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Search Vacation Homes in Wintergreen

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Vacation Homes in Wintergreen

Property grounds
4 BR cabin mins to trails & breweries pets welcome

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 SAR 726
SAR 2,198 total
includes taxes & fees
5 Dec - 6 Dec
4 BR cabin mins to trails & breweries pets welcome
Outdoor spa tub
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, (24)
"A wonderful property to see mountain views and visit the surrounding area."
United States
Peggy B.
The price is SAR 450
SAR 1,302 total
includes taxes & fees
11 Dec - 12 Dec
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!
Dining
"Glass & Pine" Home close to Bold Rock & Vineyards

"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 SAR 694
SAR 1,622 total
includes taxes & fees
8 Dec - 9 Dec
"Glass & Pine" Home close to Bold Rock & Vineyards
Terrace/patio
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking

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 SAR 602
SAR 1,714 total
includes taxes & fees
7 Dec - 8 Dec
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
Exterior
Discounts Avail! Theater Room, Fooseball, Firepit, Mountains!

Discounts Avail! Theater Room, Fooseball, Firepit, Mountains!

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 SAR 747
SAR 1,695 total
includes taxes & fees
8 Dec - 9 Dec
Discounts Avail! Theater Room, Fooseball, Firepit, Mountains!
Terrace/patio
The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance

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 SAR 732
SAR 1,678 total
includes taxes & fees
8 Dec - 9 Dec
The Distinguished Squirrel Chalet walking distance
Terrace/patio
Beautiful 4-season Mountain Home- New Listing

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.
Beautiful 4-season Mountain Home- New Listing
Terrace/patio
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds

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 SAR 1,107
SAR 3,389 total
includes taxes & fees
8 Dec - 9 Dec
2 Mins to Slopes: HotTub, Game room, Family & Pets, 3 King Beds
Exterior
Mountain Inn Studio 91 with Wintergreen Advantage

Mountain Inn Studio 91 with Wintergreen Advantage

Wintergreen
The price is SAR 597
SAR 1,015 total
includes taxes & fees
17 Dec - 18 Dec
Mountain Inn Studio 91 with Wintergreen Advantage
Interior
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

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 SAR 1,126
SAR 2,951 total
includes taxes & fees
7 Dec - 8 Dec
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Outdoor dining
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!

Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!

Nellysford
9.2 out of 10, Wonderful, (52)
"Great stay with plenty of room"
United States
Christopher C.
The price is SAR 1,066
SAR 2,703 total
includes taxes & fees
7 Dec - 8 Dec
Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!
Fridge, microwave, oven, stovetop
Spacious + Serene Mtn Top Escape, 4 En Suites

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.
Spacious + Serene Mtn Top Escape, 4 En Suites
Smart TV, fireplace, video games, DVD player
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

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.
The price is SAR 1,247
SAR 2,698 total
includes taxes & fees
7 Dec - 8 Dec
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Terrace/patio
Stunning Views, Hot Tub, Impeccable Design

Stunning Views, Hot Tub, Impeccable Design

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
Terrace/patio
Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Wintergreen Resort
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
Outdoor spa tub
Mountain Views, Hot Tub, Impeccable Design

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
Outdoor dining
Mountain Views in Wintergreen

Mountain Views in Wintergreen

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 SAR 1,971
SAR 3,731 total
includes taxes & fees
28 Dec - 29 Dec
Mountain Views in Wintergreen
Outdoor spa tub
Serene Wintergreen Retreat, Nestled in the Trees

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.
Serene Wintergreen Retreat, Nestled in the Trees
TV, fireplace
Ridge Retreat @ Wintergreen!

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.
Ridge Retreat @ Wintergreen!
Indoor spa tub
Upscale and Family-Friendly in 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.
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

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10/10 Excellent
"Perfect stay yet again! "
Ashton B. 3-night trip
Posted 2 days ago
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes