Kid-friendly holiday rentals in Wintergreen Resort

We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!

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!

very nice house in an amazing place. We were with friends for a wkd and it was the perfect aera. I recommend this house. Clear communication with Deborah.

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!

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

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.

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.

We loved Saltbox! Kristy was a great and very responsive host. We enjoyed the layout and cleanliness of the house, as well as it’s closeness to Wintergreen. We would definitely stay here again.

Great cozy spot in Lovingston! Ed was a wonderful host, very responsive and helpful. Despite all the rain we were able to have a lovely weekend getaway. Wineries and restaurant options close by.

Desire and Scottys place was even cuter than the pictures. it had everything we needed and things we didn't realize that made our stay a home away from home. It was a peaceful place to relax in after a day of hiking and wineries in the area. It was also nice to be able to walk to dinner and explore town. Will definitely come back when we are in the area again.

This place was awesome! Clean and quiet with some amazing views. There’s an abundance of wild life so be mindful when driving. The host is amazing. There’s hot chocolate and a beautiful fire place. Blankets if you choose to sit on the balcony with some hot chocolate and enjoy the view. Many food choices to choose from that aren’t too far. Would definitely stay here again and recommend you do too.

The stay at Laurie’s was great and she was super helpful dealing with our admittedly messy scheduling. The location is great by the wharf and while there is some noise due to the age of the building we were not bothered at all and slept great, we would definitely stay here again!

A home away from home. Susan has thought of the little things one needs when traveling. Her place is extremely clean, lovely space, and the perfect walk from everything Staunton has to offer. It's our 4th or 5th time staying with her- enough said.

Fun weekend trip! I was in Staunton for a show at the American Shakespeare Center and stayed an extra day to explore the area. It just happened to be opening weekend for the farmer's market as well as the start of the outdoor shopping/dining season on Beverley Street. Martha's place is the perfect central location for exploring this very walkable town - I enjoyed seeing the Woodrow Wilson Museum (and garden in the back with lots of spring flowers blooming), Mary Baldwin campus, Trinity Church, etc. Martha's apartment is so comfy and clean, and has all the amenities. The bed is amazingly comfortable, the kitchen is well equipped, and the living room couch/tv setup is nice for relaxing with a show or movie in the evening. There are so many little touches throughout the apartment that let you know that Martha has thought of everything to make her guests feel at home. I can't say enough about this charming place and wonderful host!

Jamie's space is super clean and comfortable. It was obvious that the hosts devoted much care and attention to their guests’ needs. The photos are accurate, with the apartment being even more lovely in person. Easy walk to downtown and many Staunton attractions. We parked in the gravel lot behind the house since it was mostly empty. The driveway is narrow with a steep-ish decent into the lot. (It’s Staunton - the whole town is hilly.) But, for those who don’t want to do that, there were spots on the street. Would stay here again.

Great host very accommodating and responsive , great location close to everything you’d want to do in the surrounding areas, very scenic and peaceful and the Airbnb itself was clean, quiet, and very fairly priced. Perfect quick trip to the mountains. Thanks again!

Had a great stay for a few nights in this condo. Comfortable and clean as a lovely escape while we enjoyed local hikes and breweries. Convenient to the wintergreen market which was helpful for what we may have forgotten or for anything else we wanted. Looooved having the wood burning fireplace too! We’d love to come back.

We had a wonderful stay at this Wintergreen condo. Location was great and we loved we could bring our dog. The place was very clean and had all necessities we needed. It was very cozy and we felt right at home. Kim was very responsive and friendly to deal with. All the instructions were clear and easy. We would definitely recommend and would come back!

Beautiful location with the daily sunrise over the blue ridge mountains is captivating. Kimberly who manages the property is the provides the best customer service I've ever had at Air B&B . (Got well over 100 nights in withAirB&B)

Lisa's condo was fabulous! It was decorated beautifully and in a very peaceful location. It was great not having to walk up and down multiple flights of stairs. If you need anything, she is quick to answer. It was the cleanest dog friendly Airbnb that we have ever stayed in!! We have a hypoallergenic dog so I appreciated not being covered in dog hair. We will definitely be staying again in the future! Thank you, Lisa!

Great place. Beautiful view. Everything you’d need.

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.

Mary’s place was exactly what we needed for our family with small children. The kids loved eating on the deck and being able to sleep in the same room but in their own bed. They had games available and everything was nice and clean. Mary was also quick to respond with any questions we had. We would definitely stay here again!