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

Mountain Cottage, Ski Wintergreen, Nelson 151
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

Bear's Mountain Escape
Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

Cozy Lux Condo at Wintergreen Resort
The perfect little getaway nestled into the hillside and centrally located within Wintergreen Resort. Our place serves as a launch pad to explore the numerous, year round activities and attractions in the area or a quiet retreat designed for wine, movies, and a fire. With a full kitchen, large flat screen tvs, WiFi, fireplace, washer/dryer, and other everyday comforts you will feel right at home. A queen size blow up mattress is available for extra sleeping options in addition to the couch.

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, 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 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.

2-min drive to 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 CLOSED for season

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.

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

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.

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.

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!

Mountain View Condo at Wintergreen, Fireplace
Breathe in the crisp mountain air, cozy up by the fireplace, and soak in sweeping views of the Blue Ridge Mountains. This clean, comfortable 2-bedroom condo at Wintergreen Resort features two king beds, two full bathrooms, and a sleeper sofa—perfect for up to 6 guests. Enjoy panoramic windows overlooking the mountains,, a fully stocked kitchen, in-unit washer/dryer, central heat/AC, and free parking. The shuttle to the ski lodge is just steps away!

Cozy Condo - Sleeps 4
A wonderful weekend escape no matter the time of year. Condo has been completely renovated in the heart of Wintergreen Resort. Fully equipped condo for guests to come and enjoy the slopes. Within walking distance to the ski lift and all the amenities that the area has to offer. We are the only condo complex that also has a pool it's own pool for condo owners only. **the pool is for the condo complex and is shared with the other units.
Popular amenities for Nelson County rentals with a pool
House rentals with a pool

Cozy 5-bedroom home for large gatherings.

Cliffs Edge -A Contemporary Mountain Home

Pine Lake Lodge

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Seasonal Private Pool - All Year Hot Tub

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

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Misty Mountain Cabin w/spa
Apartment rentals with a pool

Wintergreen Ski Retreat, Cozy Condo Near Slopes

Wintergreen! Dog friendly, cozy and comfortable

Wintergreen Mountain Views - Diamond in the Slopes

Buena Vista Panoramic Retreat: Million Dollar View

Mountain View Vista: Resort Condo w/ Views

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

Cozy, clean, quiet mountain condo- King bed

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

Hot Tub! Wintergreen Resort!

Hot Tub + Game Room in Wintergreen for ski & fun

Weller’s Retreat at Stone Ridge

Huge Farmhouse, Heated Pool for Family Vacations

Perfect House

The Captain’s Quarters

Airy farm cabin beneath the mountains

Cozy 3BR/2BR+Fire table+Foosball
Destinations to explore
- Cabin rentals Nelson County
- Private suite rentals Nelson County
- Rentals with a hot tub Nelson County
- Rentals with a patio Nelson County
- Rentals with a firepit Nelson County
- Apartment rentals Nelson County
- Ski-in/ski-out rentals Nelson County
- House rentals Nelson County
- Pet-friendly rentals Nelson County
- Rentals with a fireplace Nelson County
- Chalet rentals Nelson County
- Farm stay rentals Nelson County
- Rentals with lake access Nelson County
- Rentals with outdoor seating Nelson County
- Rentals with a washing machine and dryer Nelson County
- Rentals with a kayak Nelson County
- Rentals with breakfast Nelson County
- Boutique hotels Nelson County
- Townhouse rentals Nelson County
- Bed and breakfasts Nelson County
- Flat rentals Nelson County
- Cottage rentals Nelson County
- Family-friendly rentals Nelson County
- Rentals with pools Virginia
- Rentals with pools United States
- Downtown Mall
- James Monroe's Highland
- Amazement Square
- Frontier Culture Museum
- Wintergreen Resort
- Blenheim Vineyards
- Liberty Mountain Snowflex Centre
- National D-Day Memorial
- Glass House Winery
- Cardinal Point Winery
- Devils Backbone Brewing Co Basecamp
- James Madison University
- University of Virginia
- Monticello
- John Paul Jones Arena
- White Lotus Eco Spa Retreat
- Virginia Horse Center
- James River State Park
- Appomattox Court House National Historical Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Massanutten Indoor WaterPark
- The Rotunda
- Family Adventure Park
- Natural Bridge State Park
- Things to do Nelson County
- Things to do Virginia
- Nature and outdoors Virginia
- Art and culture Virginia
- Sightseeing Virginia
- Tours Virginia
- Food and drink Virginia
- Things to do United States
- Sports activities United States
- Wellness United States
- Art and culture United States
- Sightseeing United States
- Entertainment United States
- Tours United States
- Food and drink United States
- Nature and outdoors United States




