Search Vacation Homes in Wintergreen

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Wintergreen vacation homes

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 ¥27,406
¥64,951 total
includes taxes & fees
Jan 21 - Jan 22
"Glass & Pine" Home close to Bold Rock & Vineyards

Vacation Home in Wintergreen Resort

Beautiful 4-season Mountain Home- New Listing
10.0 out of 10, Exceptional, (39 reviews)
"The property is clean, bed rooms are spacious. 3.5 bath, kitchen has latest appliances, bedding & accessories are star hotel standard. We loved our stay. "
United States
Mridul G.
The price is ¥31,480
¥84,917 total
includes taxes & fees
Jan 21 - Jan 22
Beautiful 4-season Mountain Home- New Listing
10.0 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Cheryl P.
The price is ¥29,283
¥77,120 total
includes taxes & fees
Feb 9 - Feb 10
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
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 ¥26,652
¥64,747 total
includes taxes & fees
Feb 1 - Feb 2
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Vacation Home in Wintergreen Resort

Spacious + Serene Mtn Top Escape, 4 En Suites
10.0 out of 10, Exceptional, (50 reviews)
"Amazing stay for nelson 151 trip for Birthday. Owners are amazing communication was easy and quick. Property is beautiful and very well maintained. We will be staying here again. "
United States
DANIEL H.
The price is ¥17,376
¥62,149 total
includes taxes & fees
Jan 21 - Jan 22
Spacious + Serene Mtn Top Escape, 4 En Suites
9.0 out of 10, Wonderful, (8 reviews)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The price is ¥32,375
¥73,864 total
includes taxes & fees
Jan 21 - Jan 22
The Distinguished Squirrel Chalet walking distance
10.0 out of 10, Exceptional, (10 reviews)
"House had everything we could possibly want. The layout was perfect for teens to have their own space."
United States
Jessica S.
The price is ¥45,677
¥109,897 total
includes taxes & fees
Jan 21 - Jan 22
Whiskey Ridge - Luxury Mountaintop Family Retreat * Dog Friendly * Hot Tub
10.0 out of 10, Exceptional, (5 reviews)
"We really enjoyed our stay! The home was amazing and very well appointed. We enjoyed local breweries and hiking!"
United States
Rachel F.
The price is ¥47,457
¥124,709 total
includes taxes & fees
Jan 21 - Jan 22
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
9.6 out of 10, Exceptional, (29 reviews)
"Nice place and very clean "
United States
Melad K.
The price is ¥42,711
¥108,365 total
includes taxes & fees
Jan 21 - Jan 22
4 BR cabin mins to trails & breweries pets welcome

Vacation Home in Pedlars Edge

Family-Friendly Meets Luxury
9.8 out of 10, Exceptional, (7 reviews)
"Great Spot for Family gathering"
United States
Ary S.
The price is ¥112,117
¥212,599 total
includes taxes & fees
Jan 22 - Jan 23
Family-Friendly Meets Luxury
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful house and host! "
United States
Alyshia F.
The price is ¥83,050
¥179,247 total
includes taxes & fees
Feb 15 - Feb 16
​Luxury Oasis! Family&Pets, Outdoor-Lounge, F​ire pit, Hot tub
10.0 out of 10, Exceptional, (3 reviews)
"We had such a great time, the cabin was great for our friends weekend with perfect sleeping accommodations for a big group. The deck was fantastic for dinner and s’mores bar!"
United States
Josh B.
The price is ¥58,605
¥156,768 total
includes taxes & fees
Jan 21 - Jan 22
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds
10.0 out of 10, Exceptional, (15 reviews)
"The house was very clean and a great location for eats and drinks. "
United States
Erin D.
The price is ¥68,734
¥143,985 total
includes taxes & fees
Jan 27 - Jan 28
Family Fun Escape: Hot Tub, Gameroom, Fireplace, Dog Friendly, Firepits & Grill
10.0 out of 10, Exceptional, (68 reviews)
"Loved our stay - the house, location, and amenities were perfect for us!"
United States
Alex & Kathy N.
The price is ¥71,186
¥121,867 total
includes taxes & fees
Feb 5 - Feb 6
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Vacation Home in Pedlars Edge

Red White & WTG: Game Room + Hot Tub
10.0 out of 10, Exceptional, (4 reviews)
"I liked the following: -spacious house -supplies on hand -cleanliness of the house -location -quietness -# of bathrooms and bedrooms -no pets rule -no smoking rule -house decor"
United States
Deran
The price is ¥70,996
¥160,524 total
includes taxes & fees
Jan 21 - Jan 22
Red White & WTG: Game Room + Hot Tub

Vacation Home in Wintergreen Resort

Mountain Views, Hot Tub, Impeccable Design
9.2 out of 10, Wonderful, (5 reviews)
"Lovely house with a great view! Highly recommend!"
United States
Ron S.
Mountain Views, Hot Tub, Impeccable Design
9.6 out of 10, Exceptional, (28 reviews)
"Well appointed house and property, lots of space, all amenities included. Comms with host were timely and responsive."
United States
Tammy G.
The price is ¥74,745
¥156,611 total
includes taxes & fees
Feb 1 - Feb 2
Upscale and Family-Friendly in Wintergreen
9.6 out of 10, Exceptional, (45 reviews)
"loved the quiet location, sunny private back yard, and well-stocked kitchen"
United States
George D.
The price is ¥18,508
¥32,220 total
includes taxes & fees
Jan 21 - Jan 22
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
10.0 out of 10, Exceptional, (32 reviews)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
The price is ¥28,316
¥65,908 total
includes taxes & fees
Jan 21 - Jan 22
Hillside Haven: Modern Retreat, Mountain Views

Vacation Home in Staunton

The Firefly Springhouse
9.8 out of 10, Exceptional, (48 reviews)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
The price is ¥13,092
¥18,092 total
includes taxes & fees
Jan 31 - Feb 1
The Firefly Springhouse
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Wintergreen Hotel Reviews

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
432
Accommodation
197 Vacation Homes
Lowest Price
¥18,092
Highest Price
¥212,599

Explore a world of travel with Expedia