A snow-covered road winding through a forest with bare trees.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middlebrook condo rentals

A mountainous landscape with dense green forests and a clear sky.

1. 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, (330 reviews)
"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."
United States
Virginia
$243 nightly
The price is $273
Sep 17 - Sep 18
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds

2. 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, (159 reviews)
"We had a calm and relaxing mountain get a way. The property was charming and perfect for us, clean and organized. The location was great. We loved to go for walks nearby and visit the gnomes and fairies in the trees. We would love to make it an annual trip and would definitely stay here again."
United States
Michelle
$223 nightly
The price is $250
Aug 19 - Aug 20
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Interior

3. 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, (34 reviews)
"Everything was perfect! "
United States
Danielle B.
$190 nightly
The price is $213
Aug 19 - Aug 20
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Outdoor dining

4. Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (128 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$230 nightly
The price is $258
Aug 19 - Aug 20
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
Exterior

5. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Wintergreen Resort
10.0 out of 10, Exceptional, (121 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$243 nightly
The price is $272
Aug 19 - Aug 20
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Property grounds

6. Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (118 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
$231 nightly
The price is $260
Aug 19 - Aug 20
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
Terrace/patio

7. Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (5 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
$286 nightly
The price is $290
Aug 19 - Aug 20
Total with taxes and fees
Cozy Lux Condo at Wintergreen Resort
Terrace/patio

8. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay for our family of 4 for a wedding weekend. Easy check-in and close to the Inn."
United States
Scott M.
$236 nightly
The price is $265
Sep 9 - Sep 10
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Fireplace

9. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Wonderful location. Wonderful host. We will be back!"
United States
April S.
$175 nightly
The price is $197
Aug 31 - Sep 1
Total with taxes and fees
Where the Trail Ends
Coffee/tea maker, fridge, microwave, oven

10. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (42 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
Aug 19 - Aug 20
Total with taxes and fees
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Exterior

11. Mountain Retreat in Wintergreen!

Mountain Retreat in Wintergreen!
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.
$286 nightly
The price is $290
Aug 19 - Aug 20
Total with taxes and fees
Mountain Retreat in Wintergreen!
Coffee/tea maker, fridge, microwave, oven

12. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (15 reviews)
"The condo was beautiful and clean and worked perfectly for our group."
United States
Eric W.
$292 nightly
The price is $328
Aug 19 - Aug 20
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Condo, Private Bathroom (Mountain Vista View) | Lounge

13. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
$229 nightly
The price is $257
Aug 20 - Aug 21
Total with taxes and fees
Mountain View Vista
Property grounds

14. Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very clean and nicely supplied and decorated. Wonderful views from the living room! Planning on going back to this property again. "
United States
Charlie B.
$281 nightly
The price is $316
Aug 24 - Aug 25
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
Coffee/tea maker, fridge, microwave, oven

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

Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Pet-friendly, very hospitable, had coffee and Brita filter for water, linens, paper towels, everything we needed. "
United States
Sarah L.
$264 nightly
The price is $296
Sep 8 - Sep 9
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Exterior

16. Northridge 07 With Wintergreen Advantage

Northridge 07 With Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Good Stay! Clean, need to have a lock on master bathroom. Door slides"
United States
William M.
$302 nightly
The price is $339
Aug 19 - Aug 20
Total with taxes and fees
Northridge 07 With Wintergreen Advantage
Exterior

17. Pet-Friendly Retreat Walk to Slopes & Village!

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
$262 nightly
The price is $294
Sep 8 - Sep 9
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
Coffee/tea maker, fridge, microwave, oven

18. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"We had an incredible stay this past week. The condo "
United States
Holly M.
$372 nightly
The price is $411
Aug 19 - Aug 20
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Exterior

19. Mountain Inn Lodge 55 with Wintergreen Advantage

Mountain Inn Lodge 55 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"The condo is located very close to the ski slopes and several restaurants. Good for a short weekend stay!"
United States
Sarah H.
$265 nightly
The price is $297
Aug 19 - Aug 20
Total with taxes and fees
Mountain Inn Lodge 55 with Wintergreen Advantage
Exterior

20. Timbers Studio 46 with Wintergreen Advantage

Timbers Studio 46 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...
United States
Madison D.
$241 nightly
The price is $270
Aug 19 - Aug 20
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
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

Sleep Inn & Suites Virginia Horse Center

Sleep Inn & Suites Virginia Horse Center

8/10 Good
"Stayed on our way thru to go to the Safari Park, convenient location, very good staff nice and helpful. Good breakfast, comfortable beds. Only complaints would be our room seemed to not be cleaned before we arrived, it had dirty towels in the bathroom, and the tub was not clean at all. Also the smell of chlorine was unbearable to be able to stay in the pool area, it burned our little one’s eyes."
Robert 1-night trip
Posted 1 hour ago
Sleep Inn & Suites Virginia Horse Center

Find out more about Middlebrook

Middlebrook Condo Rentals information

Number of reviews
Accommodation
341 Condo Rentals
Lowest Price
$257
Highest Price
$343

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