Vacation rentals with a pool in Wintergreen Resort

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Top-rated rentals with a pool in Wintergreen Resort

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A well-maintained patio surrounds a bright swimming pool featuring a water slide. The cottage's light-colored exterior and large windows are visible in the background, framed by lush landscaping and trees. Lounge chairs are set near the pool for relaxation.

Cottage in Charlottesville

4.86 out of 5 average rating, 80 reviews

Ridgeview Cottage: Mtn Views and Summer Pool!

This luxury cottage is perfectly situated between Charlottesville and VA wine country on a scenic by-way, offering 4 acres of impressive fall foliage and sweeping mountain views, grill, fire pit, and summer pool access. Located 5 miles from Foxfield and 20 minutes to UVA. Ideal for couples, but can easily accommodate two couples or a small family-- this location offers the best of both; a rural setting with outdoor amenities, yet a short drive to restaurants, shops, breweries, grounds and more.

Top guest favorite

A serene swimming pool is bordered by a partially covered patio featuring a seating area with comfortable furniture. Lush greenery and distant hills are visible in the background, enhancing the peaceful ambiance of the outdoor space.

Guesthouse in Afton

5 out of 5 average rating, 254 reviews

Mountain Cottage, Pool , Views, Wine / Brew Trail

Wake to gorgeous Mountain views & rolling green meadows bordering the Rockfish River on our family estate. Private attached unit with built in pool (mid April-mid Sept)in the Blue Ridge mountains of Nelson County Virginia on the center of the 151 Brew Ridge Trail. Much preparation has gone into making your stay beautiful, convenient and comfy. No need to physically interact if that’s your desire. Enjoy swimming, hiking, kayaking, horse back riding, skiing, snowboarding, and more! 3 nite minimum

Superhost

Home in Wintergreen Resort

4.79 out of 5 average rating, 101 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

Sweeping views year round. Contemporary décor with rustic style. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and hiking. 5min drive to slopes. ★3,500sqft on 3 floors ★Hot tub for 8 people ★Sound system ★2-Story vaulted ceiling, gas fireplace, 55” TV ★Movie room: 65” TV, pool table, wet bar, wine fridge ★Dining table seats 10 ★Desk and FAST WiFi ★Roku TV in every bedroom ★Park 6 cars Seasonal outdoor pool/tennis. Resort access not included.

Top guest favorite

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.

Condo in Wintergreen Resort

4.96 out of 5 average rating, 292 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.

Top guest favorite

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.

Condo in Wintergreen Resort

4.97 out of 5 average rating, 119 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.

Top guest favorite

A shared outdoor pool is surrounded by a concrete patio with several lounge chairs. Lush greenery from trees provides a natural backdrop, and a wooden fence encloses the area. A storage shed is visible nearby, contributing to the functional space.

Home in Wintergreen Resort

4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

You're sure to have a blast at this incredible mountain condo! Condo is walking distance to the Wintergreen Resort Ski Lodge, Restaurants, The Market, and much more! This is the only condo neighborhood at Wintergreen that has it's own private outdoor pool. If you are up for a short drive down the mountain; check out the quality breweries, restaurants, distilleries, golf, and other fun activities near by! The Charlottesville area has been named 2023 Wine Region of the Year by Wine Enthusiast!

Superhost

A seasonal pool area is depicted, featuring a large swimming pool surrounded by lounge chairs and shaded by umbrellas. A shallow hot tub is positioned in the foreground. People can be seen relaxing on the chairs and enjoying the water.

Home in Wintergreen Resort

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

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

4.94 out of 5 average rating, 226 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.

Top guest favorite

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.

Condo in Wintergreen Resort

4.99 out of 5 average rating, 158 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

Superhost

An in-ground pool is centered on a spacious deck, surrounded by lounge chairs. The house, with a grey roof, stands in the background against a backdrop of rolling hills and a cloudy sky, providing a serene outdoor space.

Home in Lovingston

4.85 out of 5 average rating, 297 reviews

Secluded Mountain Cabin w/ Pool, Trails & Winery ❤️

Nestled in Mountain Cove with views of Mountain Cove Winery, this property offers 100MB high-speed internet, adjacent to 800 acres of hiking trails. With an in-ground pool, deck, and firepit area, it's 35 minutes from Wintergreen, surrounded by wineries, breweries, and horseback riding. Ideal for creating memories. Note* Pool is not heated and closed when it’s cold. Ask before booking if the pool is open if you plan to swim.

Guest favorite

Home in Nelson County

4.9 out of 5 average rating, 49 reviews

Boho Mountain: Heated Pool, Hot Tub, Brews & Vines

Ideal for a large family, few couples, or girlfriends to spend a long weekend. In the Heart of Nelson County, find this 3 bedroom / 2 bath home with a hot tub, heated pool, and private yard on a quiet country road w/ incredible mountain views! Home is modern and clean with space for 8. Walk to Blue Mountain Brewery and take a 5 minute drive to Lovingston Winery... Crabtree Falls, Fruit orchards, and vineyards abound!

Top guest favorite

An open living area is highlighted by a large blue sectional sofa, a wooden coffee table, and a vibrant area rug. Natural light fills the space through expansive glass doors. A bar with four stools is visible in the background, leading to a well-equipped kitchen.

Townhouse in Roseland

4.98 out of 5 average rating, 103 reviews

Idyllic refuge for outdoors, ski, relaxation & WFH

Visiting Wintergreen? Whether for hiking, skiing, or enjoying distilleries in the valley below, this spacious and comfortable townhome has everything you need to maximize your holiday. Enjoy your morning coffee on the magnificent deck, watching the sun rise over the mountains, and end your day with a cozy fire. You're just steps away from the Inn, mountain restaurants and the lifts!