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

Wintergreen Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Wintergreen holiday rentals

A two-story house with a stone foundation, a large front porch, and a chimney.

1. 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, (123 reviews)
"Great home, very clean and well stocked."
United States
Rob H.
The price is HK$1,082
HK$2,193 total
includes taxes & fees
29 Sept - 30 Sept
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

2. Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (59 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
The price is HK$1,128
HK$3,443 total
includes taxes & fees
28 Sept - 29 Sept
Spacious + Serene Mtn Top Escape, 4 En Suites
A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

3. Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
9.8 out of 10, Exceptional, (60 reviews)
"Nice resort"
United States
Diana J.
The price is HK$434
HK$1,457 total
includes taxes & fees
28 Sept - 29 Sept
Where the Trail Ends
A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

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 HK$894
HK$2,008 total
includes taxes & fees
29 Sept - 30 Sept
Wintergreen Condo -Steps to Ski and restaurants
A garden with a variety of flowers and trees at dusk.

5. 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)
"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 HK$863
HK$1,894 total
includes taxes & fees
30 Sept - 1 Oct
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A wooden deck with a round table and chairs, overlooking a grassy area with trees.

6. 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.
The price is HK$911
HK$2,027 total
includes taxes & fees
28 Sept - 29 Sept
Escape to the Blue Ridge Mountains at Wine-tergreen!
A mountainous landscape with dense green forests and a clear sky.

7. 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
The price is HK$734
HK$1,899 total
includes taxes & fees
27 Sept - 28 Sept
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A spacious living area with a wooden staircase, a dining table, and a sofa.

8. Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (6 reviews)
"Cleanliness and ease of check in"
United States
Patrick
The price is HK$1,326
HK$3,250 total
includes taxes & fees
27 Sept - 28 Sept
Blackwood Chalet
A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

9. 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.
The price is HK$784
HK$1,761 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

10. "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, (43 reviews)
"Great stay and super responsive hosts! Really enjoyed my stay."
United States
Amy K.
The price is HK$812
HK$2,435 total
includes taxes & fees
28 Sept - 29 Sept
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A bedroom with a large bed, a dresser, and a ceiling fan. There are two windows providing a view of the outdoors.

11. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (15 reviews)
"Relaxing, scenic, quiet during the week, clean, modern, great communication with the host."
United States
Darlene
The price is HK$1,090
HK$2,281 total
includes taxes & fees
27 Sept - 28 Sept
Mountain View Vista: Resort Condo w/ Views
A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

12. 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.
The price is HK$1,067
HK$2,467 total
includes taxes & fees
4 Oct - 5 Oct
Luxury Condo in the Sky! Finest in Wintergreen!
A cabin with a large window, surrounded by trees.

13. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is HK$1,016
HK$2,797 total
includes taxes & fees
28 Sept - 29 Sept
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

14. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (36 reviews)
"Great stay for my family!"
United States
Joel M.
The price is HK$776
HK$1,991 total
includes taxes & fees
28 Sept - 29 Sept
Updated! Cozy and clean two bedroom condo.
A swimming pool surrounded by lush greenery and a wooden cabin.

15. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
Wintergreen Resort
10.0 out of 10, Exceptional, (4 reviews)
"This is a warm and inviting condo. We enjoyed our stay. The host provided excellent communication!"
United States
Shannon T.
The price is HK$1,600
HK$3,488 total
includes taxes & fees
25 Oct - 26 Oct
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and chairs, and a view through large windows.

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 HK$1,277
HK$3,187 total
includes taxes & fees
27 Sept - 28 Sept
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
A spacious living room with a large sectional sofa, a glass coffee table, and a dining area with wooden chairs and a table.

17. The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.2 out of 10, Wonderful, (14 reviews)
"Great location and the slopes are easily accessible!"
United States
Mark H.
The price is HK$2,010
HK$4,288 total
includes taxes & fees
7 Oct - 8 Oct
The Distinguished Squirrel Chalet walking distance
A hot tub with a wooden deck and a view of a forest.

18. Bear Tracks Cottage

Bear Tracks Cottage
2.0 star property
Nellysford
The price is HK$1,584
HK$3,364 total
includes taxes & fees
29 Sept - 30 Sept
Bear Tracks Cottage
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

19. 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.
Panoramic Peak: Wintergreen Condo with Views
A wooden pathway leading to a rustic cabin with a sign displaying the number 700-707.

20. Three Little Bears: Walk to Ski & Swim

Three Little Bears: Walk to Ski & Swim
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is HK$745
HK$2,440 total
includes taxes & fees
12 Oct - 13 Oct
Three Little Bears: Walk to Ski & Swim
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

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

10/10 Excellent
"This was a great property. Took my 90 and 85 year old cousins to stay with my husband and I so we could attend a family wedding!! Perfect place and i would book again in a heart beat!!"
Sondra M. 3-night trip
Posted 1 day ago
Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

  • View our selection of featured holiday rentals in Wintergreen
  • Use the map to find apartments and other holiday homes in the Wintergreen neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wintergreen while they last

Look no further and take a look at our great range of rental properties in Wintergreen!

Frequently asked questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Wintergreen has to offer?

Large and Luxurious Exec 5BR Chalet: This highly rated holiday home rental in Wintergreen is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Wintergreen are Wintergreen cabin, hot tub, sauna, walk to trails and Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14.

How many holiday rentals are there in Wintergreen?

Choose from 230 Expedia holiday rentals in Wintergreen for a memorable holiday.

What can I see and do in Wintergreen?

While you're exploring the area, George Washington National Forest and Humpback Rocks are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

What’s a holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.