House holiday rentals in Wintergreen

We spent a great week at Susan’s place. The location and views were terrific. The house was extremely well stocked and the host was super responsive. Would highly recommend.

Camille's place at Wintergreen was perfectly situated for our weekend at Devil's Backbone. The house was clean and tidy, it was easy to find, and her directions and instructions for getting there and getting in the house were spot on. it's an adorable little place and has plenty of room with the three bedrooms. We would love to come back and rent again. Our dog loved it too!!

We had family from 3 different states meet. Check-in was easy and Shilpa accommodated the group of us for an early check in. We had a slight issue with the AC and the host had someone there within 30 minutes to assist. Enjoyed a nice relaxing week.

We stayed here for a bachelorette weekend and had a great time. The house was even bigger and cozier than I anticipated and the views were gorgeous. We loved being on the same property as Cardinal Point Winery and walked down to do a tasting/enjoy some bottles. The kitchen was stocked with all the tools we could have needed and the pool area was great!

We had an amazing stay at this beautiful condo in the mountains! The location is perfect for anyone looking to hit the slopes or tour the grounds – making it great destination year round. The condo itself is cozy, clean, and has everything you need for a comfortable stay. The kitchen was well-equipped, which made it easy to cook meals before heading out for the day. The beds were super comfortable, and we slept like babies every night! The host was incredibly helpful, providing us with all the information we needed for the resort, and even sent us local recommendations for dining and things to do in the area. Check-in and check-out were a breeze. Would definitely recommend this place to anyone looking for a relaxing, convenient, and picturesque retreat. We’ll be back next year for sure!

I was looking for a quiet place in the middle of the nature for our 10 years of marriage anniversary and I think we found the best one. Charlotte was so kind and helpful, she helped me surprised my wife with such a beautiful decoration. We were so impressed. My kids were so happy 😊😊 to see something different. If you’re looking for something really peaceful, nice, looking at the beautiful nature in the mountains, you are definitely at the right place. Thank you Charlotte for making our stay so special.😊😊😊😊 It was a really good experience and we definitely have to go back….

The cabin was great to stay at and had some pretty awesome views! Highly recommend the hiking trails. Overall, a really great place.

A wonderful property nestled in the Wintergreen Resort. While not part of the resort, the amenities and surrounding Breweries offered plenty to do while not relaxing in the hot tub or on the private deck. Beds were comfortable, and there was plenty of space for our family to spread out. Access to WiFi and movie channels were convenient and supplemented the secluded feel for a well balanced vacation. Highly recommend this rental for families and groups looking to get away for a relaxing and enjoyable time in the mountains. Bring your cameras and charge your phones to take pictures of the breathtaking views at and around the house!

It was a beautiful place that felt like home. The owners were amazing and responded very quickly. We will definitely come back!

Hone was truly beautiful! Recently renovated in a great mid century model. We had a group of 11 and we were all at home instantly! Will definitely stay there again!!

this private condo at wintergreen was perfect for my family and I, with a 15 month old it was very baby friendly and the view took our breath away. the host was very responsive and checked in before during and after the stay to make sure we had everything we r needed. I would 100% recommend this for your next getaway.

I enjoyed the stay and Beth was a great host! Everything was as described and she was extremely detailed in instructions to make the stay as easy as possible. I would recommend the stay for anyone wanting a mountain getaway or explore the Wintergreen area!

We choose this home for our 2025 family get together, we were 8 adults, 7 kids and a dog and we were more than comfortable! The house is beautiful! very spacious and very well organized and equipped with everything we needed! Something that stood out to me, comparing this stay with previous ones, there were large size shampoo, body wash and conditioner in every bathroom, as well as large hand soap and refills in every sink and plenty of dishwasher, laundry detergent, TP and paper towel!! That was very very appreciated! The outdoor deck area was just amazing! We created beautiful memories making s’mores and enjoying the hot tab! The kids loved the slide and play area! We truly loved our stay! The only thing that was not to our liking was the pool rules of 6 guests at the time, because we had to split up the family when this vacation was about spending time together, as we all live apart from each other, but this has nothing to do with the rental 🤷🏼‍♀️ We will comeback! 🧡

Chris and his manager runs an excellent property. The property provides many thoughtful items to make your stay comfortable, enjoyable and homey. Only negative is HOAs rule that limits renters access to resort amenities.

The house was awesome! Clean, comfortable, parking, beautifully decorated. Bed rooms, kitchen and bathrooms were amazing and stocked well. The views were amazing! Loved the covered seating area outside. Beautiful. Highly recommend the house!

Dru, from moment one was responsive and answered all my questions with joy. This house is truly just lovely and even bigger and more open concept than i thought it was going to be based on the photos. The master bedroom with a king size bed on the main floor was my favorite space (my room) i did not want to leave that shower and jacuzzi tub! It was truly enough space for all who came with me. I was their for my 30th birthday and we played 4 days of golf at Devils Knob and Stoney creek, and everyone had more than enough room there was 7 of us. The kitchen was also well stocked and appliances were easy to use. I loved the gas grill we had a day or 2 of hamburgers and hotdogs. Also, it is of course its close to devils backbone and some of the other breweries off of route 151, I've marked this house as a favorite of mine and will always look for availability here first :) thank you Dru for letting my ring in my 30's in your beautiful home!

Incredible Airbnb across the board! Truly 5 stars! Hope to be back!

A great get away with a beautiful view so close to so many wineries and breweries!

This was an ideal home for our family. Wake up and make a great breakfast in the stocked kitchen. Head out for a morning hike on one of the many great trails right around the corner. Then off for a day trip to Monticello or Staunton, and finish up in the hot tub. What's not to like!? Chris was very responsive to all our needs and put together a great welcome package to introduce us to the area. Hope to stay again!

We could not have asked for a better stay at the Vū. The home was as beautiful as the photos and the scenic background made it hard to leave. The house is near several vineyards and popular local spots but is set back from the road and neighbors, so felt very private. It’s clear that Emily put careful thought into every detail of the space, from the furniture to the amenities and fully-stocked kitchen. The screened porch was an exceptional feature. I stayed with my family and the space was more than enough to accommodate all of us. I absolutely recommend the Vū for your next mountain getaway!

Away from it ALL was just what we were looking for! Our family of 5, plus grandparents had plenty of space to relax. All of the amenities were as listed and very generous. The home is nestled in the woods and we spotted deer each evening. The kitchen supplies were so helpful. The home is about a 5 minute drive from Wintergreen resort. We would definitely stay here again!

The photos don’t do it justice - the views were immaculate, the location was excellent, and the home was a piece of serenity in Afton. Wendy was a wonderful host, very responsive, and kind. Would rent this again in a heartbeat.

Spent a long weekend at Tupelo, we had outdoor plans every day and we're able to come and go with ease. The amenities were great and the house was cozy. The night life near by was fun but, we had just as much fun cooking in and sitting by the fire too. It is certainly a home away from home.

Great house! We really enjoyed our stay for a weekend golf trip! Dinner at The Edge was close by and tasty, and the house was exactly as described!