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Holiday 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

Top guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 20 reviews

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

JameelRating, 5 stars1 week ago
We enjoyed the house. It was a great place for eleven people and two dogs - spacious and comfortable. Kids (and adults) enjoyed the game room and large tv downstairs. The host was very friendly and communicated and responded to our questions very quickly. Peaceful location.
Guest favourite
Home in Afton
4.94 out of 5 average rating, 145 reviews

Farmhouse on Working Vineyard

SarahRating, 5 stars3 weeks 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
Home in Wintergreen Resort
5 out of 5 average rating, 5 reviews

Perfect house

AdamRating, 5 starstoday
I really enjoyed our stay. The wintergreen resort area was beautiful. Great views of the mountains! The home was in a very private area on a very quiet street with very quiet neighbors. Quiet all the way around! It was a short drive to the Devils knob brewery which was a great dinner, and the little market down the street had anything you needed in a pinch.
Guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 29 reviews

Luxury|Outdoor Lounge|Hot Tub|Fire Pit|Family&Pets

LauraRating, 5 stars1 week ago
Chris and his manager runs an excellent property. The property provides many thoughtful items to make your stay comfortable, enjoyable and homey. Only negative is HOAs rule that limits renters access to resort amenities.
Guest favourite
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….
Top guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 26 reviews

Luxury 5Bd 4Ba Sleeps 16+*Hot-tub*Dog Friendly*

MichaelRating, 5 stars1 month ago
My family and I had such a wonderful fantastic time staying at Michaels home.... He was quick to help out with any questions..the home fitted the 15 of us easily and everything from the time I opened up the front door till the time we left for home was execptional... Lots of stuff to do--Jenga tournaments/Pool/ Hot Tub.... We booked with Michael at the last minute for a sons college graduation and highly recomend this home and host... Thank you for making my sons weekend a great memory!!!! Mike H
Guest favourite
Home in Wintergreen Resort
4.82 out of 5 average rating, 160 reviews

Misty Mountain Cabin w/spa

BenRating, 5 stars1 month ago
The cabin was great to stay at and had some pretty awesome views! Highly recommend the hiking trails. Overall, a really great place.
Superhost
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!

Apartment rentals with a pool

Guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 22 reviews

On the mountain, pet and child friendly

ErikaRating, 5 stars1 week ago
We had a fantastic stay! Would love to book again. The space has a great lay-out, comfortable rooms, and the deck has a great private view overlooking the golf course. It’s a great location by overlooks, trails, and restaurants. The hosts were amazing and friendly, and very responsive . Thanks again for a great trip!
Top guest favourite
Apartment 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 favourite
Apartment in Wintergreen Resort
4.92 out of 5 average rating, 25 reviews

Wintergreen Mountain Views - Diamond in the Slopes

KateRating, 5 stars4 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.
Guest favourite
Apartment 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!
Guest favourite
Apartment in Roseland
4.9 out of 5 average rating, 63 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

PeytonRating, 5 stars3 weeks ago
My wife and I really enjoyed a weekend getaway at Mikki’s place. The condo has a great location with beautiful views and access to nearby Wintergreen amenities, and we took advantage of the less than 20 minute drive to multiple of the Nelson 151 breweries. Mikki is very responsive and we appreciated her recommendations and help in getting us get access to a nearby pool. Would stay again!
Guest favourite
Apartment 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 favourite
Apartment 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.
Top guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 39 reviews

The Perch in Wintergreen Laurelwood

BoscoRating, 5 stars3 months ago
We had a wonderful stay at Ashley’s place! The location was perfect for skiing. Ashley was very responsive - we would definitely stay here again!

Quick stats about holiday rentals with a pool in Wintergreen Resort

  • Total rentals

    420 properties

  • Nightly prices starting at

    ₹6,058 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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