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Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Wintergreen

Cabin, Private Bathroom (Blackwood Chalet) | Exterior
Blackwood Chalet

Cabin in Nellysford

2.0 star property
10.0 out of 10, Exceptional, (3)
"Love the area"
United States
Toni
The price is ￥26,285
￥60,624 total
includes taxes & fees
Nov 23 - Nov 24
Blackwood Chalet
Interior
Wintergreen. Sunset Vista Villa - Sea of Mountains

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (90)
"Another great stay at Sunset Vista! Clean, comfortable, convenient, well stocked, great views, amazing host - what more could we ask for? We will be back!"
United States
Judy C.
The price is ￥18,197
￥40,870 total
includes taxes & fees
Nov 23 - Nov 24
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Condo in Wintergreen Resort

2.0 star property
10.0 out of 10, Exceptional, (24)
"Excellent stay! Easy check in, Paul was super responsive and gave all the information we needed up front. Perfect for our overnight get away! Would absolutely stay again."
United States
Taylor H.
The price is ￥13,974
￥45,335 total
includes taxes & fees
Nov 20 - Nov 21
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Property grounds
The Modern Mountain Condo

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (31)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
The price is ￥15,546
￥37,337 total
includes taxes & fees
Nov 22 - Nov 23
The Modern Mountain Condo
Terrace/patio
Wintergreen Condo -Steps to Ski and restaurants

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (29)
"Had everything we needed, snacks and coffee were great for a cold weekend."
United States
Michael L.
The price is ￥17,701
￥41,151 total
includes taxes & fees
Nov 20 - Nov 21
Wintergreen Condo -Steps to Ski and restaurants
Outdoor dining
Escape to the Blue Ridge Mountains at Wine-tergreen!

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (122)
"The condo was very nice. Located on top of the mountain resort having spectacular views for the outlook just a short walk away. We will be boocking again for our next trip. "
United States
John
The price is ￥16,629
￥38,378 total
includes taxes & fees
Nov 25 - Nov 26
Escape to the Blue Ridge Mountains at Wine-tergreen!
Exterior
Laurelwood Hollow: Walk to Ski & Swim

Apartment in 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 ￥14,775
￥43,416 total
includes taxes & fees
Nov 20 - Nov 21
Laurelwood Hollow: Walk to Ski & Swim
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Condo in Roseland

9.0 out of 10, Wonderful, (298)
"Great view!!"
United States
Suzanne W.
The price is ￥15,397
￥36,678 total
includes taxes & fees
Dec 1 - Dec 2
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Pool
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Condo in Roseland

9.6 out of 10, Exceptional, (140)
"Great stay in Wintergreen!"
United States
Pete K.
The price is ￥18,975
￥41,395 total
includes taxes & fees
Dec 12 - Dec 13
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Terrace/patio
Pine Cottage: Hot Tub, 2 mins to Bold Rock!

Cottage in Nellysford

10.0 out of 10, Exceptional, (22)
"The house was super cute and accommodated our whole group. It was close to a good amount of breweries and wineries. "
United States
Claire B.
The price is ￥29,346
￥71,666 total
includes taxes & fees
Nov 23 - Nov 24
Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Smart TV
Serenity Cabin-Woodland Retreat

Cabin in Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"Amazing stay at Serenity! Beautiful well appointed home. House was clean, warm and inviting. Communication with host was wonderful! A definite recommendation for a peaceful stay up in Wintergreen. "
United States
Judy E.
The price is ￥17,108
￥56,939 total
includes taxes & fees
Nov 20 - Nov 21
Serenity Cabin-Woodland Retreat
Interior
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Condo in Roseland

9.8 out of 10, Exceptional, (19)
"Excellent throughout"
United States
katherine
The price is ￥18,632
￥39,058 total
includes taxes & fees
Nov 29 - Nov 30
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Property grounds
Ready for Ski Season! Book NOW!

Apartment in Wintergreen Resort

9.8 out of 10, Exceptional, (25)
"Love everything about our stay there "
United States
Natalia S.
The price is ￥24,067
￥49,753 total
includes taxes & fees
Nov 20 - Nov 21
Ready for Ski Season! Book NOW!
Outdoor spa tub
Bear Tracks Cottage: New Hot Tub + Fire Pit

Cabin in Nellysford

10.0 out of 10, Exceptional, (28)
"Great for taking advantage of all Nelson County's attractions. "
United States
Darrell D.
The price is ￥28,414
￥67,655 total
includes taxes & fees
Dec 1 - Dec 2
Bear Tracks Cottage: New Hot Tub + Fire Pit
Outdoor dining
Golf Course Views • 3 King Suites • Fireplace • EV Charger

Apartment in Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"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.
Golf Course Views • 3 King Suites • Fireplace • EV Charger
Exterior
Mountain Inn Studio 96 with Wintergreen Advantage

Condo in Wintergreen

10.0 out of 10, Exceptional, (1)
"A wonderful condo at Wintergreen! It was great to snowboard the whole day and the next day. This was a lovely and clean place to rest. "
United States
Lana
The price is ￥24,688
￥41,997 total
includes taxes & fees
Nov 21 - Nov 22
Mountain Inn Studio 96 with Wintergreen Advantage
Outdoor spa tub
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (24)
"A wonderful property to see mountain views and visit the surrounding area."
United States
Peggy B.
The price is ￥16,797
￥51,524 total
includes taxes & fees
Nov 24 - Nov 25
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Property grounds
Luxury Condo in the Sky! Finest in Wintergreen!

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (26)
"Great views"
United States
Arpit N.
Luxury Condo in the Sky! Finest in Wintergreen!
Dining
"Glass & Pine" Home close to Bold Rock & Vineyards

Vacation Home in 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 ￥28,773
￥66,337 total
includes taxes & fees
Nov 24 - Nov 25
"Glass & Pine" Home close to Bold Rock & Vineyards
Terrace/patio
Cozy Cute Condo in Wintergreen Resort

Condo in Roseland

10.0 out of 10, Exceptional, (2)
"Great Location!"
United States
Thomas W.
The price is ￥24,533
￥51,090 total
includes taxes & fees
Nov 20 - Nov 21
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

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

10/10 Excellent
"Very cozy home. Clean and comfortable. Wonderful area for a Fall getaway. "
Darlene V. 3-night trip
Posted 5 days ago
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall

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?

Luxury Wintergreen 5BR • Hot Tub • Sleeps 16+ • Dog Friendly: 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 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Large and Luxurious Exec 5BR Chalet and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many vacation rentals are there in Wintergreen?

Choose from 225 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.