
Condo vacation rentals in Charlottesville
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Top-rated condo rentals in Charlottesville
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Vacation rentals for every style
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Popular amenities for Charlottesville condo rentals
Weekly condo rentals

2 br/2 b condo; skiing; hiking; wineries; pool
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.

Massanutten Woodstone or Summit 4BR, 4BA
Daniel was great and our family of six really enjoyed our stay! It was a great deal and a great time!

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br
The place was super nice, honestly better than the pictures! Our group had a great time and all loved the place. Everything was super clean and organized. There was also a binder with local recommendations and we visited some of those restaurants and they were fantastic. I would definitely stay here again and recommend it to anyone.

Recently updated - view of the Blue Ridge Mtns
This condo was perfect for a long ski weekend for our family of 4. Located close to slopes, clean and with a spectacular view! Would definitely stay again!

Beautiful Mountain Getaway - Walk to Everything!
Beautiful and well stocked condo. Perfect location, we could walk to everything on our ski trip. Wonderful and hospitable hosts!

Wintergreen condo near Nature Foundation & Spa
We've stayed in a lot of condos in Wintergreen over the years, and this may be one of my favorites. This was a very comfortable two bedroom / two bathroom. It was a perfect size for our group of 2 adults and 2 teens. The furnishings were very nice. It is easy to get into (first floor). The view is of the woods behind the condo and quiet. Also, we appreciate how responsive the host was! She quickly returned our call in the evening when we had a little trouble getting into the lock code. Her instructions had been perfect; we just made a mistake with the code. We should have brought a little dishwashing detergent. There was one pod there. I'd stay there again.

Wintergreen Condo -Steps to Ski
Great condo in heart of wintergreen. Went there during a snow storm for skiing. Place was easy to find. Private entrance to community so no issues with parking. Condo is big enough for 5-6 people. Everything was clean. Vinay had a small welcome basket with snacks and hot chocolate pack which came in handy after full day of skiing in bitter cold. Walking distance to slops and nearby restaurants. Very comfortable beds. Everything in kitchen and laundry area worked perfectly. There is a ski closet outside the condo to store your gear. We will definitely be coming back and staying in this place on our next ski trip.

Mountain top 3-bedroom condo with spectacular view
Lovely relaxing long weekend looking at that view! Felt right at home in the condo. Appreciated that even though its dog-friendly, it's not a place that is covered in dog hair! The owners were very responsive to our questions, which we apprecaited. Would highly recommend!
Pet-friendly condo rentals

Mtn/Firework Views from Private Deck ~ King Suite
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!

1720 High Ridge at Wintergreen Resort
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)

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Cute 1 bedroom condo on top of the mountain at a ski resort. Would deff book again if looking for a place in area.

Best View in the Blue Ridge from Biscuit's Porch
View is even more beautiful in person! We loved the balcony. Kitchen had everything we needed to make meals at home. Our pup loved the place too!

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
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!

Nature’s Haven 1 Bedroom Condo Wintergreen Resort
Very lovely little home.

Cozy, clean, quiet mountain condo- King bed
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.

Vineyards, Views & Brews with 2 Floors
Owners great to work with and very responsive. Place is cozy with beautiful views, ideally located within Wintergreen. Highly recommend!
Condo rentals with a pool

Pepper's Mountain Pad
An amazing host that was quick to respond and had great communication. The place was neat and easy and super close to Wintergreen Resort! Would book again!

On the mountain, pet and child friendly
Good place, everything was as described. Overlooks the golf course.

Moutain Maison
Great one bedroom condo with cozy but spacious living room and bedroom. Best highlight is that it is about a 7 minute walk to the slopes and the small resort village for wintergreen. Perfect spot for a getaway.

The Perfect Getaway-Cozy Condo for 2 to 4
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.

Beautifulviews/WalktoResort&WTGMusicFest/PupsOK
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!

Happy hour on the 18th Hole
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.

7 Day Vacation in Massanutten Resort, VA
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!

The Perch in Wintergreen Laurelwood
We had a wonderful stay at Ashley’s place! The location was perfect for skiing. Ashley was very responsive - we would definitely stay here again!
Quick stats about condo rentals in Charlottesville
Total rentals
30 properties
Nightly prices starting at
$69 CAD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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- Massanutten Resort
- Luray Caverns
- Ash Lawn-Highland
- Chisholm Vineyards at Adventure Farm
- Lake Anna State Park
- Early Mountain Winery
- Prince Michel Winery
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