Condo holiday rentals in Charlottesville

We really enjoyed it! Walking distance to all of downtown, the train was a little loud but not too bad!

Loved this place! Easy to find (saying a lot for Wintergreen...not always so easy!) with beautiful peaceful surroundings, and lovely amenities in a comfortable, clean & quiet place. Mary was super responsive to our questions. We recommend it!

We spent the weekend here to go snowboarding. It was very walkable to drop in at highlands or wait for the shuttle. Check in was easy and the kitchen was amazing. The view was incredible.

Amanda's condo was clean and cozy. There are many nice upgrades in the space, including an updated kitchen, master bath, and modern furniture. We could easily find what we needed. We felt right at home and would love to stay here again!

We had a fantastic weekend at Kim’s place. It was the perfect size for me, my husband, our daughter, and small dog. We enjoyed the balcony and the fireplace. Kim was super responsive and suggested local attractions. It was wonderful to unplug and be in the woods for a few days. Highly recommend!!

We loved our stay. It was exactly what we were looking for. The house is wonderful and very comfortable. Our kids loved the house, the area around it, and the hiking.

We absolutely loved our stay at the wintergreen resort. Jeff was an amazing host from start ro finsh. Highly recommend staying at the Wineglow. We look forward to staying there again.

I stayed a month at Carlos’s beautiful condo. It felt like the woods and golf course were within arm’s length due to the large windows along two walls. I could tell that a lot of planning went into equipping the kitchen. In addition to the coffee makers and toaster, two of my favorite items were available. A blender and a very fast water heater for a quick cup of cocoa. Everything was spotless with plenty of towels and linens. I was very comfortable and the neighbors were very friendly. I only had one incident of getting locked out due to a maintenance crew error. I was shocked at how fast Carlos responded to my message and within 10 min. I was back in the condo. Amazing communication! I would not hesitate to stay there again. It would be stunning in the winter too with the cozy fireplace. Carlos is the perfect host.

Perfect cozy getaway with beautiful views. Great location within walking distance to golfing, Nature Center, pool, spa & food.

This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!

Susie’s place was PERFECT for my weekend of solitude and peace. I was able to relax and just take it easy in a comfortable home with a beautiful view. The home was clean and felt so comfortable. There were lots of personal touches that really show Susie put a lot of thought into the space. For example, the motion sensor nightlights in the bathrooms. And the dimmable lights in the bedroom. Check in and check out instructions were very clear and easy to follow, she even included a map of where to park! I can’t say enough great things about this experience.

Very clean. Recently updated in very nice condition. Everything worked well. Great value!

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)

My wife and I really enjoyed a weekend getaway at Mikki’s place. The condo has a great location with beautiful views and access to nearby Wintergreen amenities, and we took advantage of the less than 20 minute drive to multiple of the Nelson 151 breweries. Mikki is very responsive and we appreciated her recommendations and help in getting us get access to a nearby pool. Would stay again!

Super clean condo with everything we needed. Perfect for a stay in Wintergreen!

You don’t need many word for this place because it is STUNNING. Wonderful one day stay but goodness so worth it!

Don't skip over this perfect spot. One thing I loved most was that even though it is dog friendly nothing in the place smelled like dogs or had any odor. There were no stains on furniture. It was also perfectly cleaned. The beds were comfortable the bathrooms were spacious. We loved the back patio facing the trees. It was also a nice patio with only a few steps down to ground to make it easy to let the dogs out. The pull out couch was comfortable. I would stay again and again here. I've stayed several places in wintergreen and this cozy place and great location can't be beat!

This was a getaway to see our kids, and it was perfect. Amanda went out of her way to accommodate our needs, and her place is a great refuge. What really stands out is how communicative she was in every step from booking, to questions, checkin, and checkout. Everything went super smoothly and we enjoyed our stay.

This place was great for my family to go snowboarding. Conveniently located to wintergreen resort. The owners are great town to with and place was very clean.

There was a small issue with the check in process but it was not the fault of the host. He was very responsive and helpful. We had a fantastic time!!

This was our first time staying on Eagles Swoop and it was awesome. This is a great bottom floor end unit, so it was easy to ski right off the deck - really could not have been any closer to the slopes. Still felt private, close to the Market and the Mountain Inn - just a great location. The condo itself was great. The kitchen is small but was one of the best stocked kitchens we've ever stayed at. The owners have thought of everything throughout the condo and all the updates were great. We would absolutely stay here again. Thanks!

The place was perfect, we had a group of 4 and it fit us all very comfortably, and it was so nice being very close to the mountain. This is an absolutely fantastic option for those looking to ski/snowboard at Wintergreen and I heavily recommend it.

After my first reservation unexpectedly fell through, Jan's immediate response to have the same week available was really appreciated. The Summit views are the best of all of Massanutten, as I have stayed in several different units over the years. And, our upper unit had zero stairs from parking lot to unit door. I highly recommend booking the Summit with Jan!

My family and I definitely enjoyed our stay. This was our 5 year anniversary Christmas at massunutten and the location did not disappoint anyone. We enjoyed being on the mountain watching the skiers go up and come down the slopes. The kids enjoyed being close to all the snow activities. We are looking forward to rebooking and going back during the summer once all the new add-ons are done. Thank you Daniel