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Vacation rentals with a pool in Wintergreen Resort

Find and book unique homes with a pool on Airbnb

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Popular amenities for Wintergreen Resort rentals with a pool

House rentals with a pool

Guest favorite
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.
Home in Wintergreen Resort
4.96 out of 5 average rating, 27 reviews

Stunning Views, Hot Tub, Impeccable Design

MonikaRating, 5 stars1 day ago
We spent a great week at Susan’s place. The location and views were terrific. The house was extremely well stocked and the host was super responsive. Would highly recommend.
Guest favorite
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
5 out of 5 average rating, 16 reviews

Hot Tub! Wintergreen Resort!

AliciaRating, 5 stars2 weeks ago
Our time at Camille’s place was wonderful and over too soon! We loved the area for its beauty and peaceful serenity, and the home was stocked with anything we could need. Camille was a great host, and was very responsive while providing great instructions.
Top guest favorite
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.
Home in Wintergreen Resort
5 out of 5 average rating, 18 reviews

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views

DeanaRating, 5 stars2 weeks ago
We had a great time at this beautiful house. The views were spectacular and the house and amenities were perfect. We celebrated my husband’s 50th birthday here with friends and family and we all had a great time with plenty of space for everyone.
Guest favorite
A serene pool reflects the early evening sky, framed by distant mountains and lush greenery. A shaded pergola with seating is positioned nearby, creating a relaxing space for guests to enjoy the peaceful surroundings.
Home in Afton
4.94 out of 5 average rating, 144 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars1 week ago
We stayed here for a bachelorette weekend and had a great time. The house was even bigger and cozier than I anticipated and the views were gorgeous. We loved being on the same property as Cardinal Point Winery and walked down to do a tasting/enjoy some bottles. The kitchen was stocked with all the tools we could have needed and the pool area was great!
Superhost
A living room area features a queen sofa bed, accented with decorative cushions. A small green side table is positioned beside a cozy armchair. A colorful area rug lays on the floor, and wall art depicting a serene forest scene adds visual interest. Natural light enters from a nearby window.
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Casa Perfecta

JosephRating, 5 stars2 weeks ago
We had an amazing stay at this beautiful condo in the mountains! The location is perfect for anyone looking to hit the slopes or tour the grounds – making it great destination year round. The condo itself is cozy, clean, and has everything you need for a comfortable stay. The kitchen was well-equipped, which made it easy to cook meals before heading out for the day. The beds were super comfortable, and we slept like babies every night! The host was incredibly helpful, providing us with all the information we needed for the resort, and even sent us local recommendations for dining and things to do in the area. Check-in and check-out were a breeze. Would definitely recommend this place to anyone looking for a relaxing, convenient, and picturesque retreat. We’ll be back next year for sure!
Guest favorite
The farmhouse exterior is set among autumn foliage, framed by trees with colorful leaves. Large windows dominate the front, allowing natural light to fill the interior. A gravel driveway leads to the welcoming entrance, showcasing the welcoming style of the home.
Home in Wintergreen Resort
4.89 out of 5 average rating, 66 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

Adou,MRating, 5 stars1 month ago
I was looking for a quiet place in the middle of the nature for our 10 years of marriage anniversary and I think we found the best one. Charlotte was so kind and helpful, she helped me surprised my wife with such a beautiful decoration. We were so impressed. My kids were so happy 😊😊 to see something different. If you’re looking for something really peaceful, nice, looking at the beautiful nature in the mountains, you are definitely at the right place. Thank you Charlotte for making our stay so special.😊😊😊😊 It was a really good experience and we definitely have to go back….
Guest favorite
A cozy lounge area features a plush blue chaise with golden legs, positioned near large windows dressed in white curtains. Natural light fills the space, highlighting a view of the surrounding trees and mountains.
Home in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Amazing Views | Hot Tub | Mins to Breweries

SarahRating, 5 stars3 weeks ago
We very much enjoyed our stay, the view from the porch was amazing! Michael was very responsive. The house was well appointed and we loved that there was a Pack n’ Play available for our little one so we didn’t have to pack ours.
Superhost
An outdoor pool is set in a tranquil area, surrounded by lush greenery and colorful flowers. Poolside loungers and umbrellas are positioned along the edge, providing shaded seating. The clear blue water invites relaxation under the sun, while a gentle slope leads to the pool entrance.
Home in Schuyler
4.79 out of 5 average rating, 111 reviews

Peaceful Cottage

EvelynRating, 5 stars8 months ago
We stayed at Diana’s place while visiting with our daughter for our annual apple picking trip. Her place was a bit far out away from things, which we expected. It was cozy and had everything we needed for the weekend. I would highly recommend this cozy cottage when you want to get away!

Condo rentals with a pool

Guest favorite
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.
Condo in Wintergreen Resort
5 out of 5 average rating, 20 reviews

On the mountain, pet and child friendly

Mary KayRating, 5 stars3 weeks ago
Perfect cozy getaway with beautiful views. Great location within walking distance to golfing, Nature Center, pool, spa & food.
Top guest favorite
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.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 49 reviews

Wintergreen! Dog friendly, cozy and comfortable

ColleenRating, 5 stars1 month ago
We had a fantastic weekend at Kim’s place. It was the perfect size for me, my husband, our daughter, and small dog. We enjoyed the balcony and the fireplace. Kim was super responsive and suggested local attractions. It was wonderful to unplug and be in the woods for a few days. Highly recommend!!
Guest favorite
A spacious living area features large windows that provide expansive views of the surrounding landscape. Comfortable seating includes a sectional couch and a reclining chair, arranged around a wooden coffee table. A sleek stone fireplace and a mounted television add to the contemporary decor.
Condo in Wintergreen Resort
4.92 out of 5 average rating, 25 reviews

Wintergreen Mountain Views - Diamond in the Slopes

KateRating, 5 stars2 weeks ago
We loved our stay. It was exactly what we were looking for. The house is wonderful and very comfortable. Our kids loved the house, the area around it, and the hiking.
Top guest favorite
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.
Condo in Wintergreen Resort
5 out of 5 average rating, 31 reviews

Buena Vista Panoramic Retreat: Million Dollar View

NicoleRating, 5 stars4 weeks ago
Our stay was fantastic! Absolutely beautiful place and location - as stated by others the views are spectacular. Super clean, very well appointed and comfortable. We will absolutely be back and are looking forward to it. The hosts were wonderful to work with!
Guest favorite
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.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 20 reviews

Recently updated - view of the Blue Ridge Mtns

JenniferRating, 5 stars5 months ago
This condo was perfect for a long ski weekend for our family of 4. Located close to slopes, clean and with a spectacular view! Would definitely stay again!
Top guest favorite
A cozy living area features a gray sofa adorned with decorative pillows, positioned against a stone fireplace. Natural light filters through large windows, highlighting a small dining table set for two. A beautiful area rug complements the warm tones of the space.
Condo in Wintergreen Resort
5 out of 5 average rating, 15 reviews

Mountain House

MargalitRating, 5 stars3 months ago
Great one bedroom condo with cozy but spacious living room and bedroom. Best highlight is that it is about a 7 minute walk to the slopes and the small resort village for wintergreen. Perfect spot for a getaway.
Guest favorite
An open living space showcases a modern kitchen island with green cabinetry and white countertops. A cozy seating area includes a gray sofa, and a stone fireplace serves as a focal point. A wall-mounted television is positioned above the fireplace, enhancing the inviting ambiance.
Condo in Wintergreen Resort
5 out of 5 average rating, 6 reviews

Overlook 180 degree views w/Peloton!

GaryRating, 5 stars1 month ago
We enjoyed our stay at the air key Airbnb. It is very nice and comfortable place that is well stocked and has a great view of the mountains in Valley. We will definitely stay here again. My only complaint through no fault of Airkey was the maintenance on the outside of the building with the lift beeping every 30 seconds got to be a little annoying. But once again, it was a great place to stay. Highly recommended.
Guest favorite
A comfortable living area is presented, featuring a gray sectional sofa and an ottoman adorned with a decorative pattern. Natural light filters through multiple windows, illuminating the space. A small desk with two chairs is positioned nearby, with a fireplace adding to the cozy ambiance.
Condo in Wintergreen Resort
4.82 out of 5 average rating, 51 reviews

Happy hour on the 18th Hole

KevinRating, 5 stars3 months ago
The place was perfect, we had a group of 4 and it fit us all very comfortably, and it was so nice being very close to the mountain. This is an absolutely fantastic option for those looking to ski/snowboard at Wintergreen and I heavily recommend it.

Quick stats about vacation rentals with a pool in Wintergreen Resort

  • Total rentals

    420 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    14K reviews

  • Family-friendly rentals

    310 properties are a good fit for families

  • Pet-friendly rentals

    140 properties allow pets

  • Rentals with dedicated workspaces

    120 properties have a dedicated workspace

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