
Condo vacation rentals in Charlottesville
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Top-rated condo rentals in Charlottesville
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2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Luxury Condo in the Sky! Finest in Wintergreen!
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

Stylish*Updated*Central*Walk to Slopes*Dogs OK!
Step into the allure of our fantastic Wintergreen, just a leisurely 4min stroll away from the heart of Wintergreen's mtn action! Tucked away in a serene and tranquil nook of the mountain, our meticulously curated property combines serene relaxation with unfettered access to the thrilling outdoor adventures that await nearby. The closest hiking trail is within 200 yds! Whether you're a couple seeking a romantic retreat or a small, fun family, our home is eager to embrace your mountain dreams!

The Townie 3 BD/2BA Historic Downtown Building
Three bedroom/ two bathroom apartment in a 1940s building located in the heart of Charlottesville, just off the Downtown Mall. Brightly lit large space with charm and comfort, including full kitchen, wifi, living room w/ smart TV, hardwood floors throughout, blackout curtains, laundry in unit. Your group will enjoy easy access to everything - walk score 100! Three queen beds + living room sofa + air mattress. Pet friendly with extra fee. Each bedroom has blackout curtains for comfort.

2-min drive to slopes, stair-free/free firewood!
Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

Eight Minute Walk to Everything
This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

3 BR 3 BA, 2 story condo in Highlands
Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

Ski-In Ski-Out ~ Mtn Views ~ King Suite
Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

Mountain View Condo at Wintergreen, Fireplace
Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Cozy Condo - Sleeps 4
A wonderful weekend escape no matter the time of year. Condo has been completely renovated in the heart of Wintergreen Resort. Fully equipped condo for guests to come and enjoy the slopes. Within walking distance to the ski lift and all the amenities that the area has to offer. We are the only condo complex that also has a pool it's own pool for condo owners only. **the pool is for the condo complex and is shared with the other units.
Popular amenities for Charlottesville condo rentals
Weekly condo rentals

Mountain Top Getaway

Downtown C'ville Luxury w/ Rooftop + Common House

Condo w/ Full Kitchen, Balcony, King & Queen Beds

Buena Vista Panoramic Retreat: Million Dollar View

Sitting on the 18th fairway

Spacious Ski In Ski Out Condo with Mountain View

Mountain View Vista: Resort Condo w/ Views

Love of mountains oh fill my cup
Pet-friendly condo rentals

All-Season 2bd/2ba next to Spa view of Golf Course

Mountain Views

Wintergreen! Dog friendly, cozy and comfortable

Condo with Valley Views!

1720 High Ridge at Wintergreen Resort

Tips Up: Cozy Slopeside Retreat w/ Fireplace

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

Cozy, clean, quiet mountain condo- King bed
Condo rentals with a pool

On the mountain, pet and child friendly

Wintergreen Ski Retreat, Cozy Condo Near Slopes

Timbers Lodge 39 with Wintergreen Advantage

Recently updated - views of the Blue Ridge Mtns

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

A Mountain Escape-Cozy Condo for 2 to 4

Slope Views, Aspen Suite — 2 Fireplaces

Ski In/Out! Slope Side - Eagles Swoop!
When is the best time to visit Charlottesville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ378 | ﺩ.ﺇ393 | ﺩ.ﺇ470 | ﺩ.ﺇ470 | ﺩ.ﺇ477 | ﺩ.ﺇ470 | ﺩ.ﺇ463 | ﺩ.ﺇ470 | ﺩ.ﺇ558 | ﺩ.ﺇ470 | ﺩ.ﺇ496 | ﺩ.ﺇ470 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about condo rentals in Charlottesville

Total vacation rentals
Explore 30 vacation rentals in Charlottesville

Nightly prices starting at
Charlottesville vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 1,090 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Charlottesville vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Charlottesville rentals

4.8 Average rating
Charlottesville stays are highly rated by guests—averaging 4.8 out of 5!
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- Shenandoah National Park
- Luray Caverns
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Lake Anna State Park
- Frontier Culture Museum
- Prince Michel Winery
- Blenheim Vineyards
- Wintergreen Resort
- Shenandoah Caverns
- Cardinal Point Winery
- Glass House Winery
- James Madison University
- Devils Backbone Brewing Co Basecamp
- University of Virginia
- Monticello
- John Paul Jones Arena
- White Lotus Eco Spa Retreat
- The Rotunda
- Grand Caverns
- Cooter's Place
- IX Art Park
- James River State Park




