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Search Vacation Homes in Wintergreen

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Our top choices for Wintergreen vacation homes

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"Amazing place, clean and quiet even though there are houses nearby. Hosts were excellent with communication!"
United States
Courtney S.
The price is AED 397
AED 1,200 total
includes taxes & fees
11 Dec - 12 Dec
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort
10.0 out of 10, Exceptional, (48)
"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 AED 528
AED 1,600 total
includes taxes & fees
11 Dec - 12 Dec
Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen 5BR with Hot Tub, Sauna, Firepit

Chestnut Springs
10.0 out of 10, Exceptional, (4)
"Loved that everything was provided! We were very appreciative of the shampoo, soap, body wash, paper towels and toilet paper provided. It was all good quality and sufficient for our entire stay. We had a great stay!"
United States
Lisa R.
Wintergreen 5BR with Hot Tub, Sauna, Firepit

"Glass & Pine" Home close to Bold Rock & Vineyards

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 AED 679
AED 1,567 total
includes taxes & fees
15 Dec - 16 Dec
"Glass & Pine" Home close to Bold Rock & Vineyards

Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

Chestnut Springs
10.0 out of 10, Exceptional, (15)
"Great stay!"
United States
Cheryl P.
The price is AED 589
AED 1,677 total
includes taxes & fees
14 Dec - 15 Dec
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

4 BR cabin mins to trails & breweries pets welcome

Chestnut Springs
9.6 out of 10, Exceptional, (28)
"Nice place and very clean "
United States
Melad K.
The price is AED 711
AED 2,151 total
includes taxes & fees
11 Dec - 12 Dec
4 BR cabin mins to trails & breweries pets welcome

The Distinguished Squirrel Chalet walking distance

Treeloft
9.0 out of 10, Wonderful, (8)
"we appreciated that it was stocked with basic spices, coffee, necessary cookware, etc. Nice location "
United States
Ryan R.
The Distinguished Squirrel Chalet walking distance

Beautiful 4-season Mountain Home- New Listing

Wintergreen Resort
10.0 out of 10, Exceptional, (38)
"Great location. Very friendly hosts"
United States
Anthony C.
The price is AED 731
AED 1,972 total
includes taxes & fees
15 Dec - 16 Dec
Beautiful 4-season Mountain Home- New Listing

Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

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 AED 1,102
AED 2,887 total
includes taxes & fees
11 Dec - 12 Dec
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

Mountain Inn Studio 91 with Wintergreen Advantage

Wintergreen
Mountain Inn Studio 91 with Wintergreen Advantage

2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

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 AED 1,200
AED 3,468 total
includes taxes & fees
11 Dec - 12 Dec
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

Adventure Awaits

Laurel Ridge
9.2 out of 10, Wonderful, (7)
"our stay was so fun! "
United States
Kaden C.
The price is AED 1,120
AED 2,220 total
includes taxes & fees
5 Jan - 6 January 2026
Adventure Awaits

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

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.
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Stunning Views, Hot Tub, Impeccable Design

Wintergreen Resort
10.0 out of 10, Exceptional, (14)
"This house is beautiful, well kept, and is in a great location near hikes and breweries!"
United States
Lauren M.
The price is AED 1,388
AED 3,003 total
includes taxes & fees
22 Dec - 23 Dec
Stunning Views, Hot Tub, Impeccable Design

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Wintergreen Resort
The price is AED 1,735
AED 3,545 total
includes taxes & fees
17 Dec - 18 Dec
Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Red White & WTG: Game Room + Hot Tub

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
Red White & WTG: Game Room + Hot Tub

Mountain Views, Hot Tub, Impeccable Design

Wintergreen Resort
9.2 out of 10, Wonderful, (5)
"An amazing view of the valley, the home was gorgeous, well stocked with essential items and more. The beds were very comfortable, the whole house had a comfy, welcoming atmosphere. The adventures we went on were within 30 minutes of the house.We had a wonderful time there!"
United States
Sid V.
Mountain Views, Hot Tub, Impeccable Design

Serene Wintergreen Retreat, Nestled in the Trees

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 AED 2,507
AED 4,275 total
includes taxes & fees
29 Dec - 30 Dec
Serene Wintergreen Retreat, Nestled in the Trees

Ridge Retreat @ Wintergreen!

Wintergreen Resort
9.6 out of 10, Exceptional, (5)
"Beautiful home and it has everything you need for a get-a-way. Five couples and plenty of room to have your own space. Close to lots of recreation and entertainment. "
United States
Robert J.
The price is AED 2,795
AED 5,144 total
includes taxes & fees
2 Jan - 3 January 2026
Ridge Retreat @ Wintergreen!

Upscale and Family-Friendly in Wintergreen

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 AED 1,735
AED 3,403 total
includes taxes & fees
21 Dec - 22 Dec
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.
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Top Wintergreen Hotel Reviews