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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlebrook condo rentals

A wooden deck with a round table and chairs, overlooking a grassy area with trees.

1. 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.
$229 nightly
The price is $257
Oct 4 - Oct 5
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
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
$216 nightly
The price is $242
Oct 6 - Oct 7
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

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, (36 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$199 nightly
The price is $223
Oct 7 - Oct 8
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
A garden with a variety of flowers and trees at dusk.

4. 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, (161 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
$220 nightly
The price is $247
Nov 1 - Nov 2
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

5. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (37 reviews)
"Great stay for my family!"
United States
Joel M.
$227 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
Updated! Cozy and clean two bedroom condo.
A two-story house with a stone foundation, a large front porch, and a chimney.

6. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (124 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
$246 nightly
The price is $276
Oct 5 - Oct 6
Total with taxes and fees
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

7. 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.
$285 nightly
The price is $289
Oct 4 - Oct 5
Total with taxes and fees
Mountain Retreat in Wintergreen!
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

8. 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.
$261 nightly
The price is $293
Nov 2 - Nov 3
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a granite countertop.

9. 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.
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

10. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (38 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.
$249 nightly
The price is $280
Oct 4 - Oct 5
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Views from the porch are beautiful!Essentials ar all there Well thought out for a rentalHope to be back for another anniversary"
United States
rodney f.
$280 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Luxury Condo in the Sky! Finest in Wintergreen!
Private kitchen

12. "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, (44 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
$278 nightly
The price is $312
Oct 4 - Oct 5
Total with taxes and fees
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A two-story wooden cabin with a wooden deck and a small porch.

13. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Enjoyed our stay."
United States
Alice W.
$227 nightly
The price is $255
Oct 4 - Oct 5
Total with taxes and fees
Walk to Market/Private community outdoor pool!
A living room with a grey sofa, a marble coffee table, a fireplace, and a TV mounted on the wall.

14. Newly Renovated Condo at Ski Wintergreen Resort

Newly Renovated Condo at Ski Wintergreen Resort
Wintergreen Resort
$298 nightly
The price is $335
Oct 12 - Oct 13
Total with taxes and fees
Newly Renovated Condo at Ski Wintergreen Resort
A dining area with a wooden table, chairs, and a view of the kitchen.

15. 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, (6 reviews)
$315 nightly
The price is $353
Oct 12 - Oct 13
Total with taxes and fees
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

16. Mountain View Vista

Mountain View Vista
2.0 star property
Nellysford
$229 nightly
The price is $257
Oct 12 - Oct 13
Total with taxes and fees
Mountain View Vista
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

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.
$275 nightly
The price is $309
Oct 5 - Oct 6
Total with taxes and fees
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
A house with a covered porch, two Adirondack chairs, and a welcome mat.

18. 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
A wooden deck with two Adirondack chairs facing a scenic view of a sunset over a mountainous landscape.

19. 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, (121 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
$293 nightly
The price is $329
Oct 4 - Oct 5
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!
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

8/10 Good
"Clean and quiet"
Duane 1-night trip
Posted 10 hours ago
Sleep Inn Staunton

Find out more about Middlebrook

Middlebrook Condo Rentals information

Number of reviews
996
Accommodation
341 Condo Rentals
Lowest Price
$223
Highest Price
$353

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