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

Holiday Rentals in Wintergreen

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Our top choices for Wintergreen holiday rentals

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 €223
includes taxes & fees
9 Nov - 10 Nov
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2. 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 €379
includes taxes & fees
9 Nov - 10 Nov
Blackwood Chalet

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 €221
includes taxes & fees
12 Nov - 13 Nov
Updated! Cozy and clean two bedroom condo.

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, (129 reviews)
"Clean property that was well equipped, and easy check in."
United States
Joseph Blaine
The price is €211
includes taxes & fees
9 Nov - 10 Nov
2 minutes from the shops and activities; Cozy 1 bedroom end unit.

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 €222
includes taxes & fees
11 Nov - 12 Nov
Escape to the Blue Ridge Mountains at Wine-tergreen!

6. 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 €250
includes taxes & fees
9 Nov - 10 Nov
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace

7. 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 €231
includes taxes & fees
12 Nov - 13 Nov
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

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

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (61 reviews)
"Awesome location with 4 bed, 4 bath. Lots of room."
United States
Maija
Spacious + Serene Mtn Top Escape, 4 En Suites

9. Three Little Bears: Walk to Ski & Swim

Three Little Bears: Walk to Ski & Swim
Wintergreen Resort
9.6 out of 10, Exceptional, (14 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is €294
includes taxes & fees
9 Nov - 10 Nov
Three Little Bears: Walk to Ski & Swim

10. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (39 reviews)
"It was a fine place for our family to stay during our staycation!"
United States
Alicia G.
The price is €261
includes taxes & fees
10 Nov - 11 Nov
Wintergreen Condo -Steps to Ski and restaurants

11. "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 €296
includes taxes & fees
9 Nov - 10 Nov
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

12. Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (49 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 €267
includes taxes & fees
16 Nov - 17 Nov
Panoramic Peak: Wintergreen Condo with Views

13. 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 €277
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo in the Sky! Finest in Wintergreen!

14. 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 €221
includes taxes & fees
12 Nov - 13 Nov
Walk to Market/Private community outdoor pool!

15. Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
9.8 out of 10, Exceptional, (18 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
The price is €394
includes taxes & fees
9 Nov - 10 Nov
Serenity Cabin-Woodland Retreat

16. 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.
The price is €272
includes taxes & fees
9 Nov - 10 Nov
Endless Mountain Top Views from All The Way Up!

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.
Pet-Friendly Retreat Walk to Slopes & Village!

18. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Very organized information and amazing communication from host ahead of arrival; the view and location are amazing, and the accommodations were comfortable and made for an easy and fun adventure! Will definitely stay here again. "
United States
Blayre G.
The price is €388
includes taxes & fees
9 Nov - 10 Nov
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

19. Your Ski-In and Ski-Out Wintergreen Escape

Your Ski-In and Ski-Out Wintergreen Escape
Wintergreen Resort
10.0 out of 10, Exceptional, (2 reviews)
"Awesome place!"
United States
Chris C.
The price is €461
includes taxes & fees
8 Dec - 9 Dec
Your Ski-In and Ski-Out Wintergreen Escape

20. 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.
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
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

Find out more about Wintergreen

Everything you need to know about Wintergreen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Wintergreen holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wintergreen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen holiday rentals we have selected for you start as low as €221 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Wintergreen cabin, hot tub, sauna, walk to trails: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Wintergreen are Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 and Remodeled 3BR/2BA Ski Chalet off Tyro Slope.

How many holiday rentals are there in Wintergreen?

Choose from 232 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.