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

Hillside Haven: Modern Retreat, Mountain Views
10.0 out of 10, Exceptional, 15 reviews
"Very nice place to stay and located within 30 minutes of Monticello and winery’s! Very quite area and fully stocked kitchen!!"
The price is $194
$427 total
includes taxes & fees
Jun 12 - Jun 13
Hillside Haven: Modern Retreat, Mountain Views
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, 220 reviews
"Bill and Cynthia are such amazing hosts and the property inside and out exemplifies it. What a great place to stay for some serious rural R&R! The property was very clean. They have thought of everything one would need for a delightful get away. If you forgot anything, just ask and they are sure to help one way or another. The Fresh eggs, courtesy of their chickens, were a treat and the farm animals are such fun…esp Posy, Zoey and Hemingway. We hope to return soon for a longer retreat! Thank you...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
9.8 out of 10, Exceptional, 55 reviews
"We had a lovely stay. The area was gorgeous and the house was comfortable and perfect for our family of 5."
Mountain Chalet – Panoramic Views of Blue Ridge Mountains!
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For long family stays, girls wine weekends. Heated pool, hot tub, game room. Walk to brewery.
10.0 out of 10, Exceptional, 19 reviews
"My family and I had a great time at this property with the air hockey, dart board, firepit, & hot tub. The kitchen was well-stocked with non-stick cookware, having everything one might need to cook. We cooked many of our meals, so this was appreciated (there's a limited number of restaurants in the area, but we like to cook). Communication with the owner was very easy and good."
The price is $379
$469 total
includes taxes & fees
Jun 3 - Jun 4
For long family stays, girls wine weekends. Heated pool, hot tub, game room. Walk to brewery.
Upscale and Family-Friendly in Wintergreen
10.0 out of 10, Exceptional, 9 reviews
"This year’s gathering of our ever growing tribe of children, grands and canine landed us as close to the Heavens as possible. This property was perfectly set up for sleeping arrangements, meal sharing, dog convenience and activities for all ages… the climbing wall was especially popular with our young gymnast and the free-standing video arcade was nostalgically fun for all ages. Of course, being March, the hot tub and sauna got used quite a bit too. The ultimate lure of this property...
Upscale and Family-Friendly in Wintergreen
The newest and largest edition to the Wintergreen Retreat portfolio!
9.8 out of 10, Exceptional, 29 reviews
"Great fit for our larger multi family group. Short drive to the skier drop off/ pick up and great accommodations in the house. We’ve stayed multiple years and I suspect we will stay multiple more!"
The newest and largest edition to the Wintergreen Retreat portfolio!
Big Bronze house Waynesboro
10.0 out of 10, Exceptional, 6 reviews
"Needed a place for family to gather for UVA graduation weekend. The house was a 30 minute easy drive to campus grounds. Also very short drive to Staunton restaurants and great proximity to Afton mountain vineyards. Easy check in, WiFi, ample parking (grass). Enjoyed our stay."
The price is $189
$430 total
includes taxes & fees
Jun 2 - Jun 3
Big Bronze house Waynesboro
Oak Tree Cottage: Beautiful farm with mountain views.
10.0 out of 10, Exceptional, 43 reviews
"We traveled here with 6 adults and 3 children and had a wonderful time! The cottage is in a beautiful location and close enough to get to stores and restaurants. It’s incredibly clean, well-appointed and perfect for big groups. The owners are very friendly. We enjoyed exploring outside and playing games with the kids. There are also lots of hiking options nearby. We were there for a wedding but we would definitely come back!"
Oak Tree Cottage: Beautiful farm with mountain views.
Mtn Home w/ Nature Preserve Views By Hiking Trails
9.0 out of 10, Wonderful, 43 reviews
"Beautiful property, kind host. Exactly what we'd hoped for!"
Mtn Home w/ Nature Preserve Views By Hiking Trails
Cooler in the mountains, with hot tub.
9.8 out of 10, Exceptional, 61 reviews
"My husband and I were looking for a place to disconnect and get back to us. This was the perfect place. It was very quiet and relaxing. We plan on hoing back again in a month or so. We were also able to meet up with a local that helped taxi us to Bold Rock."
Cooler in the mountains, with hot tub.
Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting
10.0 out of 10, Exceptional, 119 reviews
"We loved Afton Station Cottage! We were looking for a nice place to stay for our trip to the Blue Ridge for hiking and sightseeing, and located in the Charlottesville-Shenandoah Valley wine country. We couldn’t have found a more homey and comfortable place. Communication with our hosts easy and convenient throughout our stay. Pre-check in information was perfect. Our hosts also gave us some great information about the area, including suggestions for places to see and visit. We enjoyed one of...
Afton Station Cottage -Beautifully Renovated Blue Ridge Scenic Historic Setting
Sweet Darling House: Enchanting historic home; walkable to downtown
10.0 out of 10, Exceptional, 2 reviews
"This little housse is like a very good cabin. 2 private bedrooms with one shared bath. Very tastefully decorated. It had everything we needed for a good stay. New appliances and heating system, back deck has wonderful private view of the woods. Very quiet and restful, yet right in the middle of Staunton. All amenities were minutes from the house. Very clean and had a very interesting history to the house. Yet great modern renovation. Would definitely visit again. The host even left wine for us...
The price is $166
$269 total
includes taxes & fees
Jun 11 - Jun 12
Sweet Darling House: Enchanting historic home; walkable to downtown
Hot tub+Game Room+Fire Pit+Views+King beds in spacious family-friendly house
10.0 out of 10, Exceptional, 6 reviews
"Perfect as described for families with children - game room was a huge hit. The entire house was clean and provided everything that we needed for a multi-day adventure. Host was excellent."
Hot tub+Game Room+Fire Pit+Views+King beds in spacious family-friendly house
Rustic Getaway with Fireplace - Walk to Slopes!
9.0 out of 10, Wonderful, 8 reviews
"We loved this unique property! The circular fire place was a big hit, and there was plenty of space for both our families with teens to hang out. The downstairs set up was a little different as you had to go through the second master to get to the game room, 2nd bathroom and laundry. Great hot tub and really nice coffee bar/bar bar. My only critique is that the kitchen ware selection was limited (the listing does say basic). There wern’t really pans big enough to cook meals for 7 people so we...
Rustic Getaway with Fireplace - Walk to Slopes!
Luxury Home w/Mountain Views, Hot Tub, EV Charger
9.0 out of 10, Wonderful, 2 reviews
"Nice and peaceful place with mountain view"
Luxury Home w/Mountain Views, Hot Tub, EV Charger
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
The price is $500
$1,008 total
includes taxes & fees
Jun 2 - Jun 3
Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, 218 reviews
"Susan's place was a perfect place for me to gather with my children, their significant others, and grandchildren. The house was as advertised! it was secluded and quiet and the kitchen came fully appointed with pots, pans, utensils, plates, silverware, you name it. We cooked all our meals at the house and had everything we needed. Thank you Susan for letting us stay in your peaceful, mountain cabin."
Restored Double Log Cabin on 400 Mountain Acres
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
10.0 out of 10, Exceptional, 187 reviews
"Home was very clean and well stocked. Front porch had amazing view and wildlife was abound. We were extremely pleased with our stay and will definitely be returning."
Come and enjoy a beautiful view and relaxing time at Windy Knoll....
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
10.0 out of 10, Exceptional, 19 reviews
"We had an amazing stay while in the area to attend our granddaughter's wedding. It was a perfect place for our family to spend time together. The younger grandchildren had plenty of space to play together. It was a great experience and throughout the process the host was very quick to respond to any questions. Thank you for helping our family make some amazing memories."
NEW! Secluded Farmhouse Winery, Hike, Lg Group❤️
Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!
9.2 out of 10, Wonderful, 109 reviews
"Great location, amenities, spacious, responsive and helpful host. Highly recommend this house to large groups or families visiting Wintergreen."
Private creek, 5 minutes to slopes, under new management, pet friendly, hot tub!
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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.

Other property types in Wintergreen

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
9.6 out of 10, Exceptional, 264 reviews
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot tub was wonderful, the wifi works great (we had one doing online school and one work), and all was just as the listing described. It was a great place to stay for a Liberty University graduation. If...
The price is $179
$414 total
includes taxes & fees
Jun 2 - Jun 3
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, 272 reviews
"We thoroughly enjoyed our stay at this condo. Quiet neighborhood and very comfortable. Appreciated all the basics offered that other rentals do not such as soap, garbage bags, toilet paper. But the owners went above that and had lotions, specialty soaps, cleaning supplies etc. Well stocked kitchen for cooking. While it was just the two of us we liked that there were games available for families and there was a nook upstairs for kids to get away. Highly recommend and would definitely come visit...
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, 209 reviews
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
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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