A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Our top choices for Wintergreen vacation homes

Art & Soul

Art & Soul
2.0 star property
Nellysford
The price is AED 2,277
AED 2,557 total
includes taxes & fees
21 Jul - 22 Jul
Art & Soul

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"Great place"
United States
Stephen M.
The price is AED 353
AED 1,379 total
includes taxes & fees
5 Jul - 6 Jul
Spacious + Serene Mtn Top Escape, 4 En Suites

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

"Glass & Pine" Home close to Bold Rock & Vineyards
Nellysford
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 AED 617
AED 1,422 total
includes taxes & fees
5 Jul - 6 Jul
"Glass & Pine" Home close to Bold Rock & Vineyards

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (32 reviews)
"Everything was amazing I couldn't recommend this property enough"
United States
Stanley W.
The price is AED 567
AED 1,433 total
includes taxes & fees
27 Jul - 28 Jul
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Beautiful 4-season Mountain Home- New Listing

Beautiful 4-season Mountain Home- New Listing
Wintergreen Resort
10.0 out of 10, Exceptional, (44 reviews)
"We had a great time staying here! The place was in great condition and in such a great location! The host was very responsive and helpful with all questions. I would absolutely recommend and will certainly try to book here again in the future!"
United States
Chad H.
The price is AED 731
AED 1,980 total
includes taxes & fees
6 Jul - 7 Jul
Beautiful 4-season Mountain Home- New Listing

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, (35 reviews)
"We really enjoyed our stay in Wintergreen! The location was great and the view was incredible. The house was spotless and we loved that there was a full kitchen. We recommend to others! "
United States
Laura J.
The price is AED 900
AED 2,413 total
includes taxes & fees
3 Aug - 4 Aug
4 BR cabin mins to trails & breweries pets welcome

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds
Laurel Ridge
10.0 out of 10, Exceptional, (5 reviews)
"Fabulous house and we all had a great time! "
United States
Mindy M.
The price is AED 1,215
AED 3,489 total
includes taxes & fees
6 Jul - 7 Jul
Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

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, (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 AED 1,311
AED 3,193 total
includes taxes & fees
13 Jul - 14 Jul
Modern 5 bedroom retreat w/ mountain views. Sauna + Wood fired pizza oven!

The Distinguished Squirrel Chalet walking distance

The Distinguished Squirrel Chalet walking distance
Treeloft
9.2 out of 10, Wonderful, (13 reviews)
"Great location and the slopes are easily accessible!"
United States
Mark H.
The price is AED 995
AED 1,967 total
includes taxes & fees
28 Jul - 29 Jul
The Distinguished Squirrel Chalet walking distance

​Luxury Oasis w/outdoor lounge! Hiking, lakes, brew trails & golf. Pet friendly!

​Luxury Oasis w/outdoor lounge! Hiking, lakes, brew trails & golf. Pet friendly!
Chestnut Springs
10.0 out of 10, Exceptional, (9 reviews)
"We truly enjoyed our stay, the host Ashley was very accommodating and responsive to any questions we had. Would highly recommended. "
United States
Anonymous traveler
​Luxury Oasis w/outdoor lounge! Hiking, lakes, brew trails & golf. Pet friendly!

Mountain Mindset

Mountain Mindset
2.0 star property
Laurel Ridge
The price is AED 1,227
AED 2,203 total
includes taxes & fees
7 Jul - 8 Jul
Mountain Mindset

Family-Friendly Meets Luxury

Family-Friendly Meets Luxury
Pedlars Edge
9.8 out of 10, Exceptional, (8 reviews)
"Great Spot for Family gathering"
United States
Ary S.
Family-Friendly Meets Luxury

7th Hole Chalet - Summer Getaway w Hot Tub, Sauna

7th Hole Chalet - Summer Getaway w Hot Tub, Sauna
Wintergreen Resort
8.0 out of 10, Very Good, (1 review)
"We enjoyed our stay at the 7th hole chalet and would return. The house is spacious and was clean and included everything we needed. It did seem to have a lot of extra, unnecessary furniture in some of the rooms and pictures weren't exactly like listing. The landscaping was overgrown and messy out front. There are lots of controls for the heating and air throughout the house, but they are very hard to use and no instructions posted. The hot tub was nice and enjoyed by our crew, but the cover lift...
United States
Paula L.
The price is AED 1,410
AED 3,587 total
includes taxes & fees
19 Jul - 20 Jul
7th Hole Chalet - Summer Getaway w Hot Tub, Sauna

Upscale and Family-Friendly in Wintergreen

Upscale and Family-Friendly in Wintergreen
Roseland
9.6 out of 10, Exceptional, (38 reviews)
"House was very clean and had all amenities needed for a great trip!"
United States
Hunter C.
The price is AED 2,865
AED 5,139 total
includes taxes & fees
31 Jul - 1 Aug
Upscale and Family-Friendly in Wintergreen

Mountain Retreat: Year-Round Getaway, Pup Friendly

Mountain Retreat: Year-Round Getaway, Pup Friendly
Laurel Ridge
The price is AED 1,219
AED 2,446 total
includes taxes & fees
13 Jul - 14 Jul
Mountain Retreat: Year-Round Getaway, Pup Friendly

Hot Tub | Fire Pit | River | State Park | King Bed

Hot Tub | Fire Pit | River | State Park | King Bed
Wingina
9.6 out of 10, Exceptional, (13 reviews)
"The house was cozy, comfortable and clean. It's secluded nature setting was a perfect getaway. The hot-tub was a great treat as much as the sound of the stream and view. "
United States
Melissa C.
The price is AED 540
AED 1,274 total
includes taxes & fees
20 Jul - 21 Jul
Hot Tub | Fire Pit | River | State Park | King Bed

Hot Tub | King Suites | Outdoor Fireplace & Lounge

Hot Tub | King Suites | Outdoor Fireplace & Lounge
Wingina
10.0 out of 10, Exceptional, (1 review)
"We were so happy with our experience here! We rented this house and another house with the same owners, less than 10 minutes away from each other (both in Wingina). The 2 houses were each about 1/2 hour away from the seminary in Dillwyn…great location. Thank you for sharing your beautiful houses with us!"
United States
Jeff B.
The price is AED 625
AED 1,347 total
includes taxes & fees
3 Aug - 4 Aug
Hot Tub | King Suites | Outdoor Fireplace & Lounge

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (36 reviews)
"This was a wonderful, private, modern place to stay! We were here for a visit to Pippin Hill and this was the perfect place!"
United States
Shiloh F.
The price is AED 657
AED 1,534 total
includes taxes & fees
14 Jul - 15 Jul
Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven

Hillside Haven
2.0 star property
Faber
The price is AED 657
AED 1,357 total
includes taxes & fees
14 Jul - 15 Jul
Hillside Haven

Rosé All Day: Wine Country Getaway! Walk to Dining

Rosé All Day: Wine Country Getaway! Walk to Dining
Crozet
9.8 out of 10, Exceptional, (28 reviews)
"It was an excellent place to stay while in Crozet. Roomy and nice house."
United States
Carolyn R.
The price is AED 475
AED 1,206 total
includes taxes & fees
6 Jul - 7 Jul
Rosé All Day: Wine Country Getaway! Walk to Dining
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

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