Photo by Melissa Smestad

Holiday Rentals in Wintergreen

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Our top choices for Wintergreen holiday rentals

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
The price is €241
includes taxes & fees
13 Jan - 14 Jan 2026
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
2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (2)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is €228
includes taxes & fees
21 Jan - 22 Jan 2026
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (36)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is €241
includes taxes & fees
13 Jan - 14 Jan 2026
The Modern Mountain Condo

Wintergreen. Sunset Vista Villa - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen Resort
10.0 out of 10, Exceptional, (94)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is €302
includes taxes & fees
12 Jan - 13 Jan 2026
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Nellysford
10.0 out of 10, Exceptional, (23)
"The house was so nice and clean and the host was great also and we had a great stay and would highly recommend it. "
United States
Jody W.
The price is €402
includes taxes & fees
14 Jan - 15 Jan 2026
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
2.0 star property
Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is €322
includes taxes & fees
13 Jan - 14 Jan 2026
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,

Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,
2.0 star property
Wintergreen Resort
The price is €298
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,

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, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is €231
includes taxes & fees
5 Jan - 6 Jan 2026
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (30)
"Great location, beautiful home and so much to do nearby."
United States
Jordan D.
The price is €374
includes taxes & fees
13 Jan - 14 Jan 2026
Bear Tracks Cottage: New Hot Tub + Fire Pit

Design-Lover’s Getaway • Game Room • Hot Tub

Design-Lover’s Getaway • Game Room • Hot Tub
Wintergreen Resort
9.8 out of 10, Exceptional, (6)
"Peaceful family trip. The cabin was beautiful, lots of space, and very clean. The cabin had everything we needed. The game room, board games and puzzles were a hit with our kids. Hot tub was huge, clean had its own separate gated area. "
United States
Victoria R.
The price is €508
includes taxes & fees
7 Jan - 8 Jan 2026
Design-Lover’s Getaway • Game Room • Hot Tub

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, (304)
"Great view!!"
United States
Suzanne W.
The price is €210
includes taxes & fees
4 Jan - 5 Jan 2026
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, (22)
"Great communication from the startReturn texts the same day on any questionsGreat location for our tripVery cleanViews around property are greatNice restaurant A plus for what we neededDog friendly Thanks againHope to be back"
United States
Phil P.
The price is €219
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

"Glass & Pine" Home close to Bold Rock & Vineyards

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (2)
"We only stayed one night but wished we could have stayed longer! The place was super clean and the views were beautiful once the rain finally stopped! Close to our favorite brewery and cidery. There were issues with TV reception (buffering) which may just be the area. Not much time for TV watching anyway with all the beautiful things to explore. We enjoyed our stay. "
United States
Robert H.
The price is €378
includes taxes & fees
13 Jan - 14 Jan 2026
"Glass & Pine" Home close to Bold Rock & Vineyards

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is €351
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (3)
"Great house and great host!"
United States
Joe B.
The price is €385
includes taxes & fees
7 Jan - 8 Jan 2026
Serenity Cabin-Woodland Retreat

Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24

Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24
2.0 star property
Chestnut Springs
10.0 out of 10, Exceptional, (1)
The price is €1,806
includes taxes & fees
6 Jan - 7 Jan 2026
Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (8)
"Beautiful view!"
United States
Serge L.
The price is €263
includes taxes & fees
14 Jan - 15 Jan 2026
Mountain View Vista: Resort Condo w/ Views

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (4)
"Will definitely stay at this location again!!"
United States
Richard W.
The price is €355
includes taxes & fees
12 Jan - 13 Jan 2026
Lofty Pursuits: Spectacular View + EV Charger

Overlook 180 degree views w/Peloton!

Overlook 180 degree views w/Peloton!
Wintergreen Resort
9.4 out of 10, Exceptional, (3)
"Excellent stay. Thank you!"
United States
Kimberly B.
The price is €331
includes taxes & fees
13 Jan - 14 Jan 2026
Overlook 180 degree views w/Peloton!

Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
Chestnut Springs
10.0 out of 10, Exceptional, (15)
"Great stay!"
United States
Cheryl P.
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
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 €210 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?

Warren’s Woods! Cozy 5-bedroom house in lovely Wintergreen.AVAIL over Christmas!: This highly rated holiday home rental in Wintergreen offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Some other top choices in Wintergreen are Upscale and Family-Friendly in Wintergreen and Large and Luxurious Exec 5BR Chalet.

How many holiday rentals are there in Wintergreen?

Choose from 231 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.