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Vacation Homes in Wintergreen

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.
$295 nightly
The price is $331
Dec 3 - Dec 4
Total with taxes and fees
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.
$372 nightly
The price is $427
Nov 30 - Dec 1
Total with taxes and fees
"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)
"We enjoyed the space, amenities and location!"
United States
eric r.
$407 nightly
The price is $457
Nov 30 - Dec 1
Total with taxes and fees
Cabin Ski Retreat • 5 Min to Slopes • Hot Tub • Firepit • Game Room • Hiking
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.
$389 nightly
The price is $446
Dec 2 - Dec 3
Total with taxes and fees
The Distinguished Squirrel Chalet walking distance
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.
$522 nightly
The price is $586
Nov 30 - Dec 1
Total with taxes and fees
4 BR cabin mins to trails & breweries pets welcome
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, (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.
$389 nightly
The price is $437
Dec 1 - Dec 2
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Terrace/patio
Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing

Wintergreen Resort
10.0 out of 10, Exceptional, (37)
"Great location. Very friendly hosts"
United States
Anthony C.
$482 nightly
The price is $541
Dec 1 - Dec 2
Total with taxes and fees
Beautiful 4-season Mountain Home- New Listing
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.
$702 nightly
The price is $788
Dec 1 - Dec 2
Total with taxes and fees
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!
Exterior
Mountain Inn Studio 91 with Wintergreen Advantage

Mountain Inn Studio 91 with Wintergreen Advantage

Wintergreen
$241 nightly
The price is $270
Nov 30 - Dec 1
Total with taxes and fees
Mountain Inn Studio 91 with Wintergreen Advantage
Terrace/patio
Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Wintergreen Resort
$920 nightly
The price is $1,033
Dec 17 - Dec 18
Total with taxes and fees
Hilltop Hideaway - Wintergreen 5BR with Hot Tub
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.
$728 nightly
The price is $818
Dec 22 - Dec 23
Total with taxes and fees
Serene Wintergreen Retreat, Nestled in the Trees
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.
$804 nightly
The price is $903
Dec 2 - Dec 3
Total with taxes and fees
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.

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.
$640 nightly
The price is $719
Nov 30 - Dec 1
Total with taxes and fees
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.
$784 nightly
The price is $880
Dec 22 - Dec 23
Total with taxes and fees
Stunning Views, Hot Tub, Impeccable Design
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.
$914 nightly
The price is $1,017
Dec 21 - Dec 22
Total with taxes and fees
Upscale and Family-Friendly in Wintergreen
Fridge, microwave, oven, stovetop
Whole House

Whole House

Amherst
9.8 out of 10, Exceptional, (31)
"The property was just what we wanted -- quiet, private, spacious, comfortable, well equipped. Easy to find and everything worked! We will definitely aim to book this property again when we're back in the area."
United States
Andrew
$124 nightly
The price is $137
Nov 29 - Nov 30
Total with taxes and fees
Whole House
Interior
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Waynesboro
10.0 out of 10, Exceptional, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
$150 nightly
The price is $166
Dec 21 - Dec 22
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Outdoor dining
Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
Nellysford
$260 nightly
The price is $292
Nov 30 - Dec 1
Total with taxes and fees
Tucked Inn: Lower Unit - NEW Nelson Co Getaway
Exterior
The Firefly Springhouse

The Firefly Springhouse

Staunton
9.8 out of 10, Exceptional, (43)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
$103 nightly
The price is $114
Dec 1 - Dec 2
Total with taxes and fees
The Firefly Springhouse
Smart TV
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Waynesboro
9.6 out of 10, Exceptional, (44)
"We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. "
United States
Virginia W.
$183 nightly
The price is $204
Nov 30 - Dec 1
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!
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. 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 3 days ago
Wintergreen. Sunset Vista Villa - Sea of Mountains

Find out more about Wintergreen

Wintergreen Vacation Homes information

Number of reviews
378
Accommodation
414 Vacation Homes
Lowest Price
$114
Highest Price
$1,033

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