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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Wintergreen holiday rentals

A garden with a variety of flowers and trees at dusk.

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, (161 reviews)
"It was a beautiful stay - we enjoyed the place and wished we could have stayed one more day to soak up the surroundings of the area more!"
United States
Michelle W.
The price is AU$365
includes taxes & fees
1 Nov - 2 Nov
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.

2. 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 AU$364
includes taxes & fees
20 Oct - 21 Oct
Escape to the Blue Ridge Mountains at Wine-tergreen!
A mountainous landscape with dense green forests and a clear sky.

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, (337 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is AU$369
includes taxes & fees
3 Nov - 4 Nov
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A spacious living room with a sofa, coffee table, and a dining area with a kitchen in the background.

4. Updated! Cozy and clean two bedroom condo.

Updated! Cozy and clean two bedroom condo.
Wintergreen Resort
9.2 out of 10, Wonderful, (37 reviews)
"Great stay for my family!"
United States
Joel M.
The price is AU$368
includes taxes & fees
20 Oct - 21 Oct
Updated! Cozy and clean two bedroom condo.
A two-story wooden cabin with a wooden deck and a small porch.

5. Walk to Market/Private community outdoor pool!

Walk to Market/Private community outdoor pool!
Wintergreen Resort
9.8 out of 10, Exceptional, (85 reviews)
"Very nice, looks like a new home, comfortable. But as it is a mountain resort watch for bears, we had one walk right near the car, we were glad we were inside the car at that time."
United States
Robyn M.
The price is AU$371
includes taxes & fees
20 Oct - 21 Oct
Walk to Market/Private community outdoor pool!
A cabin with a steeply pitched roof, wooden exterior, and a deck with stairs leading to a porch.

6. Three Little Bears

Three Little Bears
2.0 star property
Nellysford
The price is AU$453
includes taxes & fees
20 Oct - 21 Oct
Three Little Bears
Private kitchen

7. "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 AU$445
includes taxes & fees
20 Oct - 21 Oct
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A two-story house with a stone foundation, a large front porch, and a chimney.

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

Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (126 reviews)
"Nice condo in a nice resort. House has everything you need and more."
United States
Thomas B.
The price is AU$469
includes taxes & fees
22 Oct - 23 Oct
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

9. 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
The price is AU$535
includes taxes & fees
20 Oct - 21 Oct
Spacious + Serene Mtn Top Escape, 4 En Suites
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.

10. Mountain Inn Lodge 77 with Wintergreen Advantage

Mountain Inn Lodge 77 with Wintergreen Advantage
Wintergreen
8.0 out of 10, Very good, (1 review)
"The stairs inside the property makes hard to lug the suitcases around little hard."
United States
Bhaskar
The price is AU$371
includes taxes & fees
1 Nov - 2 Nov
Mountain Inn Lodge 77 with Wintergreen Advantage
An aerial view of a large estate with multiple buildings surrounded by dense forest and mountains in the background.

11. Mountain Inn Studio 93 with Wintergreen Advantage

Mountain Inn Studio 93 with Wintergreen Advantage
Wintergreen
The price is AU$351
includes taxes & fees
1 Nov - 2 Nov
Mountain Inn Studio 93 with Wintergreen Advantage
Exterior

12. 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 AU$332
includes taxes & fees
1 Nov - 2 Nov
Timbers Studio 46 with Wintergreen Advantage
A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

13. 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 AU$428
includes taxes & fees
9 Nov - 10 Nov
Pet-Friendly Retreat Walk to Slopes & Village!
A covered patio area with a glass door leading to an outdoor seating area.

14. 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, (8 reviews)
The price is AU$488
includes taxes & fees
18 Nov - 19 Nov
Treetop Sunset Deck, 2 Upscale King Bedrooms, Fireplace, Walk to Spa & Trails
Exterior

15. Mountain Inn Lodge 55 with Wintergreen Advantage

Mountain Inn Lodge 55 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (1 review)
"The condo is located very close to the ski slopes and several restaurants. Good for a short weekend stay!"
United States
Sarah H.
The price is AU$371
includes taxes & fees
1 Nov - 2 Nov
Mountain Inn Lodge 55 with Wintergreen Advantage
A bedroom with a large bed, a wooden dresser, and a view of the landscape through large windows.

16. 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 AU$411
includes taxes & fees
16 Nov - 17 Nov
Panoramic Peak
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

17. 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 AU$476
includes taxes & fees
1 Nov - 2 Nov
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
A covered outdoor deck with a round table and chairs, overlooking a lush landscape.

18. 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 AU$563
includes taxes & fees
21 Oct - 22 Oct
Overlook 180 degree views w/Peloton!
Exterior

19. 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 AU$390
includes taxes & fees
1 Nov - 2 Nov
Diamond Hill Studio 09 with Wintergreen Advantage
An aerial view of a large estate with multiple buildings surrounded by dense forest and mountains in the background.

20. Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
The price is AU$407
includes taxes & fees
1 Nov - 2 Nov
Three Ridges 64 With Wintergreen Advantage
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

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

10/10 Excellent
"We were so fortunate to find this spectacular gem! The breathtaking views that pictures just cannot do justice for were amazing! The unit was so well stocked with all the essentials and one of the cleanest places we have stayed. Check-in and check-out were clear and simple. We can’t wait to book again. Thank you for sharing your piece of mountain with us. We loved it."
Traci A. 3-night trip
Posted 20 hours ago
Best views on Mountain! Breathtaking 5 Star condo! Available October 2-4 weekend

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, 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 favourite 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 depend 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 AU$364 per night. Entering your travel dates in the search wizard might find you 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.