Photo by Melissa Smestad

Wintergreen Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Jan 6 - Jan 7
Tomorrow
Jan 7 - Jan 8
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

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.
$265 nightly
The price is $279
Jan 11 - Jan 12
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
Fridge, microwave, oven, stovetop
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
Stylish-Updated-Central -Walk to Slopes-Dogs OK!
Property grounds
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.
$202 nightly
The price is $227
Jan 11 - Jan 12
Total with taxes and fees
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.
$216 nightly
The price is $242
Jan 11 - Jan 12
Total with taxes and fees
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.
$271 nightly
The price is $304
Jan 7 - Jan 8
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Fireplace
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.
$224 nightly
The price is $251
Jan 13 - Jan 14
Total with taxes and fees
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.
$414 nightly
The price is $465
Jan 13 - Jan 14
Total with taxes and fees
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Property grounds
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
$234 nightly
The price is $263
Jan 7 - Jan 8
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Cabin, Private Bathroom (Blackwood Chalet) | Lounge
Blackwood Chalet

Cabin in Nellysford

Blackwood Chalet
2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
$388 nightly
The price is $411
Jan 12 - Jan 13
Total with taxes and fees
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.
$218 nightly
The price is $245
Jan 8 - Jan 9
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Interior
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.
$508 nightly
The price is $570
Jan 7 - Jan 8
Total with taxes and fees
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)
"Amazing place with even more amazing views. Very comfortable and beautiful place. We had high expectations based on the pictures in the listing, and the place exceeded these high expectations. Fantastic place."
United States
missy s.
Luxury Condo in the Sky! Finest in Wintergreen!
Outdoor dining
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)
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)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
$410 nightly
The price is $436
Jan 13 - Jan 14
Total with taxes and fees
Bear Tracks Cottage: New Hot Tub + Fire Pit
Fridge, microwave, oven, stovetop
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.
$286 nightly
The price is $321
Jan 7 - Jan 8
Total with taxes and fees
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.
$322 nightly
The price is $362
Jan 7 - Jan 8
Total with taxes and fees
Serenity Cabin-Woodland Retreat
Exterior
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.
$290 nightly
The price is $325
Jan 12 - Jan 13
Total with taxes and fees
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.
$366 nightly
The price is $390
Jan 14 - Jan 15
Total with taxes and fees
Lofty Pursuits: Spectacular View + EV Charger
Exterior detail
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.
Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,
Outdoor dining
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.
$297 nightly
The price is $340
Jan 11 - Jan 12
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 1 day ago
"SERENITY 4 ALL SEASONS"

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation 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 low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $242 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.