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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 437 Vacation Homes in Wintergreen with updated reviews, rates, and availability.

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Exterior

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10.0 out of 10, Exceptional, (240)
"Great hosts and were very friendly"
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
Property grounds

Bud's Place, Southern Charm in the Shenandoah Valley of Virginia

10.0 out of 10, Exceptional, (27)
"This house was so cute and the property/atmosphere was perfect. We all loved it the children could run around with the dogs and the house was super cozy. Will definitely be staying here again when we are in the area "
Bud's Place, Southern Charm in the Shenandoah Valley of Virginia
The Landmark: Luxury In Downtown Staunton
Fridge, microwave, oven, dishwasher

The Landmark: Luxury In Downtown Staunton

10.0 out of 10, Exceptional, (17)
"Great to be able to get landmark and hunker down together for extended family and pets"
The Landmark: Luxury In Downtown Staunton
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Terrace/patio

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (302)
"Fun, fun times in a short stay. Location was perfect ! "
The price is AED 657
AED 1,539 total
includes taxes & fees
27 May - 28 May
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
Property grounds

NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

9.8 out of 10, Exceptional, (6)
"Great house, awesome game room!"
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
Exterior

NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️

10.0 out of 10, Exceptional, (23)
"Wonderful place to stay for a family reunion-kids loved the pool and frisbee golf. The owners even had pool toys for the kids to use! "
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
Cozy Country small two bedroom home.
Smart TV, DVD player

Cozy Country small two bedroom home.

9.6 out of 10, Exceptional, (14)
"Loved staying there. Clean and "
The price is AED 496
AED 891 total
includes taxes & fees
18 May - 19 May
Cozy Country small two bedroom home.
Insane Mountain Views - New Listing
Smart TV, fireplace, DVD player, books

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (28)
"If you’re traveling with a large group or multiple families- this is the property for you.There’s too many things to comment on with this beautiful home. The views- breathtaking. The rooms private, luxurious l, and accommodating and the location was very convenient "
Insane Mountain Views - New Listing
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Outdoor spa tub

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

10.0 out of 10, Exceptional, (42)
"Check-in process was a breeze, communication with the hosts was super easy and consistent. Place was very clean and exactly as appears in the pictures. My group had an amazing time and loved the location of this property. Would 110% stay here again!"
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!
Afton Farmhouse - Mountain Views off Route 151
Smart TV, books

Afton Farmhouse - Mountain Views off Route 151

9.8 out of 10, Exceptional, (19)
"The house was really cozy with lots of space inside and outside to enjoy. We enjoyed playing games, sitting by the fire inside and outside, and visiting the local wineries and breweries. Ashley was an excellent host and quick to respond with any questions. "
The price is AED 652
AED 1,718 total
includes taxes & fees
20 May - 21 May
Afton Farmhouse - Mountain Views off Route 151
Hillside Haven: Modern Retreat, Mountain Views
Outdoor dining

Hillside Haven: Modern Retreat, Mountain Views

10.0 out of 10, Exceptional, (24)
"The place was exactly as advertised. We had a great experience. Host was super responsive, would absolutely stay there again. "
The price is AED 657
AED 1,501 total
includes taxes & fees
11 May - 12 May
Hillside Haven: Modern Retreat, Mountain Views
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
Exterior

Come and enjoy a beautiful view and relaxing time at Windy Knoll....

10.0 out of 10, Exceptional, (200)
"Everything with this house exceeded expectations!! Super clean and plenty of space with beautiful views. "
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
Book for Spring! Nelson 151, MTN views!
Fridge, microwave, oven, stovetop

Book for Spring! Nelson 151, MTN views!

10.0 out of 10, Exceptional, (15)
"Great stay. I only wish the 2 days of rain had been snow!"
Book for Spring! Nelson 151, MTN views!
Cozy Craftsman: Newly Renovated/Downtown Staunton
Exterior

Cozy Craftsman: Newly Renovated/Downtown Staunton

9.8 out of 10, Exceptional, (20)
"Great place to book if visiting family in the area. Clean, centrally located and has everything you need inside. "
Cozy Craftsman: Newly Renovated/Downtown Staunton
The Firefly Springhouse
Exterior

The Firefly Springhouse

10.0 out of 10, Exceptional, (25)
"The cottage was cute and the host was very friendly and helpful. The perfect place to stay for a couple nights."
The price is AED 338
AED 458 total
includes taxes & fees
11 May - 12 May
The Firefly Springhouse
Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski
Interior

Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski

10.0 out of 10, Exceptional, (21)
"Spent Christmas here with grown children. Excellent location close to hiking trails, vineyards and craft breweries. Very well maintained property - cozy, comfortable and peaceful."
Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
Terrace/patio

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

10.0 out of 10, Exceptional, (16)
"Amazing! I could spend hours at examining the decorations that each seem to have a story of their own. No detail overlooked! Felt like a step into the past ☺️"
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!
White Rock Cabin
Property grounds

White Rock Cabin

10.0 out of 10, Exceptional, (207)
"Above and beyond on everything highly recommend staying here"
White Rock Cabin
View With a Room │ Mountain Home in Wine Country
Property grounds

View With a Room │ Mountain Home in Wine Country

10.0 out of 10, Exceptional, (7)
"This house was so lovely, and so well stocked! The owners thought of everything you could possibly want. Very pleased! "
View With a Room │ Mountain Home in Wine Country
Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.

10.0 out of 10, Exceptional, (3)
"We had a group of nine wonderful ladies get together. Accommodations were perfect. We had plenty of space to enjoy ourselves. We talked, laughed and even crafted. Could not ask for better property host! Highly recommend!!!"
Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.
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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Other property types in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Terrace/patio

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

9.6 out of 10, Exceptional, (302)
"Fun, fun times in a short stay. Location was perfect ! "
The price is AED 657
AED 1,539 total
includes taxes & fees
27 May - 28 May
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

10.0 out of 10, Exceptional, (235)
"Absolutely loved my second stay at the gorgeous property! The sunrise and sunset views can’t be beat. "
Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (313)
"Heather’s place was cozy, well-stocked with every detail considered. Heather was communicative and helpful. Great stay."
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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.