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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middlebrook condo rentals

Interior

1. 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, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$188 nightly
The price is $211
Sep 20 - Sep 21
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A mountainous landscape with dense green forests and a clear sky.

2. 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, (333 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
$205 nightly
The price is $230
Sep 23 - Sep 24
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds

3. 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
$220 nightly
The price is $247
Sep 20 - Sep 21
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Dining

4. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (35 reviews)
"Great stay for my family!"
United States
Joel M.
$225 nightly
The price is $253
Sep 20 - Sep 21
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
Terrace/patio

5. 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 21 - Sep 22
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Outdoor dining

6. 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, (129 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
$230 nightly
The price is $258
Sep 20 - Sep 21
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
Property grounds

7. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (48 reviews)
"Wonderful stay, wonderful place!! The view, the fireplace, well appointed, comfortable bed, comfortable furniture, very clean...will definitely stay again! Thank you!!"
United States
Art P.
$274 nightly
The price is $308
Sep 30 - Oct 1
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Coffee/tea maker, fridge, microwave, oven

8. 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.
$288 nightly
The price is $323
Sep 20 - Sep 21
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Exterior

9. 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, (122 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$254 nightly
The price is $285
Sep 22 - Sep 23
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Fireplace

10. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
$174 nightly
The price is $196
Sep 29 - Sep 30
Total with taxes and fees
Where the Trail Ends
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.
$282 nightly
The price is $286
Sep 20 - Sep 21
Total with taxes and fees
Mountain Retreat in Wintergreen!
Smart TV, fireplace, books

12. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails

Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this beautiful condo at Wintergreen and couldn’t be happier with our experience. The condo was exceptionally clean, comfortable, and well equipped with everything we needed for a relaxing weekend.The view overlooking the 18th hole was gorgeous, and we loved being able to sit and enjoy the scenery. The condo itself was cozy and inviting, and it was clear that the owners had put a lot of thought into making it a comfortable place to stay.We would absolutely stay here...
United States
Op V.
$280 nightly
The price is $314
Oct 12 - Oct 13
Total with taxes and fees
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Terrace/patio

13. 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
Oct 12 - Oct 13
Total with taxes and fees
Cozy Lux Condo at Wintergreen Resort
Coffee/tea maker, fridge, microwave, oven

14. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Wintergreen Resort
10.0 out of 10, Exceptional, (42 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$275 nightly
The price is $308
Sep 20 - Sep 21
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
Condo, Private Bathroom (Mountain Vista View) | Lounge

15. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
$229 nightly
The price is $257
Sep 30 - Oct 1
Total with taxes and fees
Mountain View Vista
1 bedroom, iron/ironing board, WiFi (free), bed sheets

16. 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, (17 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
$235 nightly
The price is $264
Sep 29 - Sep 30
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Coffee/tea maker, fridge, microwave, oven

17. 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.
$290 nightly
The price is $326
Oct 12 - Oct 13
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Exterior

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

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
$272 nightly
The price is $305
Sep 21 - Sep 22
Total with taxes and fees
Pet-Friendly Retreat Walk to Slopes & Village!
Exterior

19. 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.
$238 nightly
The price is $267
Sep 20 - Sep 21
Total with taxes and fees
Timbers Studio 46 with Wintergreen Advantage
Outdoor pool, a heated pool

20. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
United States
Shannon T.
$296 nightly
The price is $332
Sep 20 - Sep 21
Total with taxes and fees
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
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 Staunton

Sleep Inn Staunton

10/10 Excellent
"Clean room and very good staff"
Inayat 1-night trip
Posted 4 hours ago
Sleep Inn Staunton

Find out more about Middlebrook

Middlebrook Condo Rentals information

Number of reviews
689
Accommodation
341 Condo Rentals
Lowest Price
$196
Highest Price
$332

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