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Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Wintergreen vacation rentals

Exterior
Laurelwood Hollow: Walk to Ski & Swim

Apartment in Wintergreen Resort

Laurelwood Hollow: Walk to Ski & Swim
10.0 out of 10, Exceptional, (3)
"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 ￥14,900
￥43,782 total
includes taxes & fees
Jan 13 - Jan 14
Laurelwood Hollow: Walk to Ski & Swim
Smart TV, fireplace, books
Stylish-Updated-Central -Walk to Slopes-Dogs OK!

Condo in Wintergreen Resort

Stylish-Updated-Central -Walk to Slopes-Dogs OK!
9.8 out of 10, Exceptional, (30)
"This was a great place for our short weekend getaway! We needed a place we could unplug, and that's exactly what we did reading by the fire, but there was plenty to do if we wanted to! We look forward to staying here again."
United States
Richard
The price is ￥15,093
￥41,608 total
includes taxes & fees
Jan 6 - Jan 7
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Interior
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Condo in Wintergreen Resort

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
2.0 star property
10.0 out of 10, Exceptional, (4)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
The price is ￥15,527
￥37,516 total
includes taxes & fees
Jan 11 - Jan 12
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Condo in Roseland

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (305)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is ￥16,233
￥37,958 total
includes taxes & fees
Jan 6 - Jan 7
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Fridge, microwave, oven, stovetop
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Condo in Wintergreen Resort

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
2.0 star property
9.8 out of 10, Exceptional, (7)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is ￥18,821
￥47,731 total
includes taxes & fees
Jan 6 - Jan 7
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Property grounds
The Modern Mountain Condo

Condo in Wintergreen Resort

The Modern Mountain Condo
10.0 out of 10, Exceptional, (37)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is ￥17,074
￥39,957 total
includes taxes & fees
Jan 13 - Jan 14
The Modern Mountain Condo
Terrace/patio
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Cottage in Nellysford

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
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 ￥29,643
￥72,920 total
includes taxes & fees
Jan 13 - Jan 14
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Pool
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Condo in Roseland

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (143)
"Very clean and pet-friendly "
United States
Heston
The price is ￥19,134
￥41,742 total
includes taxes & fees
Jan 6 - Jan 7
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is ￥36,387
￥72,231 total
includes taxes & fees
Jan 6 - Jan 7
Blackwood Chalet
Interior
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Condo in Roseland

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
9.8 out of 10, Exceptional, (24)
"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 ￥18,821
￥38,398 total
includes taxes & fees
Jan 8 - Jan 9
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Property grounds
Design-Lover’s Getaway • Game Room • Hot Tub

Cabin in Wintergreen Resort

Design-Lover’s Getaway • Game Room • Hot Tub
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 ￥23,526
￥89,474 total
includes taxes & fees
Jan 14 - Jan 15
Design-Lover’s Getaway • Game Room • Hot Tub
Property grounds
Luxury Condo in the Sky! Finest in Wintergreen!

Condo in Wintergreen Resort

Luxury Condo in the Sky! Finest in Wintergreen!
10.0 out of 10, Exceptional, (26)
"Great views"
United States
Arpit N.
Luxury Condo in the Sky! Finest in Wintergreen!
Terrace/patio
Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24

Cabin in Chestnut Springs

Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ￥125,864
￥282,252 total
includes taxes & fees
Jan 6 - Jan 7
Blue Ridge Bliss 9BR/6BA: 2 Homes Across the Street from each other! Sleeps 24
Outdoor spa tub
Bear Tracks Cottage: New Hot Tub + Fire Pit

Cabin in Nellysford

Bear Tracks Cottage: New Hot Tub + Fire Pit
10.0 out of 10, Exceptional, (30)
"Great location. Private and quiet. Great destination for a romantic trip. "
United States
David H.
The price is ￥28,702
￥68,341 total
includes taxes & fees
Jan 13 - Jan 14
Bear Tracks Cottage: New Hot Tub + Fire Pit
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Condo in Wintergreen Resort

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
2.0 star property
10.0 out of 10, Exceptional, (26)
"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 ￥17,645
￥50,817 total
includes taxes & fees
Jan 6 - Jan 7
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Smart TV
Serenity Cabin-Woodland Retreat

Cabin in Wintergreen Resort

Serenity Cabin-Woodland Retreat
10.0 out of 10, Exceptional, (3)
"Great house and great host!"
United States
Joe B.
The price is ￥20,389
￥61,470 total
includes taxes & fees
Jan 6 - Jan 7
Serenity Cabin-Woodland Retreat
Interior
Wintergreen. Sunset Vista Villa - Close to the ski slopes

Condo in Wintergreen Resort

Wintergreen. Sunset Vista Villa - Close to the ski slopes
10.0 out of 10, Exceptional, (95)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is ￥29,015
￥54,602 total
includes taxes & fees
Jan 12 - Jan 13
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Interior
Lofty Pursuits: Spectacular View + EV Charger

Cabin in Treeloft

Lofty Pursuits: Spectacular View + EV Charger
10.0 out of 10, Exceptional, (4)
"Will definitely stay at this location again!!"
United States
Richard W.
The price is ￥26,506
￥61,441 total
includes taxes & fees
Jan 13 - Jan 14
Lofty Pursuits: Spectacular View + EV Charger
Outdoor dining
Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,

Apartment in Wintergreen Resort

Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,
2.0 star property
10.0 out of 10, Exceptional, (1)
"Ski slopes just outside your door! Walk out outside and you are at the top is the slope. Clean, recently updated condo that is well appointed with all you need for a weekend or week long stay. Host was extremely responsive as if on standby if assistance was needed at any time. They were truly invested in making sure i had a great experience. "
United States
Kathleen E.
The price is ￥28,859
￥55,130 total
includes taxes & fees
Jan 6 - Jan 7
Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,
Microwave, oven, stovetop, dishwasher
Overlook 180 degree views w/Peloton!

Condo in Wintergreen Resort

Overlook 180 degree views w/Peloton!
9.4 out of 10, Exceptional, (3)
"Excellent stay. Thank you!"
United States
Kimberly B.
The price is ￥21,958
￥53,947 total
includes taxes & fees
Jan 14 - Jan 15
Overlook 180 degree views w/Peloton!
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

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

10/10 Excellent
"Had all the amenities. View of the mountains and sunrise was amazing."
Dominic Y. 2-night trip
Posted 4 days ago
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

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:

  • View our selection of featured holiday rentals in Wintergreen
  • Use the map to find apartments and other holiday homes in the Wintergreen neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Wintergreen while they last

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 Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop.

How many vacation rentals are there in Wintergreen?

Choose from 230 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.