Condo holiday rentals in Charlottesville

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.

4.9 out of 5 average rating, 196 reviews

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.

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.

4.99 out of 5 average rating, 260 reviews

Sunset Vista Villa, Mountain Views-Close to Slopes

Welcome to Sunset Vista Villa, Mountain Views & Close to Slopes (on the shuttle route) This beautiful, 2 bedroom, 2 bath, first-floor-unit with top story mountain views, is near all amenities the Wintergreen Resort has to offer. It comfortably sleeps five and with its western vistas, sunsets are a thing to behold! Whether you spend your days hiking, skiing or enjoying the wineries and breweries, SVV will enhance your stay. Book today & come enjoy the Wintergreen Resort and Blue Ridge Mountains!

A spacious great room is featured, furnished with a comfortable brown leather sofa and accent chairs. Large panoramic windows provide expansive views of the Blue Ridge Mountains, while a dining area with a table for six is positioned nearby. Warm wood flooring enhances the inviting space.

4.98 out of 5 average rating, 123 reviews

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.

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.

4.97 out of 5 average rating, 118 reviews

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!

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.

4.93 out of 5 average rating, 239 reviews

The Modern Mountain Condo

Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

4.9 out of 5 average rating, 146 reviews

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.

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 158 reviews

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

4.96 out of 5 average rating, 165 reviews

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.

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.

4.97 out of 5 average rating, 146 reviews

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!

4.97 out of 5 average rating, 120 reviews

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!

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.

4.97 out of 5 average rating, 107 reviews

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

Forget your worries in this spacious and serene space. Condo has been completely renovated and can be enjoyed all year round! Located between the Wintergarden Spa, the Nature Foundation and the Devils Knob Sports Center (golf, tennis and fine dining restaurant) Stone Ridge neighborhood is centrally positioned to most of the Resort amenities. 5 min drive to slopes 5 mins to Market 15 to Devils Backbone 3 mins to Devils Knob golf course

A cozy living room is presented, featuring two plush leather sofas, a coffee table, and a fireplace. Natural light enters through large windows, and decorative accents enhance the warm ambiance. A flat-screen TV sits on a stand, completing the inviting space.

4.98 out of 5 average rating, 194 reviews

Cozy getaway with heated floors

Step into a beautifully crafted retreat where a stunning live-edge oak breakfast bar with leather stools awaits. Enjoy the elegance of granite countertops and sleek stainless steel appliances. The cozy living room, with its plush leather sofas and a warm fireplace, offers the perfect spot to relax. Accommodating up to 2 guests, you'll find a luxurious queen bed. Radiant heated floors add an extra touch of comfort throughout your stay.

Popular amenities for Charlottesville condo rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.9 out of 5 average rating, 29 reviews

A bright living area features a comfortable gray sectional sofa and various seating options, including a patterned chair. A large flat-screen TV is mounted above a black fireplace, with daylight filtering through expansive windows that showcase views of surrounding nature.

Condo in Massies Mill

Mountain Top Getaway

Superhost

A spacious living area is highlighted by large glass sliding doors that provide access to a deck. Cozy seating options include an armchair and a comfortable couch, with natural light illuminating the space. A decorative rug and a stylish coffee table add to the inviting ambiance.

Condo in Belmont

4.53 out of 5 average rating, 58 reviews

Downtown C'ville Luxury w/ Rooftop + Common House

An open dining area features a large wooden table surrounded by leather chairs. A granite countertop separates the dining space from the kitchen. Light fixtures cast soft patterns on the ceiling, while large windows provide views of the surrounding greenery.

4.9 out of 5 average rating, 31 reviews

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

A patio area features a round table surrounded by four metal chairs, offering a clear view of the expansive landscape. The sky displays vibrant hues of orange and pink as the sun sets over the distant mountains, creating a serene backdrop.

4.98 out of 5 average rating, 42 reviews

Breathtaking Views from The Ledges

A balcony view captures a serene sunset over snow-covered mountains, with hues of orange and purple in the sky. String lights adorn the railing, and a warm beverage is held in one hand, creating a peaceful ambiance.

5 out of 5 average rating, 38 reviews

Spacious Ski In Ski Out Condo with Mountain View

The living area features a large sectional sofa facing a stone fireplace, with a wooden accent wall above. Floor-to-ceiling windows provide expansive views of the surrounding forest and mountains. A dining table and four chairs sit nearby, with stylish decor enhancing the inviting atmosphere.

5 out of 5 average rating, 34 reviews

Lovely Ski Front Private 3-bed/3-bath condo

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.

4.97 out of 5 average rating, 29 reviews

Recently updated - views of the Blue Ridge Mtns

4.92 out of 5 average rating, 73 reviews

The living room features a spacious sectional sofa and two armchairs, arranged around a wooden coffee table. A wood-burning fireplace is located against a green wall, complemented by softly illuminated shelves. Natural light filters through windows, creating a cozy atmosphere.

Condo in Roseland

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

Pet-friendly condo rentals

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.

4.95 out of 5 average rating, 140 reviews

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

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.

4.95 out of 5 average rating, 331 reviews

Five Minute Walk to Everything!

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.

4.94 out of 5 average rating, 240 reviews

Eight Minute Walk to Everything

A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.

4.94 out of 5 average rating, 17 reviews

Condo with Valley Views!

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.

4.89 out of 5 average rating, 117 reviews

1720 High Ridge at Wintergreen Resort

A cozy living room features comfortable seating on a sofa and armchair, complemented by a round coffee table. A smart TV is positioned above a fireplace with subtle artwork on the wall. Natural light filters through large windows, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 101 reviews

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

4.95 out of 5 average rating, 193 reviews

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

The living area features a spacious gray sectional couch with decorative pillows, a low wooden coffee table, and a patterned area rug. A wood-burning fireplace is situated against a white wall adorned with rustic decor. Natural light enters through large windows.

4.94 out of 5 average rating, 259 reviews

Cozy, clean, quiet mountain condo- King bed

Condo rentals with a pool

The exterior of the mountain condo is displayed, featuring a brown wooden structure with a steeply pitched roof. A wooden walkway leads to the entrance, bordered by low greenery. Large windows adorn the upper level, providing natural light. The setting is surrounded by trees, indicating a tranquil environment.

4.94 out of 5 average rating, 35 reviews

Pepper's Mountain Pad

A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.

4.9 out of 5 average rating, 121 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

A cozy living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by an accent chair. A fireplace is positioned against the wall, and large windows allow natural light to illuminate the space, overlooking lush greenery.

4.9 out of 5 average rating, 50 reviews

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

Two reclining chairs are positioned in a cozy living area, complemented by a warm orange wall. A dining area with a wooden table is visible in the background, along with large glass doors that provide natural light and access to a terrace overlooking greenery.

4.88 out of 5 average rating, 34 reviews

On the mountain, pet and child friendly

A spacious living area features a comfortable sofa, a wooden coffee table, and a well-lit dining space. Large windows allow natural light to fill the room, and a fireplace adds warmth. Colorful artwork adorns the walls, complementing the light-toned flooring.

4.91 out of 5 average rating, 58 reviews

Wintergreen! Dog friendly, cozy and comfortable

A view from the back deck showcases a snowy landscape with scattered trees. The blue sky provides a bright backdrop, and snow covers the ground, reflecting the sunlight. An Adirondack chair sits in the foreground, inviting guests to relax while enjoying the scenic surroundings.

4.96 out of 5 average rating, 83 reviews

Ski In/Out! Slope Side - Eagles Swoop!

5 out of 5 average rating, 6 reviews

A well-appointed bedroom features a spacious bed with decorative bedding and two bedside lamps. Natural light filters through a window adorned with drapes. A wooden desk and chair are positioned nearby, providing a functional workspace.

Condo in Massanutten

7 Day Vacation in Massanutten Resort, VA

The family room features a spacious, comfortable sofa arranged around a round wooden coffee table. Large windows allow natural light to fill the space, with views of the outdoors. A stack of firewood sits neatly beside the fireplace, and dining space is visible in the background.