Pet-friendly vacation rentals in Wintergreen Resort

A Perfect Stay – Comfortable, Charming, and Convenient! We had a wonderful stay at Bevin’s Airbnb! From the moment we arrived, we felt right at home thanks to Bevin's warm hospitality and thoughtful touches throughout the space. The beds were incredibly comfortable, making it easy to relax and get a great night's sleep after a day of exploring. One highlight was definitely the hot tub—such a perfect way to unwind! The decor is vibrant, colorful, and so tasteful. The whole place felt cozy and inviting, yet stylish. It truly enhanced the overall experience and made the space feel like a home away from home. Bevin is an exceptional host. She was incredibly responsive, always checking in to make sure we had everything we needed; her kindness made the experience even more special. The location is perfect— close to downtown Charlottesville and the nearby wineries! making it an ideal base for anyone looking to enjoy both the local culture and the beautiful countryside. HIGHLY RECOMMEND!

My family had a wonderful time staying at this beautiful house. It was a perfect fit for us. There was plenty of room for everyone and we had a great time playing cards in the evening and watching movies. My 4 and 2 year old grandsons looked forward to going to bed at night so they could take a bath in the jacuzzi tub. The house had everything you could possibly want. The hot tub was a hit with my grown children. We look forward to returning in the future.

Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!

We had a wonderful time at the cottage. Elise and Preston were incredibly hosts, and the cottage was full of thoughtful amenities and is beautifully designed. The area is gorgeous with plenty to do while still being in the peace and quiet. Our daughter had a blast with the farm animals, running around the large oak tree and playing in the loft. It was perfect for our little family - we'll definitely be back!

Great place in Wintergreen! We stayed in Spring and everything was quiet and the foliage was vibrant. Our family went hiking and exploring everyday, and enjoyed the food and drink down in the valley. There is a nice trail in Wintergreen if you can find the overlook off Old Appalachian trail. Hot tub was a plus for sure! Enjoyed the trails in the neighborhood and watching the golfers. All the amenities you could ask for and a clean tidy home!

My children and I had such a wonderful time at the lodge. The view is priceless. We enjoyed each and every day and hated to leave. The beautiful outdoor deck with amazing views, the hot tub, the wall of windows with the very best Mountain View and the game area downstairs were all highlights for us. We appreciated and took advantage of the local recommendations and can’t wait to return. Lauren was a wonderful host and answered all of our questions immediately throughout the stay. We hope to be back!

My man and I had a wonderful time having a quiet and private weekend getaway. The place is so cozy and the hosts are so welcoming. It’s a beautiful view off the back porch. One of the highlights of my weekend was getting to spend time with Bilbo the cat. He was so snuggly and gave us a warm welcome as soon as we arrived! Would love to come back here again!

Beautiful space to spend a weekend with friends. Lovely views from each room and the deck. Walkable hiking trails with waterfalls. Would stay here again.

We had such a lovely time at the ‘small house’! Jennifer was quick to respond with any questions we had (about the property and the town)! We loved playing yard games and hanging out by the water. The kitchen was stocked with spices and all the things we needed to spend time together cooking. We plan to visit again in the Winter!

Susan’s farm house was perfect for enjoying a relaxing getaway with plenty of space for multiple families and kids. All of the spices are very large and honestly it’s better in person than in the pictures. We would recommend it to anyone and return again! The kitchen was nicely stocked with everything you could need. And it was great being right on the winery.

I absolutely loved my stay here in Staunton! The property was beautiful and exactly as pictured. It’s a 10 minute walk to town, which made it the perfect location. I will definitely stay here again when I return to Staunton.

Great farm house and wonderful experience. Was so nice to be able ti being the dogs. They loved the field.

We had a great stay at the Critzer House. It was just as described and perfect for our two families of four. Plenty of room for all of us to hang out together or retreat to separate spaces for some quiet time. The sunroom was great for starting the day with coffee and finishing with adult beverages. The location was ideal...30 minutes or less to incredible hikes, breweries, wineries, and distilleries. Easy walk to Blue Mountain Brewery for dinner after a long day exploring the beautiful surrounding area.

Lovely spot in the mountains! Perfect if you're planning to hike! The space was cozy and clean; we brought our two dogs and had fun all sitting by the fire inside! It was thoughtful of her to have laundry detergent pods for us to use. The master bed was comfortable, which I don't find myself saying too often in Airbnbs! Overall, it was peaceful and quiet - a great getaway from the city.

Simply put, this could not have been a better stay. This place had everything we needed and was a short and super easy trip to the slope. The golf course being closed also made it easy for us to get our pups energy out. I highly recommend this spot to anyone coming to stay at the resort. Carol did amazing job communicating and even was willing to work with us on check out time so we could hit the slopes on chekout day. Will definitely be renting again next season if available.

This house was amazing to stay at! The plan was just to find an Airbnb to stay at while we skied at wintergreen, but we ended up getting rained out and spent almost the whole time in the house. I was so fun the house is full of surprises and fun board games we weren't board for a minute! The beds were super comfortable, and the kitchen has everything you need to cook!

My fiance, our dog, and I had a wonderful stay at Susie's! The condo was well stocked with anything you may need during your stay. The dog bowls and towels were a thoughtful addition right as you walked in. The bed was comfortable and we loved having the TV up there to unwind after a day of hiking around nearby trails. We ended up having to reschedule the days that we were coming, and Susie made that process very easy. We will definitely be staying here again next time we come to the area!

This was the best airbnb for kids we have ever stayed at! The lay out was absolutely perfect for 3 families and 11 kids! Will definitely be back. The owners thought of everything and the cots in the closet came in very handy. 10/10

I’d argue that this is one of the best places to stay in Wintergreen. The cabin itself is perfect. We are a young family and it was comfortable, clean, and had everything we needed. The location is also perfect. It is very close to all the attractions on the resort. Clay was a great host as well. The perfect amount of communication; engaged without being intrusive. I would recommend this place to anyone who wants to be sure their trip is easy and successful!

Pip's place is close enough to all the features that Wintergreen Resort offers to make them easily accessible, but far enough away to give you space and quiet. It backs up to the golf course so the back has a lovely setting. We were especially grateful that the place is dog friendly. We would totally recommend this spot and would stay again in the future.

We had a great stay; the house looked exactly like on the photos, and was properly cleaned before we arrived. Charlotte was very responsive, gave us great recommendations for local kid-friendly hikes and helped quickly resolve any issues that came up during our stay.

The view is stunning!! Nothing beats waking up on top of a mountain! Mary Beth and Gregg have very helpful instructions to find their home. The house was clean, comfortable, cozy, and well stocked! They had great recommendations for restaurants and shopping in the area. They were very communicative and responded quickly with any questions we had. We really enjoyed our stay and what Wintergreen had to offer! Wintergreen is a very beautiful place!

Lindsay’s place was perfect for our family’s ski weekend. The condo was spacious and had everything we needed. The views were amazing! Lindsay was a great communicator and very responsive host. Highly recommend!

Ritta's condo is clean, spacious and comfortable, situated in a woodland sanctuary of peace and quiet. Loved each morning and evening of spacious solitude.