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 wooden deck with a round table and chairs, overlooking a grassy area with trees.

1. 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 NZ$447
includes taxes & fees
20 Oct - 21 Oct
Escape to the Blue Ridge Mountains at Wine-tergreen!
A spacious living area with a wooden staircase, a dining table, and a sofa.

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 NZ$818
includes taxes & fees
20 Oct - 21 Oct
Blackwood Chalet
Private kitchen

3. "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 NZ$541
includes taxes & fees
20 Oct - 21 Oct
"Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining
A mountainous landscape with dense green forests and a clear sky.

4. 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 NZ$437
includes taxes & fees
25 Oct - 26 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

5. 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 NZ$441
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.

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)
"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 NZ$441
includes taxes & fees
20 Oct - 21 Oct
Walk to Market/Private community outdoor pool!
A staircase with a wooden handrail and a carpeted landing.

7. 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 NZ$624
includes taxes & fees
20 Oct - 21 Oct
Three Little Bears: Walk to Ski & Swim
A garden with a variety of flowers and trees at dusk.

8. 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 NZ$431
includes taxes & fees
1 Nov - 2 Nov
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
A two-story house with a stone foundation, a large front porch, and a chimney.

9. 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 NZ$577
includes taxes & fees
22 Oct - 23 Oct
Cozy Wintergreen Ski Resort Retreat • Panoramic Views • Fireplace
A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

10. 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 NZ$567
includes taxes & fees
16 Nov - 17 Nov
Panoramic Peak: Wintergreen Condo with Views
A modern living room with a grey sofa set, a coffee table, and a fireplace.

11. Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.6 out of 10, Exceptional, (16 reviews)
"A beautiful property with spectacular mountains view, sunrise and many stars at night. Really enjoyed the stay."
United States
Harumi
The price is NZ$595
includes taxes & fees
20 Oct - 21 Oct
Mountain View Vista: Resort Condo w/ Views
A bedroom with a four-poster bed, a television on a wooden cabinet, and a view of greenery through a window.

12. 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 NZ$1,019
includes taxes & fees
30 Oct - 31 Oct
Serenity Cabin-Woodland Retreat
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 NZ$513
includes taxes & fees
20 Oct - 21 Oct
Pet-Friendly Retreat Walk to Slopes & Village!
A room with two armchairs, a small table with a lamp, and a view of a balcony with a railing.

14. 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 NZ$666
includes taxes & fees
20 Oct - 21 Oct
Spacious + Serene Mtn Top Escape, 4 En Suites
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.
2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.
A cabin with a large window, surrounded by trees.

16. 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 NZ$655
includes taxes & fees
16 Nov - 17 Nov
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and chairs, and a view through large windows.

17. 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.
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
A modern kitchen with white cabinetry, a large island with bar stools, stainless steel appliances, and a chandelier.

18. 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 NZ$727
includes taxes & fees
3 Nov - 4 Nov
Your Ski-In and Ski-Out Wintergreen Escape
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.

19. 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 NZ$437
includes taxes & fees
19 Nov - 20 Nov
Mountain Inn Lodge 77 with Wintergreen Advantage
A modern kitchen with white cabinetry, a black stove, and a dining area with a chandelier.

20. 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 NZ$650
includes taxes & fees
18 Nov - 19 Nov
Wintergreen Resort - Ski Slopes, Hike, Swim, & Golf
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 22 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 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 NZ$431 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.