Vacation rentals with a pool in Wintergreen Resort

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, 181 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.

Home 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, 201 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.

A serene outdoor space is showcased, featuring a swimming pool surrounded by lush greenery and lush trees. The pool is framed by a patio area, with wooden fencing that adds a layer of privacy. Natural light filters through the leaves, creating a peaceful atmosphere.

4.95 out of 5 average rating, 307 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.

Home in Wintergreen Resort

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, 109 reviews

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

Charming 3-bedroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a new gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level

A community pool is surrounded by lush greenery and well-maintained landscaping. Sun loungers are arranged alongside the pool, inviting relaxation. The area is serene, with a backdrop of trees, providing a quiet setting for guests to unwind.

4.93 out of 5 average rating, 230 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.

An outdoor pool is surrounded by a spacious deck with multiple lounge chairs. A shaded area with umbrellas provides comfort, while trees line the background, offering a natural setting. A slide structure is visible nearby, enhancing the recreational appeal of the area.

4.99 out of 5 average rating, 163 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

Home in Wintergreen Resort

A panoramic view of rolling mountains is framed by lush green treetops. Soft mist blankets the valleys below, gently illuminated by the sunlight above. The vibrant sky showcases clear blue hues with wisps of clouds, creating a serene and peaceful atmosphere.

4.96 out of 5 average rating, 107 reviews

Cliffs Edge- Hike, Play & Splash into Summer!

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.

5 out of 5 average rating, 245 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.

4.95 out of 5 average rating, 151 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

An open living area features a comfortable sofa with decorative pillows and a coffee table. A dining counter with tall stools is visible, alongside a well-equipped kitchen that includes a refrigerator and microwave. Wall art complements the muted tones of the room.

4.9 out of 5 average rating, 145 reviews

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.

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.

4.96 out of 5 average rating, 137 reviews

Mtn/Firework Views from Private Deck ~ 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!

A modern living room features a sleek stone fireplace with a wood mantel and a mounted television above. A cozy fire burns in the fireplace. A large coffee table made of natural wood rests in front, with decorative items placed on it. Natural light streams through nearby windows.