
Vacation rentals with a pool in Wintergreen Resort
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wintergreen Resort
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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.

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

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 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.

Cozy, clean, quiet mountain condo- King bed
Everything you need to make your getaway relaxing and convenient has been thought out in this tastefully decorated condo including new King Bed, Queen sofa pullout bed, plush linens, new spacious couch, 55" Smart TV, Roku, 1 Gbps internet, WiFi, DVD player & movies, fully equipped kitchen, dining area for 4, wood burning fireplace, and private patio. Non-smoking condo. Please provide all guest names and dog info if applicable upon inquiry or booking. No cats or other animals accepted.

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.

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.

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!

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

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

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.
Popular amenities for Wintergreen Resort rentals with a pool
House rentals with a pool

Cozy 5-bedroom home for large gatherings.

Pine Lake Lodge

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

All-Year Heated Covered Private Pool / Hot Tub

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

Bear's Mountain Escape

Misty Mountain Cabin w/spa

5 min toSki! Mntn View HotTub Pool Table MovieRoom
Condo rentals with a pool

On the mountain, pet and child friendly

Wintergreen! Dog friendly, cozy and comfortable

Recently updated - views of the Blue Ridge Mtns

Time To Get Away-Cozy Condo for 2 to 4

BeautifulFallFoliage/Ski-In/Out/PupsWelcome!

Overlook 180 degree views w/Peloton!

Love of mountains oh fill my cup

Happy hour on the 18th Hole
Other vacation rentals with a pool

Stunning Views, Hot Tub, Impeccable Design

Hot Tub! Wintergreen Resort!

Fantastic Mountain & Valley Views! Close to Resort

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

Luxury House on Mountain Golf Course near Slopes

4 min to Ski! Mntn View Hot Tub EV Charger Grill

Privacy and Views in Wintergreen

Cozy 3BR/2BR+Fire table+Foosball
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ760 | ﺩ.ﺇ735 | ﺩ.ﺇ617 | ﺩ.ﺇ606 | ﺩ.ﺇ628 | ﺩ.ﺇ613 | ﺩ.ﺇ599 | ﺩ.ﺇ595 | ﺩ.ﺇ595 | ﺩ.ﺇ617 | ﺩ.ﺇ610 | ﺩ.ﺇ676 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about vacation rentals with a pool in Wintergreen Resort

Total vacation rentals
Explore 450 vacation rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees

Verified guest reviews
Over 14,860 verified reviews to help you choose

Family-friendly vacation rentals
340 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 160 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
440 of Wintergreen Resort vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
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- Massanutten Ski Resort
- Frontier Culture Museum
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- The Plunge Snow Tubing Park
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