Wintergreen Vacation Rentals

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Our top choices for Wintergreen vacation rentals

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (5 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 CA $130
CA $382 total
includes taxes & fees
Mar 2 - Mar 3
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, (6 reviews)
"We loved the 'ski-in/ski-out' convenience. Cute condo with everything you need for your stay. The water and snacks were a nice gesture. "
United States
Esperanza
The price is CA $123
CA $313 total
includes taxes & fees
Mar 3 - Mar 4
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, (41 reviews)
"Quiet, one-night stay while in the area for an event. "
United States
Julie M.
The price is CA $143
CA $339 total
includes taxes & fees
Mar 5 - Mar 6
The Modern Mountain Condo

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

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.8 out of 10, Exceptional, (8 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
The price is CA $164
CA $422 total
includes taxes & fees
Feb 24 - Feb 25
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

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, (99 reviews)
"Fantastic stay again! Condo is perfect for a get away! "
United States
Jenna M.
The price is CA $219
CA $439 total
includes taxes & fees
Feb 11 - Feb 12
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, (24 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 CA $336
CA $739 total
includes taxes & fees
Feb 24 - Feb 25
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Wintergreen Resort Condo Available Now!!

Wintergreen Resort Condo Available Now!!
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.
The price is CA $212
CA $444 total
includes taxes & fees
Feb 11 - Feb 12
Wintergreen Resort Condo Available Now!!

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, (124 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
The price is CA $176
CA $376 total
includes taxes & fees
Mar 1 - Mar 2
Escape to the Blue Ridge Mountains at Wine-tergreen!

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, (26 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 CA $164
CA $344 total
includes taxes & fees
Feb 11 - Feb 12
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Little Mountain Haven. True ski-in, ski-out. First floor!

Little Mountain Haven. True ski-in, ski-out. First floor!
Wintergreen Resort
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $82
CA $261 total
includes taxes & fees
Mar 9 - Mar 10
Little Mountain Haven. True 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, (145 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $167
CA $364 total
includes taxes & fees
Feb 11 - Feb 12
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-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, (26 reviews)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is CA $198
CA $517 total
includes taxes & fees
Mar 3 - Mar 4
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

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, (43 reviews)
"Cute little place. Well stocked, easy access, and very convenient to wintergreen facilities. "
United States
david
The price is CA $167
CA $380 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

"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 CA $237
CA $566 total
includes taxes & fees
Mar 3 - Mar 4
"Glass & Pine" Home close to Bold Rock & Vineyards

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, (311 reviews)
"Outstanding views from the deck!! Loved it!"
United States
Kerry M.
The price is CA $142
CA $348 total
includes taxes & fees
Feb 11 - Feb 12
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (31 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 CA $198
CA $501 total
includes taxes & fees
Feb 9 - Feb 10
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (36 reviews)
"Very clean, well organized, excellent views"
United States
Guy M.
The price is CA $190
CA $398 total
includes taxes & fees
Mar 2 - Mar 3
Panoramic Peak: Wintergreen Condo with Views

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 CA $178
CA $455 total
includes taxes & fees
Mar 10 - Mar 11
Overlook 180 degree views w/Peloton!

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (31 reviews)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
The price is CA $250
CA $594 total
includes taxes & fees
Mar 3 - Mar 4
Bear Tracks Cottage: New Hot Tub + Fire Pit

Cozy Cute Condo in Wintergreen Resort

Cozy Cute Condo in Wintergreen Resort
Roseland
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed it so much! So cozy and close to the resort! "
United States
Katie B.
The price is CA $216
CA $450 total
includes taxes & fees
Feb 9 - Feb 10
Cozy Cute Condo in Wintergreen Resort
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Wintergreen. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

4 BR cabin mins to trails & breweries pets welcome: Visitors give good reviews to this Wintergreen vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 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 Mountain Views in Wintergreen and One of the Best Views in Wintergreen!.

How many vacation rentals are there in Wintergreen?

Choose from 228 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.