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Compare 349 Vacation Homes in Wintergreen with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (295)
"Excellent"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

10.0 out of 10, Exceptional, (288)
"The house was the perfect layout! Everything you needed was provided! Will definitely stay again!"
Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (26)
"Imagine a house for 7 adult couples to relax, drink and be merry without feeling cramped. This house was absolutely astonishing. Each couple had a room with bathroom. The decor and upgrades, in every single room, offers inspiration and is 1,000% upscale.The great room view is breathtaking and the home is in close proximity to the slopes.This was my first time using VRBO and the owner was very responsive to all messages throughout the process. He has set the bar high.We will visit again!"
Insane Mountain Views - New Listing

Hillside Haven: Modern Retreat, Mountain Views

10.0 out of 10, Exceptional, (23)
"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 1,530 total
includes taxes & fees
17 Mar - 18 Mar
Hillside Haven: Modern Retreat, Mountain Views

Luxury Home w/Mountain Views, Hot Tub, EV Charger, Play Equipment

9.6 out of 10, Exceptional, (5)
"We stayed for two nights at this property - 6 adults, a 5 year old and an 18 mo old. We really enjoyed the stay. Beautiful house and property a close drive to many wineries and breweries. Crozet is about 15 minutes away if you need groceries, etc. The upstairs is fairly protected sound-wise from downstairs which was a nice touch if you have kids with you. One bedroom is downstairs and three are upstairs. My only minor quibbles were the lack of curtains in two bedrooms, and one of three cooking...
The price is AED 1,465
AED 3,298 total
includes taxes & fees
26 Mar - 27 Mar
Luxury Home w/Mountain Views, Hot Tub, EV Charger, Play Equipment

Restored Double Log Cabin on 400 Mountain Acres

10.0 out of 10, Exceptional, (228)
"Property was beautiful, the views amazing. Feel likt the host thought of everything a family would need. Definitely comfortable and cozy. Super beautiful too. Would recommend and stay again there!! Thank you !"
Restored Double Log Cabin on 400 Mountain Acres

Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

10.0 out of 10, Exceptional, (131)
"Excellent house close to the slopes"
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

Modern Luxury Mountain Home within Wintergreen Retreat Collection

9.8 out of 10, Exceptional, (46)
"Spacious home that worked well for our group of 15. Having a separate hangout area for the teenagers was a big bonus. Nice, flat parking with a short drive down to the slopes. Functional kitchen with plenty of plates and silverware for all the guests. Only wished for a few more hooks to hang up everyone’s ski gear."
Modern Luxury Mountain Home within Wintergreen Retreat Collection

Spacious + Serene Mtn Top Escape, 4 En Suites

10.0 out of 10, Exceptional, (34)
"Hosts were great getting everything set for a last minute trip before a big snow storm. Very clean property; looks exactly as described in photos. 2-3 min drive from the base of the mountain."
The price is AED 611
AED 1,692 total
includes taxes & fees
13 Mar - 14 Mar
Spacious + Serene Mtn Top Escape, 4 En Suites

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

9.8 out of 10, Exceptional, (20)
"The house was nice and perfect for our group of three families with small children. Ideally, there would have been some basics in the house like oil and coffee filters. The garbage situation is a bit tricky as you have to take stuff to the dump yourself. Not a huge deal as the dump is on the way to wintergreen. But the dump is closed on Monday, which can present a problem if your check out is on Monday."
Modern 4 bd Log Cabin in Afton on 151 Brew/Wine Trail/Hike/Ski

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

10.0 out of 10, Exceptional, (42)
"Everything was as advertised- family of 6 was well accommodated for a Thanksgiving weekend. Very cold windy and snowy outside but house was warm and comfortable. Very large kitchen was well suited for preparing Thanksgiving dinner. "
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!!!

Afton escape centrally located on the brew trail

10.0 out of 10, Exceptional, (19)
"We stayed here for our 21st anniversary and it couldn’t have been a better place. Thanks for your hospitality!"
Afton escape centrally located on the brew trail

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

9.6 out of 10, Exceptional, (24)
"Couldn’t have been more pleased with our stay! Property was as advertised and our host was very gracious."
The price is AED 477
AED 797 total
includes taxes & fees
13 Mar - 14 Mar
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Stuart Cottage: Walk to downtown + Sleeps 8

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a great time in Staunton visiting family and the home worked out great for our group. "
The price is AED 621
AED 1,600 total
includes taxes & fees
13 Mar - 14 Mar
Stuart Cottage: Walk to downtown + Sleeps 8

Book for Spring! Nelson 151, MTN views!

10.0 out of 10, Exceptional, (14)
"We had such a nice relaxing vacation. The views were beautiful. Great resource provided for local activities, trails, restaurants, etc."
Book for Spring! Nelson 151, MTN views!

4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

9.4 out of 10, Exceptional, (3)
"The property was well stocked and the location was excellent. There was plenty of firewood for the fireplace and the hot tub was perfect after a long day of skiing at the resort. "
4min to Ski! Mntn Views Hot Tub Fireplace 52" Roku

The newest and largest edition to the Wintergreen Retreat portfolio!

9.6 out of 10, Exceptional, (40)
"We had a lovely time in this lovely house. "
The newest and largest edition to the Wintergreen Retreat portfolio!

Cozy Country small two bedroom home.

9.6 out of 10, Exceptional, (14)
"Loved staying there. Clean and "
The price is AED 496
AED 899 total
includes taxes & fees
13 Mar - 14 Mar
Cozy Country small two bedroom home.

4 BR cabin mins to trails & breweries pets welcome

9.8 out of 10, Exceptional, (21)
"Excellent location, clean, comfortable, would stay again!"
The price is AED 903
AED 2,450 total
includes taxes & fees
13 Mar - 14 Mar
4 BR cabin mins to trails & breweries pets welcome

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

9.8 out of 10, Exceptional, (173)
"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "
Fantastic Mountain & Valley Views! Top of the Mountain & Close to the 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.

9.6 out of 10, Exceptional, (295)
"Excellent"
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Wintergreen Condo -Steps to Ski and restaurants

10.0 out of 10, Exceptional, (12)
"Short walk"
The price is AED 349
AED 874 total
includes taxes & fees
13 Mar - 14 Mar
Wintergreen Condo -Steps to Ski and restaurants

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

10.0 out of 10, Exceptional, (310)
"I’ve stayed here a few times now with various members of my family and all of us love this place! The accommodations are great, the place is well stocked with careful attention to detail, and we always look forward to returning. Thanks again for a 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.