwave, oven, stovetop

Walk to Market/Private community outdoor pool!

9.6 out of 10, Exceptional, (67)
"Nice condo, near all the Wintergreen activities."
Walk to Market/Private community outdoor pool!
Walk to Lifts: Wintergreen Resort Condo
Exterior

Walk to Lifts: Wintergreen Resort Condo

7.6 out of 10, Good, (5)
"Everything was clean, everything we needed for our stay! Was to slopes, walk to the market, close to everything! We love laurelwoods! "
Walk to Lifts: Wintergreen Resort Condo
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Miscellaneous

Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views

9.8 out of 10, Exceptional, (46)
"Great family getaway. While it rained and conditions were terrible for snowboarding/skiing, we had everything we needed to be comfortable while staying at this condo! "
Top of Mountain 2 BR Condo, Short Walk to Highlands Ski Lift and Scenic Views
Wintergreen Resort Vacation Rental w/ Pool Access!
Property grounds

Wintergreen Resort Vacation Rental w/ Pool Access!

10.0 out of 10, Exceptional, (16)
"Really worked well for our family "
Wintergreen Resort Vacation Rental w/ Pool Access!
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Property grounds

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

10.0 out of 10, Exceptional, (141)
"This was our second stay here. Perfect for a couple! Great location in the mountain right near the general store and main lodge. "
Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.
Vineyards, Views & Brews with 2 Floors
TV, fireplace, books

Vineyards, Views & Brews with 2 Floors

10.0 out of 10, Exceptional, (65)
"We loved the condo .I've stayed in many different condo complexes at Wintergreen (i've also owned a couple) and this is definitely near the top of my list along with being on top of the mountain.Beautiful view!!"
The price is $399
includes taxes & fees
$357 per night
May 5 - May 6
Vineyards, Views & Brews with 2 Floors
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Miscellaneous

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

9.4 out of 10, Exceptional, (10)
"I was at a conference at Wintergreen and this was the perfect location. The area is beautiful! The condo was clean and well-equipped. "
The price is $220
includes taxes & fees
$196 per night
May 6 - May 7
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Ski-In Ski-Out Wintergreen Condo w/ Balcony
Interior

Ski-In Ski-Out Wintergreen Condo w/ Balcony

9.6 out of 10, Exceptional, (42)
"Condo was perfect for our mommy/ teen(14) daughter getaway. Location was awesome and super convenient for ski in/ski out, walking to the market, restaurants and Mountain inn for Starbucks!!(for my teen). Condo was adequately equipped and stocked with basic necessities(coffee and basic cooking spices)If you have little kids taking ski lessons from ski school you can watch them right off the balcony. We met Ken, Property Manager when we arrived and he made us feel welcome. Skiing conditions...
Ski-In Ski-Out Wintergreen Condo w/ Balcony
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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Other property types in Middlebrook

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (270)
"We really appreciate the cleanliness and location of this property! We had a great stay and look forward to returning! Ps love the art!! "
The price is $241
includes taxes & fees
$215 per night
May 5 - May 6
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Valley Extended Suites
Studio Suite | Private kitchen | Full-size fridge, microwave, oven, stovetop

Valley Extended Suites

3.0 star property
9.0 out of 10, Wonderful, (179)
"Great place!! Very impressed!! If I’m in the area again, will definitely stay"
The price is $120
includes taxes & fees
$107 per night
Jun 1 - Jun 2
Valley Extended Suites
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (124)
"This property is one of the best prperties we have ever stayed at. The owner is very responsive and goes the extra mile. We will definitely rent this property again!!"
The price is $246
includes taxes & fees
$219 per night
May 4 - May 5
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
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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