Photo by Melissa Smestad

Search Vacation Homes in Wintergreen

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
In one month
Dec 26 - Dec 28
In two months
Jan 23 - Jan 25

Vacation Homes in Wintergreen

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 ￥60,067
￥107,105 total
includes taxes & fees
Dec 21 - Dec 22
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Fridge, microwave, oven, stovetop
Spacious + Serene Mtn Top Escape, 4 En Suites

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (47)
"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 ￥22,179
￥68,258 total
includes taxes & fees
Dec 1 - Dec 2
Spacious + Serene Mtn Top Escape, 4 En Suites
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 ￥28,914
￥67,540 total
includes taxes & fees
Dec 10 - Dec 11
"Glass & Pine" Home close to Bold Rock & Vineyards
Terrace/patio
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

Vacation Home in Chestnut Springs

10.0 out of 10, Exceptional, (15)
"We enjoyed the space, amenities and location!"
United States
eric r.
The price is ￥25,085
￥71,348 total
includes taxes & fees
Nov 30 - Dec 1
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
Property grounds
4 BR cabin mins to trails & breweries pets welcome

Vacation Home in Chestnut Springs

9.6 out of 10, Exceptional, (28)
"Nice place and very clean "
United States
Melad K.
The price is ￥30,242
￥91,533 total
includes taxes & fees
Nov 30 - Dec 1
4 BR cabin mins to trails & breweries pets welcome
Exterior
Discounts Avail! Theater Room, Fooseball, Firepit, Mountains!

Vacation Home in Chestnut Springs

9.6 out of 10, Exceptional, (7)
"Great property! Fit our family perfect. Great communication on checkin, house rules and the the house was super clean"
United States
Scott P.
The price is ￥31,102
￥70,029 total
includes taxes & fees
Dec 1 - Dec 2
Discounts Avail! Theater Room, Fooseball, Firepit, Mountains!
Terrace/patio
The Distinguished Squirrel Chalet walking distance

Vacation Home in Treeloft

9.8 out of 10, Exceptional, (7)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The price is ￥32,508
￥71,892 total
includes taxes & fees
Nov 30 - Dec 1
The Distinguished Squirrel Chalet walking distance
Interior
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Vacation Home in Nellysford

10.0 out of 10, Exceptional, (4)
"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 ￥46,887
￥123,211 total
includes taxes & fees
Dec 1 - Dec 2
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Terrace/patio
Beautiful 4-season Mountain Home- New Listing

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (37)
"Great location. Very friendly hosts"
United States
Anthony C.
The price is ￥31,102
￥84,599 total
includes taxes & fees
Dec 1 - Dec 2
Beautiful 4-season Mountain Home- New Listing
Smart TV, fireplace, DVD player, books
5 Min to Ski, Mtn Views, Shuffleboard, Arcade Fun

Vacation Home in Chestnut Springs

2.0 star property
5 Min to Ski, Mtn Views, Shuffleboard, Arcade Fun
Outdoor dining
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!

Vacation Home in Nellysford

9.2 out of 10, Wonderful, (52)
"Great stay with plenty of room"
United States
Christopher C.
The price is ￥46,731
￥116,211 total
includes taxes & fees
Dec 1 - Dec 2
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!
Exterior
Mountain Inn Studio 91 with Wintergreen Advantage

Vacation Home in Wintergreen

The price is ￥24,850
￥42,273 total
includes taxes & fees
Dec 10 - Dec 11
Mountain Inn Studio 91 with Wintergreen Advantage
Terrace/patio
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Vacation Home in Laurel Ridge

10.0 out of 10, Exceptional, (2)
"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 ￥46,106
￥141,113 total
includes taxes & fees
Dec 2 - Dec 3
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds
Smart TV, fireplace, video games, DVD player
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Vacation Home in Pedlars Edge

9.8 out of 10, Exceptional, (33)
"Well stocked fun house! Kind owners, views for days, comfy beds. We enjoyed a fun-filled weekend in the summer, cooked, played games. It was a dream vacay. Please note that there are limitations on resort amenities, but we went to Lake Sherando and had a great time."
United States
newsha d.
The price is ￥51,884
￥112,304 total
includes taxes & fees
Nov 30 - Dec 1
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Terrace/patio
Stunning Views, Hot Tub, Impeccable Design

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (13)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
Stunning Views, Hot Tub, Impeccable Design
Outdoor dining
Red White & WTG: Game Room + Hot Tub

Vacation Home in Pedlars Edge

10.0 out of 10, Exceptional, (3)
"Very clean, check in was so easy and so was checkout! Very close to the slopes. Will stay here again."
United States
Taylor
The price is ￥70,174
￥160,244 total
includes taxes & fees
Dec 1 - Dec 2
Red White & WTG: Game Room + Hot Tub
Terrace/patio
Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Vacation Home in Wintergreen Resort

Hilltop Hideaway - Wintergreen 5BR with Hot Tub
Outdoor dining
Mountain Views in Wintergreen

Vacation Home in Laurel Ridge

10.0 out of 10, Exceptional, (9)
"We had a great trip! The house was beautiful with so much space! We loved using the hot tub at night. The host was helpful and responsive to all my questions. Would be happy to book this house again."
United States
Kara S.
The price is ￥82,052
￥153,400 total
includes taxes & fees
Dec 28 - Dec 29
Mountain Views in Wintergreen
Outdoor spa tub
Serene Wintergreen Retreat, Nestled in the Trees

Vacation Home in Wintergreen Resort

9.8 out of 10, Exceptional, (17)
"The property is as wonderful as it looks in the photos. Very close to a beautiful waterfall trail. Definitely would stay here again in a different season to take it all in again."
United States
Brandon D.
The price is ￥106,668
￥181,922 total
includes taxes & fees
Dec 29 - Dec 30
Serene Wintergreen Retreat, Nestled in the Trees
Indoor spa tub
Upscale and Family-Friendly in Wintergreen

Vacation Home in Roseland

9.6 out of 10, Exceptional, (26)
"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 ￥82,052
￥158,990 total
includes taxes & fees
Dec 21 - Dec 22
Upscale and Family-Friendly in Wintergreen
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

Wintergreen. Sunset Vista Villa - Sea of Mountains

Wintergreen. Sunset Vista Villa - Sea of Mountains

10/10 Excellent
"Comfortable condo, nice view, easy instructions and clear responsive communication. Seasonal decorations were a nice bonus. We will be returning. "
William W. 1-night trip
Posted 4 days ago
Wintergreen. Sunset Vista Villa - Sea of Mountains

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
314
Accommodation
414 Vacation Homes
Lowest Price
￥42,273
Highest Price
￥181,922

Explore a world of travel with Expedia