A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Wintergreen condo rentals

Property grounds

1. 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, (158 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
The price is £189
includes taxes & fees
11 Aug - 12 Aug
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

2. 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, (121 reviews)
"Great location"
United States
Chrissy R.
The price is £219
includes taxes & fees
11 Aug - 12 Aug
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
Fireplace

3. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (59 reviews)
"Wonderful location. Wonderful host. We will be back!"
United States
April S.
The price is £153
includes taxes & fees
18 Aug - 19 Aug
Where the Trail Ends
Terrace/patio

4. 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.
The price is £198
includes taxes & fees
9 Sept - 10 Sept
Wintergreen Condo -Steps to Ski and restaurants
Outdoor dining

5. 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 £192
includes taxes & fees
11 Aug - 12 Aug
Escape to the Blue Ridge Mountains at Wine-tergreen!
Coffee/tea maker, fridge, microwave, oven

6. 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, (42 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 £232
includes taxes & fees
11 Aug - 12 Aug
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Property grounds

7. 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, (117 reviews)
"Gorgeous views! We spent most of our time out and about, but enjoyed our stay!"
United States
Jennifer P.
The price is £194
includes taxes & fees
11 Aug - 12 Aug
Endless Mountain Top Views from All The Way Up!
Dining

8. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is £218
includes taxes & fees
11 Aug - 12 Aug
Mountain View Vista: Resort Condo w/ Views
Property grounds

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

Luxury Condo in the Sky! Finest in Wintergreen!
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very clean and nicely supplied and decorated. Wonderful views from the living room! Planning on going back to this property again. "
United States
Charlie B.
The price is £237
includes taxes & fees
17 Aug - 18 Aug
Luxury Condo in the Sky! Finest in Wintergreen!
Exterior

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

Pet-Friendly Retreat Walk to Slopes & Village!
Wintergreen Resort
10.0 out of 10, Exceptional, (1 review)
"A wonderful place to stay comfortable beds. The place was nice and clean "
United States
Denise P.
The price is £216
includes taxes & fees
11 Aug - 12 Aug
Pet-Friendly Retreat Walk to Slopes & Village!
Property grounds

11. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (47 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.
The price is £221
includes taxes & fees
24 Aug - 25 Aug
Panoramic Peak: Wintergreen Condo with Views
Interior

12. 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, (33 reviews)
"Everything was perfect! "
United States
Danielle B.
The price is £161
includes taxes & fees
11 Aug - 12 Aug
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Exterior

13. 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 £201
includes taxes & fees
11 Aug - 12 Aug
Timbers Studio 46 with Wintergreen Advantage
Condo, Private Bathroom (Firefly on The Ridge) | Lounge

14. Firefly on The Ridge

Firefly on The Ridge
2.0 star property
Nellysford
The price is £254
includes taxes & fees
12 Aug - 13 Aug
Firefly on The Ridge
A mountainous landscape with dense green forests and a clear sky.

15. 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, (329 reviews)
"Awesome views and very clean condo! We had a very relaxing weekend!"
United States
Jordan O.
The price is £184
includes taxes & fees
18 Aug - 19 Aug
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Coffee/tea maker, fridge, microwave, oven

16. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (39 reviews)
"We had an incredible stay this past week. The condo "
United States
Holly M.
The price is £305
includes taxes & fees
12 Aug - 13 Aug
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Exterior

17. Vistas 71 with Wintergreen Advantage

Vistas 71 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"Love to escape to Wintergreen anytime of the year!!!"
United States
Annemarie T.
The price is £269
includes taxes & fees
16 Aug - 17 Aug
Vistas 71 with Wintergreen Advantage
Exterior

18. Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great location and cozy condo! "
United States
Molly M.
The price is £232
includes taxes & fees
11 Aug - 12 Aug
Diamond Hill Studio 09 with Wintergreen Advantage
Exterior

19. Mountain Inn Lodge 71 with Wintergreen Advantage

Mountain Inn Lodge 71 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, nice facilities.. polite staff "
United States
Rich C.
The price is £220
includes taxes & fees
11 Aug - 12 Aug
Mountain Inn Lodge 71 with Wintergreen Advantage
Terrace/patio

20. 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 £218
includes taxes & fees
16 Aug - 17 Aug
Cozy Lux Condo at Wintergreen Resort
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 Wintergreen Hotel Reviews

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

10/10 Excellent
"Our stay at the property was amazing! Everything in the description was absolutely on point except for the views. They were so much better, but thats to be expected as those views are hard to describe! My family spent most of the time on the porch! The hosts were very helpful and very quick to respond! Overall a 5 star stay! We definitely recommed this condo and hope to come back here on our next vivst!"
Elliot P. 2-night trip
Posted 10 hours ago
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Find out more about Wintergreen

Wintergreen Condo Rentals information

Number of reviews
1,174
Accommodation
330 Condo Rentals
Lowest Price
£153
Highest Price
£305

Frequently asked questions

How much do condos in Wintergreen cost?
You can expect to pay from £153 to £305 per night for condos in Wintergreen. No matter your budget, a terrific stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your condo in Wintergreen with Expedia?
Booking a condo in Wintergreen is as simple as clicking on your travel dates and selecting a place suited to your needs. Chasing something low cost or luxurious, or a property that also comes with a pool and free WiFi? Use Expedia's search filters to narrow your results even further and find your dream fit.
How can I find cheap condos in Wintergreen?
Expedia can help you easily source cheap condos in Wintergreen. To lock in a terrific stay in a matter of clicks, try out our handy filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Wintergreen near my condo?
The ideal travel accessory is a well-planned to-do list. Wintergreen Resort is a good spot to kick-start your sightseeing in Wintergreen.