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Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Middlebrook condo rentals

Property grounds

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, (108 reviews)
"Nice place!"
United States
Gregory G.
The price is CA $106
CA $337 total
includes taxes & fees
Jun 21 - Jun 22
Endless Mountain Top Views from All The Way Up!
1 bedroom, desk, internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (45 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is CA $196
CA $416 total
includes taxes & fees
Jun 21 - Jun 22
Panoramic Peak: Wintergreen Condo with Views
Property grounds

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, (155 reviews)
"Lisa we are happy for staying at your places it awesome and we had great time, thank you let us use your home"
United States
Issac S.
The price is CA $155
CA $351 total
includes taxes & fees
Jul 6 - Jul 7
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (116 reviews)
"Great location"
United States
Chrissy R.
The price is CA $178
CA $392 total
includes taxes & fees
Jun 24 - Jun 25
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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, (324 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $164
CA $383 total
includes taxes & fees
Jun 25 - Jun 26
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Fireplace

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (53 reviews)
"Very good host, good with communication! Nice clean place to stay and close to a lot of the places we were wanting to go!"
United States
Meredith T.
The price is CA $102
CA $294 total
includes taxes & fees
Jun 24 - Jun 25
Where the Trail Ends
Outdoor dining

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.
The price is CA $164
CA $366 total
includes taxes & fees
Jun 21 - Jun 22
Escape to the Blue Ridge Mountains at Wine-tergreen!
Fridge, microwave, oven, stovetop

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.
The price is CA $170
CA $429 total
includes taxes & fees
Jun 22 - Jun 23
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Property grounds

Luxury Condo in the Sky! Finest in Wintergreen!

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 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.
The price is CA $192
CA $446 total
includes taxes & fees
Jun 21 - Jun 22
Luxury Condo in the Sky! Finest in Wintergreen!
Fridge, microwave, oven, stovetop

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, (39 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is CA $146
CA $442 total
includes taxes & fees
Jun 21 - Jun 22
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (35 reviews)
"Condo was as advertised, perfect for a quick trip up to Wintergreen!"
United States
Jason L.
The price is CA $163
CA $381 total
includes taxes & fees
Jun 23 - Jun 24
Wintergreen Condo -Steps to Ski and restaurants
Interior

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, (31 reviews)
"Everything was perfect! "
United States
Danielle B.
The price is CA $141
CA $317 total
includes taxes & fees
Jul 9 - Jul 10
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Smart TV, fireplace, books

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"A great place to stay for a couple days. Small kitchen but equipped. Very clean place. Attentive service from the host."
United States
Jean H.
The price is CA $133
CA $350 total
includes taxes & fees
Jul 6 - Jul 7
Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo
1 bedroom, iron/ironing board, free WiFi, bed sheets

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.
The price is CA $121
CA $318 total
includes taxes & fees
Jun 23 - Jun 24
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
TV, fireplace

Wintergreen Ski Resort Condo w/ Golf Access!

Wintergreen Ski Resort Condo w/ Golf Access!
Roseland
10.0 out of 10, Exceptional, (2 reviews)
"It is a lovely property. Very comfortable. We had a wonderful time"
United States
Mathew M.
The price is CA $156
CA $481 total
includes taxes & fees
Jun 21 - Jun 22
Wintergreen Ski Resort Condo w/ Golf Access!
Terrace/patio

Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"The place was great and we enjoyed our stay! Super comfy and cozy. Would definitely stay again!"
United States
Christopher H.
The price is CA $177
CA $411 total
includes taxes & fees
Jun 23 - Jun 24
Cozy Lux Condo at Wintergreen Resort
Outdoor dining

Overlook 180 degree views w/Peloton!

Overlook 180 degree views w/Peloton!
Wintergreen Resort
9.4 out of 10, Exceptional, (3 reviews)
"Excellent stay. Thank you!"
United States
Kimberly B.
The price is CA $150
CA $410 total
includes taxes & fees
Jun 23 - Jun 24
Overlook 180 degree views w/Peloton!
Fridge, microwave, oven, stovetop

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.
The price is CA $191
CA $463 total
includes taxes & fees
Jun 21 - Jun 22
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
TV, fireplace

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"This was a wonderful stay, the unit was clean, comfortable, and the property managers were immediate to respond with any questions. We will definitely stay here again. The 2nd full bathroom was a plus!And the view, was breathtaking any time of day!Our stay was quiet and peaceful, just what was needed!!"
United States
Judy M.
The price is CA $196
CA $416 total
includes taxes & fees
Jun 23 - Jun 24
Mountain View Vista: Resort Condo w/ Views
Apartment, Private Bathroom (Laurelwood Hollow) | Exterior

Laurelwood Hollow

Laurelwood Hollow
2.0 star property
Nellysford
The price is CA $134
CA $363 total
includes taxes & fees
Jul 5 - Jul 6
Laurelwood Hollow
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, quiet. Spacious, good breakfast"
Cheryl 1-night trip
Posted 1 hour ago
Sleep Inn Staunton

Find out more about Middlebrook

Middlebrook Condo Rentals information

Number of reviews
933
Accommodation
333 Condo Rentals
Lowest Price
CA $294
Highest Price
CA $481

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