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Condo vacation rentals in Charlottesville

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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 €52 per night before taxes and fees

  • Verified guest reviews

    Over 1,000 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!

Top-rated condo rentals in Charlottesville

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Superhost
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Condo in Wintergreen Resort

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

4.88 out of 5 average rating, 223 reviews
Top guest favorite
Condo in Wintergreen Resort

Extremely private, HOA pool/stair-free entry

Extremely private, 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 OPEN for season

4.97 out of 5 average rating, 180 reviews
Top guest favorite
A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.
Condo in Wintergreen Resort

Where the Trail Ends

Some trips are about doing everything. This one’s about slowing down. Nestled inside Wintergreen Resort, this updated mountain retreat puts hiking trails, ski slopes, wineries, and breweries at your door - then gives you a warm space to come home to. Curl up by the fireplace, cook a real meal in a full kitchen, or take the morning slow on your private patio with mountain views. When you’re ready to explore, everything is close. When you’re not, the community pool and quiet will keep you busy.

4.93 out of 5 average rating, 255 reviews
Top guest favorite
The living area features large sliding glass doors that open to a stunning view of the mountains. A modern dining table is positioned nearby, illuminated by a pendant light. Comfortable seating is arranged around the room, enhancing the inviting atmosphere.
Condo in Wintergreen Resort

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!

4.98 out of 5 average rating, 133 reviews
Top guest favorite
A bright bedroom features a spacious bed flanked by two bedside tables with lamps. A framed cityscape artwork adorns the wall above the bed. Dark curtains frame the window, and a patterned rug covers the hardwood floor, creating a cozy yet modern ambiance.
Condo in North Downtown

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.

4.92 out of 5 average rating, 201 reviews
Top guest favorite
A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.
Condo in Wintergreen Resort

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

4.99 out of 5 average rating, 185 reviews
Top guest favorite
The main living area features a new sectional sofa facing a stone fireplace with a mounted TV above. A coffee table is positioned centrally, while light fills the room through large windows. The space is designed with soft carpeting and built-in shelving.
Condo in Wintergreen Resort

Beautiful Mountain Getaway - Walk to Everything!

This beautifully renovated 3 BR / 2 BA mountain condo is very centrally located in the main Wintergreen village - steps from the Mountain Inn, ski slopes, restaurants and trails. The corner unit is at the end of the building (closest to the slopes) which means it gets a ton of natural light! All of the furniture is brand new including the sectional sofa in the living area. The place comes fully stocked with everything you need and includes outdoor storage for any gear & equipment.

4.97 out of 5 average rating, 100 reviews
Superhost
A private furnished patio features a cozy seating area with light-colored cushions on a dark frame sofa. A wooden coffee table sits in front, accented by a woven rug. The surrounding greenery adds a natural backdrop, creating a peaceful setting for relaxation.
Condo in Wintergreen Resort

1 bedroom condo, close to hikes & breweries & pool

Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors 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 or cool off in the heated community pool.

4.92 out of 5 average rating, 216 reviews
Top guest favorite
An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.
Condo in Wintergreen Resort

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

Come experience four seasons of fun- hit the ski slopes, hike the blue ridge mountains, enjoy local cider or beer, or cozy up by the fire and enjoy the mountain views. Located across the street from the aquatic/fitness center & spa, on the Devil's Knob golf course, and next to the ski shuttle pickup location and Nature Foundation, the location couldn't be better. The unit has a spectacular sunset view from the balcony, a gas fireplace, and speedy wifi for working or streaming!

4.95 out of 5 average rating, 156 reviews
Guest favorite
Condo in Wintergreen Resort

Cozy Comfort with a View - Wintergreen Resort

Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.

4.91 out of 5 average rating, 166 reviews
Superhost
Condo in Staunton

Third & Thornrose, Staunton Condominium

Our guests stay upstairs in our 1929 American Foursquare house. Central air; separate entrance, wooden floors. Daily, weekly or monthly rates. Small, fully-equipped kitchen with stove and refrigerator, small dining room. The bathroom has a tub and shower. Television with Netflix. Wifi and off-street parking. Two bedrooms (queen-sized bed, two XL twin beds), living room. Short walk to Gypsy Hill Park, 1 mile to historic downtown (Trolley). Small town, Big Magic!

4.82 out of 5 average rating, 472 reviews
Top guest favorite
A glass of white wine is positioned in the foreground, capturing the warm hues of a sunset. The sun's golden rays reflect off the wine, while silhouettes of trees and distant mountains create a tranquil backdrop in the evening sky.
Condo in Wintergreen Resort

Panoramic Sunsets Mountain Views Pool $99 Midweek

SUMMER SPECIAL! Stay 2 nights and get your 3rd night for just $99 when you check in Sunday–Wednesday (select stays, next 60 days). Escape the summer heat and enjoy cooler mountain temperatures, central A/C, a heated outdoor pool, breathtaking sunset views, and two king suites with private en-suite bathrooms. Summer dates are filling fast—book now and experience one of Wintergreen's most sought-after mountain-view condos.

4.99 out of 5 average rating, 275 reviews

Popular amenities for Charlottesville condo rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly condo rentals

Top guest favorite
A cozy living area features a blue couch facing a wood-burning fireplace, with a flat-screen TV mounted above. A side chair provides additional seating. Natural light filters through large windows, illuminating a small coffee table adorned with a vase of yellow tulips.
Condo in Wintergreen Resort

Cozy Laurelwood condo - 1 min walk to pool

5.0 out of 5 average rating, 104 reviews
Guest favorite
Condo in Wintergreen Resort

Panoramic Peak: Wintergreen Condo with Views

4.9 out of 5 average rating, 155 reviews
Top guest favorite
A living room features a stone fireplace with a wooden mantel. A clock is mounted above, and decorative items are displayed on the mantel. Hardwood flooring complements the room's layout. The space is open to a kitchen area, visible in the background, with light cabinets and appliances.
Condo in Wintergreen Resort

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

4.96 out of 5 average rating, 127 reviews
Superhost
A wooden staircase is flanked by trees, leading to a brown wooden building with a triangular roof. Large windows allow natural light to enter, surrounded by a peaceful forested area.
Condo in Wintergreen Resort

Cozy Condo - Sleeps 4

4.78 out of 5 average rating, 106 reviews
Guest favorite
A serene landscape captures the sun setting behind distant mountains, surrounded by an expanse of trees and valleys. Soft rays of light break through the clouds, illuminating the sky with warm, golden hues. The atmosphere presents a peaceful retreat into nature.
Condo in Wintergreen Resort

Wander Lodge: Golf, Spa, Wine, or just a getaway

4.87 out of 5 average rating, 182 reviews
Top guest favorite
A cozy living area features a brown sofa and an armchair in muted blue. A wooden coffee table sits atop a light brown rug, with a lamp illuminating one corner. Framed artwork adorns the walls, while a storage cabinet offers practical space.
Condo in Wintergreen Resort

Cozy Updated Wintergreen Condo at Devil’s Knob

4.94 out of 5 average rating, 167 reviews
Top guest favorite
A light-filled living area features a spacious sectional sofa paired with two side chairs. A wooden coffee table is centrally positioned on a soft area rug. Large sliding doors lead to an exterior space, while a smart TV is mounted against the wall.
Condo in Bridgewater

3 BR, 3 bath, BWC, EMU, JMU, 1-81 *WIFI* Buc-ee’s

4.98 out of 5 average rating, 152 reviews
Top guest favorite
A cozy living area features a light-colored sofa and an accent chair positioned around a round, woven coffee table. A textured area rug adds warmth to the space, while a stacked stone fireplace serves as a focal point, complemented by tall windows allowing natural light.
Condo in Wintergreen Resort

Base Camp Condo

4.98 out of 5 average rating, 110 reviews

Pet-friendly condo rentals

Guest favorite
A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.
Condo in Wintergreen Resort

Ski-In Ski-Out ~ Mtn Views ~ King Suite

4.95 out of 5 average rating, 180 reviews
Guest favorite
A spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.
Condo in Wintergreen Resort

BlueRidge Getaway- Dog Friendly

4.93 out of 5 average rating, 197 reviews
Guest favorite
The exterior view captures a two-story mountain condo, featuring a welcoming wooden ramp leading to a deck. The brown wood siding complements the natural surroundings, and multiple windows allow for ample light. Seasonal decor embellishes the entry, enhancing the inviting facade.
Condo in Wintergreen Resort

Your Cozy Mountain Getaway Awaits

4.8 out of 5 average rating, 109 reviews
Top guest favorite
The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.
Condo in Wintergreen Resort

Eight Minute Walk to Everything

4.94 out of 5 average rating, 254 reviews
Top guest favorite
The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.
Condo in Wintergreen Resort

Five Minute Walk to Everything!

4.96 out of 5 average rating, 362 reviews
Guest favorite
A comfortable living area features a spacious gray sofa and a wooden coffee table, positioned on a patterned rug. Light from a nearby lamp and large sliding doors illuminates the space, which offers views of the outdoors. A cozy accent chair completes the inviting setup.
Condo in Wintergreen Resort

New Construction! 1 Bed/2 Bath, pet friendly

4.96 out of 5 average rating, 230 reviews
Guest favorite
The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.
Condo in Wintergreen Resort

1720 High Ridge at Wintergreen Resort

4.89 out of 5 average rating, 127 reviews
Top guest favorite
Condo in Wintergreen Resort

Cozy, clean, quiet mountain condo- King bed

4.94 out of 5 average rating, 263 reviews

Condo rentals with a pool

Guest favorite
A series of ski gondolas are seen ascending a mountain, suspended from overhead cables. Snow-covered slopes can be observed below, with a bright blue sky providing a clear backdrop. The gondolas feature large windows, allowing views of the winter landscape.
Condo in McGaheysville

Massanutten Woodstone 2-BR, 2 Bath

4.84 out of 5 average rating, 147 reviews
Top guest favorite
The spacious living area features a stone fireplace and large windows that allow natural light. A comfortable sofa faces the cozy seating area, while a dining table accommodates several guests. An artwork piece complements the warm decor, enhancing the inviting space.
Condo in Wintergreen Resort

WonderfulViews/FallFoliage/Hiking/SpaciousCondo

4.98 out of 5 average rating, 54 reviews
Guest favorite
A balcony view features a round table surrounded by four metal chairs. The railing, designed with geometric patterns, overlooks a lush landscape filled with trees. Soft sunlight filters through the foliage, creating a serene outdoor ambiance.
Condo in Wintergreen Resort

A Scenic Mountain Retreat, your Home on the Ridge

4.97 out of 5 average rating, 59 reviews
Top guest favorite
A cozy living area features a stone fireplace with a wooden mantle. Natural light enters through large windows framed by light curtains. Comfortable seating includes a brown sofa with decorative pillows and a stylish orange chair. An adjacent dining table offers space for meals.
Condo in Wintergreen Resort

3 Ridges 3 min walk to slopes,besides inn,King bed

5.0 out of 5 average rating, 29 reviews
Top guest favorite
A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.
Condo in Wintergreen Resort

Recently updated - views of the Blue Ridge Mtns

4.97 out of 5 average rating, 35 reviews
Top guest favorite
A sunset view is captured over the mountains, with the sun dipping below the horizon, casting warm hues across the sky. Dense trees frame the scene, providing a sense of tranquility amid the natural landscape.
Condo in Wintergreen Resort

Love of mountains oh fill my cup

4.95 out of 5 average rating, 56 reviews
Top guest favorite
Condo in Wintergreen Resort

Guest-Favorite Views, 2 Decks + Dog Retreat

4.94 out of 5 average rating, 87 reviews
Guest favorite
Condo in Wintergreen Resort

Walk to Ski Slopes and Hiking Trails | Wintergreen

4.88 out of 5 average rating, 8 reviews

When is the best time to visit Charlottesville?

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