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Our top choices for Middlebrook condo rentals
1. 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, (129 reviews)
"Clean property that was well equipped, and easy check in."
Joseph Blaine
The price is CA $138
CA $317 total
includes taxes & fees
Nov 8 - Nov 9
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-friendlyRoseland
9.6 out of 10, Exceptional, (163 reviews)
"Perfect condo for couple. Two bathrooms, big kitchen, big porch, big living area."
Kathleen K.
The price is CA $154
CA $331 total
includes taxes & fees
Nov 16 - Nov 17
3. 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, (338 reviews)
"We enjoyed our time at the stay. "
michael b.
The price is CA $131
CA $334 total
includes taxes & fees
Nov 9 - Nov 10
4. 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!"
Joel M.
The price is CA $138
CA $323 total
includes taxes & fees
Nov 16 - Nov 17
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!"
Jennifer D.
The price is CA $162
CA $344 total
includes taxes & fees
Nov 11 - Nov 12
6. 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."
Alice W.
The price is CA $138
CA $333 total
includes taxes & fees
Nov 8 - Nov 9
7. Panoramic Peak
Panoramic PeakNellysford
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."
Carrie
The price is CA $245
CA $416 total
includes taxes & fees
Nov 24 - Nov 25
8. Timbers Studio 46 with Wintergreen Advantage
Timbers Studio 46 with Wintergreen AdvantageWintergreen
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...
Madison D.
The price is CA $180
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
9. Mountain Inn Studio 96 with Wintergreen Advantage
Mountain Inn Studio 96 with Wintergreen AdvantageWintergreen
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. "
Lana
The price is CA $180
CA $301 total
includes taxes & fees
Nov 22 - Nov 23
10. Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Condo -Steps to Ski and restaurantsWintergreen Resort
9.8 out of 10, Exceptional, (39 reviews)
"It was a fine place for our family to stay during our staycation!"
Alicia G.
The price is CA $186
CA $403 total
includes taxes & fees
Nov 7 - Nov 8
11. Mountain Inn Lodge 79 with Wintergreen Advantage
Mountain Inn Lodge 79 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
"The Wintergreen resort is beautiful, and this rented condo more than met our expectations. It was very clean and well-stocked with dishes/cookware/utensils/Keurig coffee machine, towels, hair dryers (2), and toiletries. The unit has two TVs complete with 123 cable channels. The bed in the loft is very comfortable. We plan to stay there again in the future. "
Marlena E B.
The price is CA $194
CA $332 total
includes taxes & fees
Nov 8 - Nov 9
12. Northridge 07 With Wintergreen Advantage
Northridge 07 With Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
"Good Stay! Clean, need to have a lock on master bathroom. Door slides"
William M.
The price is CA $208
CA $372 total
includes taxes & fees
Nov 9 - Nov 10
13. Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • FireplaceWintergreen Resort
10.0 out of 10, Exceptional, (128 reviews)
"Nice condo in a nice resort. House has everything you need and more."
Thomas B.
The price is CA $190
CA $383 total
includes taxes & fees
Nov 9 - Nov 10
14. Diamond Hill Studio 09 with Wintergreen Advantage
Diamond Hill Studio 09 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great location and cozy condo! "
Molly M.
The price is CA $222
CA $358 total
includes taxes & fees
Nov 8 - Nov 9
15. 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 "
Denise P.
The price is CA $157
CA $380 total
includes taxes & fees
Nov 9 - Nov 10
16. Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
Wintergreen Resort - Ski Slopes, Hike, Swim, & GolfWintergreen 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. "
Sarah L.
The price is CA $157
CA $380 total
includes taxes & fees
Nov 9 - Nov 10
17. Mountain View Vista
Mountain View VistaNellysford
The price is CA $246
CA $418 total
includes taxes & fees
Nov 15 - Nov 16
18. Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & TrailsWintergreen Resort
10.0 out of 10, Exceptional, (9 reviews)
The price is CA $203
CA $443 total
includes taxes & fees
Nov 18 - Nov 19
19. Timbers Lodge 49 with Wintergreen Advantage
Timbers Lodge 49 with Wintergreen AdvantageWintergreen
10.0 out of 10, Exceptional, (1 review)
"Condo is greatCheck in and out easy"
Mike G.
The price is CA $236
CA $378 total
includes taxes & fees
Nov 15 - Nov 16
20. "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 & diningWintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
Amy K.
The price is CA $194
CA $486 total
includes taxes & fees
Nov 9 - Nov 10
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.
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.
Photo by Brittany Davidson
Open Photo by Brittany Davidson