Condo vacation 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.

4.91 out of 5 average rating, 189 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.

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, 322 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, 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 master 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.

4.89 out of 5 average rating, 138 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 historic 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. Breakfast Included: oatmeal, keurig coffee, tea.

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, 121 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, 110 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!

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, 238 reviews

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.

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.

4.99 out of 5 average rating, 166 reviews

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

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, 254 reviews

Sunset Vista Mountain Views “Skies for Miles”

Welcome to Sunset Vista Villa, where you enjoy, “Skies for Miles.” This beautiful, 2 bedroom, 2 bath, first-floor-unit with second 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 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.

4.96 out of 5 average rating, 159 reviews

1 bedroom condo, hiking, breweries, wineries

Enjoy the mountains in the spring & summer enjoy hiking or a swim in the heapool! 1BR 1BA centrally located in Wintergreen 5 minute walk to Wintergreen resort Close to many hiking trails Enjoy the many breweries & wineries in the area Mountaintop Market is across the street 1 Bedroom 1 Bath & New queen sleeper sofa Stocked kitchen, cookware, spices & cooking oils Premium coffee & assorted tea Private furnished patio Wood burning fireplace, all you need for a quiet getaway

4.97 out of 5 average rating, 118 reviews

Mountaintop Overlook: Warm Fires • Golden Views

Breathe in the Crisp Air, Cozy Up by the Fire, Take in Golden Views. The Mountain Top Overlook @ Wintergreen Resort is a cozy and clean two bedroom(king size beds), two full bathroom condo with a living room sleeper sofa. This condo accommodates 6 guests. It boasts panoramic window views of the Blue Ridge Mountains, while being located in sought after Wintergreen Resort. Ground level with easy access off the deck to a grassy area overlooking the valley.

A living room features large windows showcasing a vibrant sunset over the mountains. A cozy sofa is set against the backdrop, complemented by a patterned throw pillow. A coffee table with various decor items is positioned in front of it, alongside a decorative table with plants.

4.98 out of 5 average rating, 128 reviews

Slope side+Panoramic Mountain Views!

Panoramic views over Diamond Hill Ski Slope and the Blue Ridge Mountains. 2 bedroom/2 bath condo. Walk to slopes, hiking trails, and restaurants. Master w/King bed and attached bath with jetted tub. 2nd bedroom hosts 2 bunks- Twins over Double beds. Hall bath with shower and tub. Living Room with sleeper sofa, TV, and wood burning fireplace, wood included! Gated parking lot. Breathtaking Mountain Views + walking distance to the Mountain Inn! Perfection!

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, 188 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

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.89 out of 5 average rating, 28 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

4.53 out of 5 average rating, 58 reviews

A spacious living area is highlighted by a contemporary sectional sofa with patterned cushions and a wooden coffee table. Natural light pours in through large windows, enhancing the open-plan layout that features a stylish staircase and flows into the kitchen area, creating a cozy yet modern atmosphere.

Condo in Belmont

Downtown C'ville Luxury w/ Rooftop + Common House

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.

4.91 out of 5 average rating, 32 reviews

On the mountain, pet and child friendly

A spacious living area features large windows that provide expansive views of the surrounding landscape. Comfortable seating includes a sectional couch and a reclining chair, arranged around a wooden coffee table. A sleek stone fireplace and a mounted television add to the contemporary decor.

4.94 out of 5 average rating, 31 reviews

Wintergreen Mountain Views - Diamond in the Slopes

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, 97 reviews

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

The living area features large windows allowing natural light to illuminate the space. A sectional sofa, leather chairs, and a coffee table are arranged around the wood-burning fireplace. A dining table with wooden chairs is visible, alongside a view of the outdoors through the sliding glass doors.

4.94 out of 5 average rating, 63 reviews

Sitting on the 18th fairway

A cozy living room features a comfortable seating arrangement with plush chairs and a sofa. Large windows allow natural light to fill the space, enhancing the view of the surrounding greenery. A coffee table is placed centrally, surrounded by decorative plants.

4.79 out of 5 average rating, 73 reviews

Wintergreen Best location,Arcades,king bed,2 room

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

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, 138 reviews

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

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, 143 reviews

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

A panoramic view of rolling mountains under a dramatic sky filled with clouds. Light filters through the clouds, illuminating sections of the landscape. Tree-covered hills stretch into the distance, showcasing varying shades of green and blue.

4.74 out of 5 average rating, 153 reviews

Mountain Views

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, 54 reviews

Wintergreen! Dog friendly, cozy and comfortable

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.

5 out of 5 average rating, 10 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, 114 reviews

1720 High Ridge at Wintergreen Resort

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.

4.96 out of 5 average rating, 23 reviews

Recently updated - views of the Blue Ridge Mtns

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, 256 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.

4.97 out of 5 average rating, 33 reviews

Pepper's Mountain Pad

5 out of 5 average rating, 3 reviews

Ski-in/out What-a-Mountain View Fireplace King Bed

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

4.99 out of 5 average rating, 79 reviews

Time To Get Away-Cozy Condo for 2 to 4

A relaxed living room features a stone fireplace as a focal point, complemented by comfortable seating arrangements. A unique wall art piece adds character, while warm lighting creates a cozy ambiance. The floor showcases a wood and stone design, enhancing the inviting space.

4.96 out of 5 average rating, 81 reviews

BeautifulFallFoliage/Ski-In/Out/PupsWelcome!

A comfortable living area is presented, featuring a gray sectional sofa and an ottoman adorned with a decorative pattern. Natural light filters through multiple windows, illuminating the space. A small desk with two chairs is positioned nearby, with a fireplace adding to the cozy ambiance.

4.83 out of 5 average rating, 53 reviews

Happy hour on the 18th Hole

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.