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Check prices for these dates

Compare 430 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, (297)
"Our girls getaway was perfect! The house was just as described and very clean!!! I’m a stickler for clean and every nook and cranny was spotless. There was only one tiny inconvenience with the hot hub not being filled quite enough and maybe not cleaned before we came because of a film on the surface. But the owner/host responded immediately. We had everything we needed to fix the issue. The house is in a perfect location and located on a cul de sac, so very private. Would highly recommend and we...
The price is SAR 671
SAR 1,567 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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 SAR 671
SAR 1,550 total
includes taxes & fees
24 Mar - 25 Mar
Hillside Haven: Modern Retreat, Mountain Views

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

10.0 out of 10, Exceptional, (132)
"My family and I stayed here for a long weekend to make the most of some local hikes, end of season snow on the slopes and quality time together. The property met all of our needs and wants when we were browsing for availabilities. We had a hiccup accessing the property during initial check in (key code) but the property owners were helpful and got us in quickly. Their responsiveness eased my concerns right from the start, should we have needed them for anything else during our stay.What stood...
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!

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

9.0 out of 10, Wonderful, (2)
"The property is about a 5-7 minute drive to the Wintergreen resort. It was an excellent choice for multiple families who have kids. The downstairs area is full of entertaining games such as foosball, basketball, and darts. It also includes arcade games and multiple TVs. This area kept all the kids entertained whenever the adults were upstairs. "
NEW! Sleeps 14: Game Room, Fire Pit, & Hot Tub

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 SAR 624
SAR 1,737 total
includes taxes & fees
25 Mar - 26 Mar
Spacious + Serene Mtn Top Escape, 4 En Suites

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

10.0 out of 10, Exceptional, (289)
"This annual family trip was even better than we imagined! We would return in a flash no matter the time of year. The house, resort, and surrounding areas have so much to offer and everyone in our family, of all ages, had a blast. The house was definitely bespoke, the kitchen well-supplied, and all rooms were beautiful and comfortable. Nephew and niece were especially impressed with the basement offerings. Winter Storm Kingston caused some emergency panic about accessibility and snow removal, but...
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

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!!!

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

10.0 out of 10, Exceptional, (197)
"This was a perfect place for our bestie gathering. The location is beautiful...secluded and lovely. The house was truly impeccable. We loved the space. It was so well appointed with the little things that you may need. Simply awesome! Thank you to these great hosts!thoughtfully!"
Come and enjoy a beautiful view and relaxing time at Windy Knoll....

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

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!

Stuart Cottage: Walk to downtown + Sleeps 8

2.0 star property
10.0 out of 10, Exceptional, (6)
"I originally booked Stuart Cottage as I was looking for a place in Staunton while I was dealing with a serious family emergency. I am so lucky to have found this place on VRBO. Check-in process was a breeze, the property was immaculately clean, fully equipped kitchen with everything one could want (although I didn't have the opportunity to use it much - other than the coffee maker), nice sized bedrooms and baths, great washer/dryer, and excellent location in walking distance to Downtown. ...
The price is SAR 649
SAR 1,668 total
includes taxes & fees
24 Mar - 25 Mar
Stuart Cottage: Walk to downtown + Sleeps 8

White Rock Cabin

10.0 out of 10, Exceptional, (202)
"Scott & Christie are excellent hosts. Everything was beyond expectations."
White Rock Cabin

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 SAR 1,497
SAR 3,369 total
includes taxes & fees
27 Mar - 28 Mar
Luxury Home w/Mountain Views, Hot Tub, EV Charger, Play Equipment

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!

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

9.4 out of 10, Exceptional, (85)
"Booked last minute and property met all our needs. Clean, well stocked and good overall condition. Great value! We walked to the slopes both days which was the main draw to this particular house. A bit of a hike but totally doable if you’re in good shape. Nice being so close to the market for convenient provisions. We’d certainly stay there again!"
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Cozy Country small two bedroom home.

9.6 out of 10, Exceptional, (14)
"Loved staying there. Clean and "
The price is SAR 506
SAR 935 total
includes taxes & fees
27 Mar - 28 Mar
Cozy Country small two bedroom home.

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

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

9.8 out of 10, Exceptional, (174)
"Nice property and views. "
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

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

10.0 out of 10, Exceptional, (311)
"Fully equipped condo"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen Condo -Steps to Ski and restaurants

10.0 out of 10, Exceptional, (15)
"Cozy and clean. Fire place was lovely. Would return again! Thank you!"
The price is SAR 356
SAR 885 total
includes taxes & fees
1 Apr - 2 Apr
Wintergreen Condo -Steps to Ski and restaurants

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

9.6 out of 10, Exceptional, (297)
"Our girls getaway was perfect! The house was just as described and very clean!!! I’m a stickler for clean and every nook and cranny was spotless. There was only one tiny inconvenience with the hot hub not being filled quite enough and maybe not cleaned before we came because of a film on the surface. But the owner/host responded immediately. We had everything we needed to fix the issue. The house is in a perfect location and located on a cul de sac, so very private. Would highly recommend and we...
The price is SAR 671
SAR 1,567 total
includes taxes & fees
13 Apr - 14 Apr
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
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.