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

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

Farmhouse on Working Vineyard
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!

Perfect house
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.

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

Hot Tub EV Charger Mntn View Fireplace Grill Pool
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….

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

Misty Mountain Cabin w/spa
The cabin was great to stay at and had some pretty awesome views! Highly recommend the hiking trails. Overall, a really great place.

Peaceful Cottage
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

On the mountain, pet and child friendly
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!

Wintergreen! Dog friendly, cozy and comfortable
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!!

Wintergreen Mountain Views - Diamond in the Slopes
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.

Recently updated - view of the Blue Ridge Mtns
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!

Nature’s Haven 1 Bedroom Condo Wintergreen Resort
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!

Overlook 180 degree views w/Peloton!
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.

Happy hour on the 18th Hole
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.

The Perch in Wintergreen Laurelwood
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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