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Wintergreen Vacation Rentals

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Jan 10 - Jan 11
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Jan 11 - Jan 12
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Jan 16 - Jan 18
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Jan 23 - Jan 25

Our top choices for Wintergreen vacation rentals

Exterior
Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥15,000
￥44,076 total
includes taxes & fees
Jan 11 - Jan 12
Laurelwood Hollow: Walk to Ski & Swim
Property grounds
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

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, (4 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is ￥13,980
￥35,610 total
includes taxes & fees
Jan 11 - Jan 12
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Fridge, microwave, oven, stovetop
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

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

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
2.0 star property
Wintergreen Resort
9.8 out of 10, Exceptional, (7 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is ￥18,828
￥47,574 total
includes taxes & fees
Jan 11 - Jan 12
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Fireplace
The Modern Mountain Condo

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is ￥14,886
￥36,397 total
includes taxes & fees
Jan 12 - Jan 13
The Modern Mountain Condo
Cabin, Private Bathroom (Blackwood Chalet) | Lounge
Blackwood Chalet

Blackwood Chalet

Blackwood Chalet
2.0 star property
Nellysford
10.0 out of 10, Exceptional, (3 reviews)
"Love the area"
United States
Toni
The price is ￥28,262
￥63,317 total
includes taxes & fees
Jan 12 - Jan 13
Blackwood Chalet
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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, (306 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is ￥16,239
￥37,797 total
includes taxes & fees
Jan 13 - Jan 14
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Property grounds
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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (144 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is ￥19,142
￥41,055 total
includes taxes & fees
Jan 11 - Jan 12
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Terrace/patio
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

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 reviews)
"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 ￥29,841
￥72,875 total
includes taxes & fees
Jan 11 - Jan 12
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Fridge, microwave, oven, stovetop
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

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, (26 reviews)
"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 ￥17,651
￥50,660 total
includes taxes & fees
Jan 13 - Jan 14
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Exterior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

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, (95 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is ￥29,027
￥55,151 total
includes taxes & fees
Jan 13 - Jan 14
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Interior
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

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (24 reviews)
"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 ￥18,828
￥38,941 total
includes taxes & fees
Jan 11 - Jan 12
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Property grounds
Spacious 3BR 3BA Pet Friendly Resort Condo

Spacious 3BR 3BA Pet Friendly Resort Condo

Spacious 3BR 3BA Pet Friendly Resort Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"Awesome just Awesome place. Definitely recommend this place. Very well taken care of and everything you needed all rolled into one place. Thank you so much again and we will definitely be coming back. "
United States
Lance B.
The price is ￥35,303
￥74,533 total
includes taxes & fees
Jan 11 - Jan 12
Spacious 3BR 3BA Pet Friendly Resort Condo
Smart TV
Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (3 reviews)
"Great house and great host!"
United States
Joe B.
The price is ￥17,259
￥56,737 total
includes taxes & fees
Jan 14 - Jan 15
Serenity Cabin-Woodland Retreat
Exterior
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!

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (25 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is ￥21,520
￥57,645 total
includes taxes & fees
Jan 13 - Jan 14
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
TV, fireplace
Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful view!"
United States
Serge L.
The price is ￥21,947
￥45,924 total
includes taxes & fees
Jan 12 - Jan 13
Mountain View Vista: Resort Condo w/ Views
Exterior detail
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Wintergreen Resort
10.0 out of 10, Exceptional, (40 reviews)
"Amazing stay! Space was clean, well stocked and easy to enter. Host was very responsive and gave lots of helpful information. Would recommend and stay again!"
United States
Sonja S.
The price is ￥17,651
￥41,319 total
includes taxes & fees
Jan 14 - Jan 15
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking
Outdoor spa tub
Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
The price is ￥28,713
￥68,014 total
includes taxes & fees
Jan 11 - Jan 12
Bear Tracks Cottage: New Hot Tub + Fire Pit
Dining
"Glass & Pine" Home close to Bold Rock & Vineyards

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

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥30,478
￥69,629 total
includes taxes & fees
Jan 13 - Jan 14
"Glass & Pine" Home close to Bold Rock & Vineyards
Outdoor dining
Overlook 180 degree views w/Peloton!

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 ￥21,552
￥53,967 total
includes taxes & fees
Jan 13 - Jan 14
Overlook 180 degree views w/Peloton!
Interior
Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger

Lofty Pursuits: Spectacular View + EV Charger
Treeloft
10.0 out of 10, Exceptional, (6 reviews)
"Will definitely stay at this location again!!"
United States
Richard W.
The price is ￥27,458
￥61,818 total
includes taxes & fees
Jan 14 - Jan 15
Lofty Pursuits: Spectacular View + EV Charger
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

"SERENITY 4 ALL SEASONS"

"SERENITY 4 ALL SEASONS"

10/10 Excellent
"We thoroughly enjoyed this well stocked and comfortable home. The home is in a beautiful location nestled within the trees. The bedrooms offer a variety of sleeping arrangements and the beds were comfortable. Thanks for a great new years! "
Anne C. 2-night trip
Posted 5 days ago
"SERENITY 4 ALL SEASONS"

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

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Look no further and take a look at our great range of rental properties in Wintergreen!

Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

What are some of the best vacation rentals that Wintergreen has to offer?

Unbeatable Views Atop Wintergreen Resort: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Some other top choices in Wintergreen are 2min to Ski Hot Tub EV Charger Mountain View DogOK and Upscale and Family-Friendly in Wintergreen.

How many vacation rentals are there in Wintergreen?

Choose from 231 Expedia vacation rentals in Wintergreen for a memorable vacation.

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 vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.