Photo by Brittany Davidson

Search Condos Rentals in Middlebrook from CA $132

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Nov 20 - Nov 22
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Dec 11 - Dec 13
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Jan 8 - Jan 10

Our top choices for Middlebrook condo rentals

A balcony with a table and chairs, offering a view of a mountainous landscape.

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, (339 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is CA $132
CA $337 total
includes taxes & fees
Nov 11 - Nov 12
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A garden with a variety of flowers and trees at dusk.

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, (163 reviews)
"Perfect condo for couple. Two bathrooms, big kitchen, big porch, big living area."
United States
Kathleen K.
The price is CA $155
CA $344 total
includes taxes & fees
Nov 12 - Nov 13
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.

3. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (38 reviews)
"Great stay for my family!"
United States
Joel M.
The price is CA $140
CA $336 total
includes taxes & fees
Nov 12 - Nov 13
Updated! Cozy and clean two bedroom condo.
A two-story house with a front porch, a mailbox, and a wooden fence.

4. 2 minutes from the shops and activities; Cozy 1 bedroom end unit.

2 minutes from the shops and activities; Cozy 1 bedroom end unit.
Wintergreen
9.4 out of 10, Exceptional, (131 reviews)
"Awesome location. Cool set up and perfect for a couples getaway. The wood burning fireplace was a great thing."
United States
Paul
The price is CA $140
CA $320 total
includes taxes & fees
Nov 11 - Nov 12
2 minutes from the shops and activities; Cozy 1 bedroom end unit.
A set of stone steps leading up to a house with a light-colored exterior.

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

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.6 out of 10, Exceptional, (132 reviews)
"Close to Ski lifts and great for a weekend stay!"
United States
Jennifer D.
The price is CA $164
CA $347 total
includes taxes & fees
Nov 11 - Nov 12
Escape to the Blue Ridge Mountains at Wine-tergreen!
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

6. Panoramic Peak

Panoramic Peak
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (1 review)
"The place was absolutely beautiful and spotless. The view was amazing. The only issue we had was when we asked where it was. We were told Nellysford and didn’t really understand that it was part of the Wintergreen resort so it was much further away from our actual destination. But the place was really amazing. We would stay there again."
United States
Carrie
The price is CA $232
CA $403 total
includes taxes & fees
Nov 24 - Nov 25
Panoramic Peak
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

7. 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 $188
CA $419 total
includes taxes & fees
Nov 16 - Nov 17
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (48 reviews)
"Views were amazing!"
United States
Sang Rea
The price is CA $201
CA $435 total
includes taxes & fees
Nov 11 - Nov 12
Luxury Condo in the Sky! Finest in Wintergreen!
Gather around the stone fireplace after a day on the mountain, with a large-screen TV above and the deck just steps away.

9. 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, (9 reviews)
The price is CA $178
CA $423 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (128 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
The price is CA $206
CA $402 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A two-story wooden cabin with a wooden deck and a small porch.

11. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (86 reviews)
"What a gem of a place! We had a wonderful long weekend get away as a family. The host communicated clearly and timely. We loved our stay here!"
United States
Christy P.
The price is CA $140
CA $336 total
includes taxes & fees
Nov 12 - Nov 13
Walk to Market/Private community outdoor pool!
An aerial view of a residential area with multiple houses surrounded by dense forest, featuring a central building with a prominent roof and a well-lit driveway.

12. 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.
The price is CA $210
CA $376 total
includes taxes & fees
Nov 12 - Nov 13
Northridge 07 With Wintergreen Advantage
Exterior

13. Mountain Inn Lodge 78 with Wintergreen Advantage

Mountain Inn Lodge 78 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"Had so much fun! Perfect stay!"
United States
Megan O.
The price is CA $196
CA $336 total
includes taxes & fees
Nov 14 - Nov 15
Mountain Inn Lodge 78 with Wintergreen Advantage
A covered outdoor deck with a round table and chairs, overlooking a lush landscape.

14. 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 $216
CA $503 total
includes taxes & fees
Nov 11 - Nov 12
Overlook 180 degree views w/Peloton!
Exterior

15. 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.
The price is CA $182
CA $301 total
includes taxes & fees
Nov 11 - Nov 12
Timbers Studio 46 with Wintergreen Advantage
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
The price is CA $249
CA $422 total
includes taxes & fees
Nov 11 - Nov 12
Mountain View Vista
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

17. 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.
The price is CA $158
CA $384 total
includes taxes & fees
Nov 11 - Nov 12
Pet-Friendly Retreat Walk to Slopes & Village!
Exterior

18. Mountain Inn Studio 96 with Wintergreen Advantage

Mountain Inn Studio 96 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
The price is CA $182
CA $301 total
includes taxes & fees
Nov 11 - Nov 12
Mountain Inn Studio 96 with Wintergreen Advantage
Private kitchen

19. "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.
The price is CA $184
CA $477 total
includes taxes & fees
Nov 16 - Nov 17
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A wooden deck with two Adirondack chairs facing a scenic view of a sunset over a mountainous landscape.

20. 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, (125 reviews)
"Wow, they thought of everything you could need. This was one of the nicest places we have stayed. The price was amazing too. Definitely stay again"
United States
Sara C.
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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Learn more about Middlebrook

Nestled in Virginia's scenic countryside, this charming village offers easy access to the fascinating Frontier Culture Museum and captivating performances at the American Shakespeare Centre. History buffs can explore The Woodrow Wilson Presidential Library nearby, while outdoor enthusiasts will appreciate the natural splendour of George Washington National Forest and Sherando Lake Recreation Area.

See all hotels in Middlebrook
A snow-covered road winding through a forest with bare trees.
Photo by Brittany Davidson
Open Photo by Brittany Davidson

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