Holiday Rentals in Wintergreen

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Our top choices for Wintergreen holiday rentals

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (34 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is €227
includes taxes & fees
11 May - 12 May
Wintergreen Condo -Steps to Ski and restaurants

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, (152 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is €214
includes taxes & fees
11 May - 12 May
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
Spacious + Serene Mtn Top Escape, 4 En Suites

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, (103 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
The price is €211
includes taxes & fees
12 May - 13 May
Endless Mountain Top Views from All The Way Up!

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (111 reviews)
"Great and comfortable place to stay! Host was very welcoming and responsive. "
United States
Jon L.
The price is €280
includes taxes & fees
12 May - 13 May
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is €241
includes taxes & fees
11 May - 12 May
Laurelwood Hollow: Walk to Ski & Swim

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is €188
includes taxes & fees
11 May - 12 May
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is €274
includes taxes & fees
11 May - 12 May
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Where the Trail Ends

Where the Trail Ends
Wintergreen Resort
10.0 out of 10, Exceptional, (49 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
The price is €199
includes taxes & fees
11 May - 12 May
Where the Trail Ends

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, (127 reviews)
"great stay"
United States
Vickie G.
The price is €220
includes taxes & fees
11 May - 12 May
Escape to the Blue Ridge Mountains at Wine-tergreen!

Mountain Inn Studio 94 with Wintergreen Advantage

Mountain Inn Studio 94 with Wintergreen Advantage
Wintergreen
Mountain Inn Studio 94 with Wintergreen Advantage

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
The price is €349
includes taxes & fees
12 May - 13 May
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay with great communication with the host "
United States
Annamarie P.
The price is €321
includes taxes & fees
11 May - 12 May
Serenity Cabin-Woodland Retreat

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
The price is €258
includes taxes & fees
11 May - 12 May
Three Ridges 64 With Wintergreen Advantage

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, (320 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
The price is €218
includes taxes & fees
25 May - 26 May
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
The price is €215
includes taxes & fees
17 May - 18 May
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Cozy Lux Condo at Wintergreen Resort

Cozy Lux Condo at Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed it so much! So cozy and close to the resort! "
United States
Katie B.
Cozy Lux Condo at Wintergreen Resort

Mountain Inn Lodge 54 with Wintergreen Advantage

Mountain Inn Lodge 54 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"We were in the area looking to possibly relocate and this loft on the mountain was a beautiful stay. Convenient to restaurants within walking distance. We would definitely book again!"
United States
Erin C.
The price is €218
includes taxes & fees
11 May - 12 May
Mountain Inn Lodge 54 with Wintergreen Advantage

Renovated Wintergreen Condo with Pool Access, and more!

Renovated Wintergreen Condo with Pool Access, and more!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
Renovated Wintergreen Condo with Pool Access, and more!

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, (32 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
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 €199 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?

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Wintergreen are 4 BR cabin mins to trails & breweries pets welcome and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many holiday rentals are there in Wintergreen?

Choose from 223 Expedia holiday rentals in Wintergreen for a memorable holiday.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. While here, Bold Rock Hard Cider Nellysford Cidery and Stoney Creek Golf Course 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.