Condo vacation rentals in Charlottesville

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Popular amenities for Charlottesville condo rentals

Weekly condo rentals

Guest favourite
Condo in Wintergreen Resort
4.9 out of 5 average rating, 48 reviews

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

JamesRating, 5 stars2 months ago
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.
Superhost
Condo in Massanutten
4.84 out of 5 average rating, 25 reviews

Massanutten Woodstone or Summit 4BR, 4BA

HeatherRating, 5 stars3 months ago
Daniel was great and our family of six really enjoyed our stay! It was a great deal and a great time!
Top guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 87 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

MackenzieRating, 5 stars1 week ago
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.
Guest favourite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 19 reviews

Recently updated - view of the Blue Ridge Mtns

JenniferRating, 5 stars3 months ago
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!
Guest favourite
Condo in Wintergreen Resort
4.97 out of 5 average rating, 86 reviews

Beautiful Mountain Getaway - Walk to Everything!

RachelRating, 5 stars2 months ago
Beautiful and well stocked condo. Perfect location, we could walk to everything on our ski trip. Wonderful and hospitable hosts!
Guest favourite
Condo in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Wintergreen condo near Nature Foundation & Spa

CourtneyRating, 5 stars2 months ago
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.
Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 28 reviews

Wintergreen Condo -Steps to Ski

DeepakRating, 5 stars2 months ago
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.
Guest favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 97 reviews

Mountain top 3-bedroom condo with spectacular view

JimRating, 5 stars2 weeks ago
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

Top guest favourite
Condo in Wintergreen Resort
4.97 out of 5 average rating, 126 reviews

Mtn/Firework Views from Private Deck ~ King Suite

AlyssaRating, 5 stars3 weeks ago
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!
Guest favourite
Condo in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

HuntRating, 5 stars1 month ago
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)
Guest favourite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 166 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

DennisRating, 5 stars1 week ago
Cute 1 bedroom condo on top of the mountain at a ski resort. Would deff book again if looking for a place in area.
Top guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 228 reviews

Best View in the Blue Ridge from Biscuit's Porch

CassandraRating, 5 stars1 month ago
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!
Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 178 reviews

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

TimRating, 5 stars1 month ago
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!
Guest favourite
Condo in Roseland
4.9 out of 5 average rating, 60 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

KevinRating, 5 stars2 weeks ago
Very lovely little home.
Top guest favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars1 week ago
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.
Guest favourite
Condo in Wintergreen Resort
4.92 out of 5 average rating, 60 reviews

Vineyards, Views & Brews with 2 Floors

GinaRating, 5 stars2 months ago
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

Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 28 reviews

Pepper's Mountain Pad

KateRating, 5 stars2 months ago
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!
Guest favourite
Condo in Wintergreen Resort
5 out of 5 average rating, 18 reviews

On the mountain, pet and child friendly

ChrisRating, 5 stars3 weeks ago
Good place, everything was as described. Overlooks the golf course.
Top guest favourite
Condo in Wintergreen Resort
5 out of 5 average rating, 15 reviews

Moutain Maison

MargalitRating, 5 stars2 months ago
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.
Top guest favourite
Condo in Wintergreen Resort
4.99 out of 5 average rating, 73 reviews

The Perfect Getaway-Cozy Condo for 2 to 4

JefferyRating, 5 stars1 month ago
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.
Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 77 reviews

Beautifulviews/WalktoResort&WTGMusicFest/PupsOK

CarrieRating, 5 stars2 months ago
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!
Guest favourite
Condo in Wintergreen Resort
4.84 out of 5 average rating, 50 reviews

Happy hour on the 18th Hole

KevinRating, 5 stars1 month ago
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.
Top guest favourite
Condo in Massanutten
5 out of 5 average rating, 5 reviews

7 Day Vacation in Massanutten Resort, VA

MargieRating, 5 stars14 months ago
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!
Top guest favourite
Condo in Wintergreen Resort
5 out of 5 average rating, 39 reviews

The Perch in Wintergreen Laurelwood

BoscoRating, 5 stars1 month ago
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

Destinations to explore