Holiday rentals with a pool in Wintergreen Resort

A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.

4.98 out of 5 average rating, 206 reviews

Hottub Ski In/Ski Out Renovated Chalet Lower Tyro

Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

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, 327 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.

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, 122 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.

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, 171 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

4.98 out of 5 average rating, 208 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

4.96 out of 5 average rating, 113 reviews

Cliffs Edge- It's Pumpkin Spice Time!

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

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, 258 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 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, 155 reviews

2-min drive from 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 CLOSEDe

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, 164 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

Flat in Wintergreen Resort

A table set for two features a bottle of sparkling beverage and two glasses, accompanied by an elegant plate of appetizers. The backdrop showcases expansive mountain views under a bright sky, enhancing the serene atmosphere of the outdoor dining area.

4.97 out of 5 average rating, 105 reviews

Mountain View Nest

From the moment you walk in, this condo offers endless opportunities to relax and retreat. The sweeping mountain views over the back deck provide the ideal setting for a romantic getaway, a girls weekend, or much needed time to recharge. This one bedroom/bathroom unit with a king sized bed, fully stocked kitchen, and artistic decor is located on the third floor of the Ledges. It is the perfect location for those who ski, hike, golf, or taste the flavors from local wineries.

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, 144 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, 119 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.

Popular amenities for Wintergreen Resort rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a stone fireplace as the focal point, framed by large windows that offer views of the surrounding trees. A comfortable sectional sofa is arranged around a coffee table, with a television positioned on a media console to the side.

4.96 out of 5 average rating, 106 reviews

Cozy 5-bedroom home for large gatherings.

4.93 out of 5 average rating, 232 reviews

The exterior of Pine Lake Lodge is displayed, featuring a stone chimney and a covered porch with several chairs. Lush green grass surrounds the lodge, complemented by trees and colorful foliage in the background, creating a serene outdoor setting.

Home in Charlottesville

Pine Lake Lodge

The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.

4.89 out of 5 average rating, 141 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

4.96 out of 5 average rating, 223 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Heated Covered Private Pool / Hot Tub

A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.

4.96 out of 5 average rating, 112 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.

4.95 out of 5 average rating, 130 reviews

Bear's Mountain Escape

Superhost

A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. The serene view of the mountains is visible in the distance, complementing the tranquil setting. Steps lead to the hot tub, creating easy access.

4.81 out of 5 average rating, 162 reviews

Misty Mountain Cabin w/spa

A modern mountain home is showcased amidst a snowy landscape, surrounded by trees. A deck extends from the front entrance, providing views of the valley below. Soft white snow covers the ground, complementing the neutral tones of the house.

4.82 out of 5 average rating, 114 reviews

5 min toSki! Mntn View HotTub Pool Table MovieRoom

Apartment rentals with a 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, 57 reviews

Wintergreen! Dog friendly, cozy and comfortable

An outdoor deck features a comfortable seating area with plush cushions and a coffee table. Two glasses of wine rest atop the table, surrounded by panoramic views of the Blue Ridge Mountains bathed in soft hues of sunset.

5 out of 5 average rating, 47 reviews

Buena Vista Panoramic Retreat: Million Dollar View

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, 27 reviews

Recently updated - views of the Blue Ridge Mtns

4.99 out of 5 average rating, 79 reviews

Time To Get Away-Cozy Condo for 2 to 4

A spacious bed is dressed in plaid and textured bedding, accompanied by a decorative fern in a ceramic pot on a wooden nightstand. Soft lighting illuminates the serene atmosphere, enhancing the restful setting.

4.93 out of 5 average rating, 75 reviews

Walkoff Deck + 2 Fireplaces & Magical Views

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

SlopeSide/Ski-In/Ski-Out/PupWelcome!

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.

4.95 out of 5 average rating, 38 reviews

Love of mountains oh fill my cup

Other holiday rentals with a pool

An outdoor deck is equipped with a propane firepit surrounded by a dark block, offering a cozy gathering space. Comfortable, upholstered seating is arranged for relaxation, with expansive views of trees and hills in the background, showcasing the natural beauty of the mountainous landscape.

4.98 out of 5 average rating, 43 reviews

Stunning Views, Hot Tub, Impeccable Design

4.94 out of 5 average rating, 33 reviews

A warm and inviting living space features a stone fireplace with a fire glowing inside. A comfortable chair with patterned fabric sits beside a small glass coffee table. Natural light enters through large windows, creating a cozy atmosphere.

Home in Roseland

Hot Tub! Wintergreen Resort!

An outdoor deck features a cozy fire pit surrounded by comfortable seating. The scene is tranquil with trees in the background, and a colorful sunset sky enhances the atmosphere. Soft lighting along the railing adds a welcoming touch.

5 out of 5 average rating, 36 reviews

4.93 out of 5 average rating, 14 reviews

Home in Roseland

Mountain Views, Hot Tub, Impeccable Design

A spacious outdoor living area features a modern hot tub with glowing blue water, surrounded by a custom-built bar. Soft lighting from overhead lanterns adds a cozy ambiance, while a large screen TV is mounted nearby, overlooking the tranquil wooded surroundings.

5 out of 5 average rating, 44 reviews

Luxury Oasis|Family&Pets|Outdoor Lounge|Fire pit

The exterior of the house features a modern design with a combination of gray siding and a shingled roof. Surrounded by trees, the entryway is framed by steps leading to the front door, with a spacious driveway visible in the foreground.

4.9 out of 5 average rating, 58 reviews

Luxury House on Mountain Golf Course near Slopes

Flat in Wintergreen Resort

A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.

5 out of 5 average rating, 11 reviews

Family and dog friendly with views and pools!