
Wintergreen Resort vacation rentals
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Top-rated vacation rentals in Wintergreen Resort
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Ski-in/ski-out vacation rentals in Wintergreen Resort

Wintergreen condo ski-in/ski-out
Superb Airbnb! Felt right at home with everything they supplied for this unit. Extremely clean. View was great and walkable to the slopes and the market! Would highly recommend and looking forward to staying again for spring or summer!

Mtn/Firework Views from Private Deck ~ King Suite
My fiance, our dog, and I had a wonderful stay at Susie's! The condo was well stocked with anything you may need during your stay. The dog bowls and towels were a thoughtful addition right as you walked in. The bed was comfortable and we loved having the TV up there to unwind after a day of hiking around nearby trails. We ended up having to reschedule the days that we were coming, and Susie made that process very easy. We will definitely be staying here again next time we come to the area!

Brown Bear Lodge, walk to the slopes!
Brown Bear Lodge was a beautiful home! Jane was Ana amazing host, very responsive and helpful. The location was great, walkable to ski slopes and restaurants with an amazing view. Comfortably fit me and my girl friends.

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge
We had a great time. The yurt is in a very secluded and peaceful area, and the surrounding mountains are good for moderate to difficult hiking. There’s a small lake with a pedal boat and a couple swimming platforms. There’s also a hot tub a short walk from the yurt (though we didn’t use it). The yurt itself is large and spacious. It’s very sturdy. The deck is very large, too. Great for unobstructed night sky views. The inside is very clean, and although there is no TV hook up you can bring your own DVDs to watch. There are magazines and quite a few interesting coffee table books as well. So if you forget to bring a book, no worries. It’s a great place to get away from it all. I recommend highly and would rent again.

Fantastic home in an ideal location, dogs welcome!
Kathryn was a wonderful host and made our stay very comfortable. We had a great time and truly appreciated the thoughtful hospitality. She was kind enough to allow an early check-in, which was a big help for our schedule. The detailed guide provided was super handy and made settling in easy. Our kids had a wonderful time, especially with the toys available. When we noticed a missing battery in the remote, Kathryn responded immediately and resolved it right away. We did have a hiccup with the AC not working one evening, but she was incredibly apologetic, communicated openly, and even issued a partial refund without us asking. We really appreciated the honesty and care. The house was well-equipped with everything we could need, from toiletries and kitchen utensils to camping chairs and kids’ toys. The attention to detail made our stay comfortable and hassle-free. Overall, a very communicative and easy-to-work-with host. We’d happily stay again.

Ski-in/Ski-out Wintergreen Highlands Condo -Views!
Lindsay’s place was perfect for our family’s ski weekend. The condo was spacious and had everything we needed. The views were amazing! Lindsay was a great communicator and very responsive host. Highly recommend!

Ski-In/Ski-Out Renovated Chalet on Lower Tyro
Absolutely a 5 star stay!! Super cozy home in a beautiful location with a great view. The home is stocked with everything you could need to feel right at home (and labeled, making things very easy to find!). Everything inside was also extremely clean and tidy. My friends and I would definitely book again for another girls weekend away.

Family Friendly Home with All Necessities Included
This is a beautiful mountain home with big picture windows and a large porch tucked among oak trees and rocky outcrops. It is attractive and homely, with lots of comfortable furniture and fun decorations. The well-stocked kitchen and large dining area was perfect for our family of six. The king size master bedroom is up some reasonably steep stairs, but the bed is very comfortable! We were able to drive down to the Wintergarden Pool to park for the ski shuttle (and you can also reasonably walk from there to the top of the Highlands expert slopes), as well as do quick 10 minute drives down the mountain to drop and pick up our skiers. Thanks!
Other great vacation rentals in Wintergreen Resort

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~
We loved staying at Bluebird Mountain Home. The house is in pristine condition with a billiard room and comfy couches and chairs to kick back. The screened-in porch provided ample room for our board games and visits at night. The kitchen is huge with plenty of counter space and a pantry that is fully stocked with anything anyone could ever need. We enjoyed this house immensely and plan to return.

Hilltop Escape At Wintergreen
This place was really beautiful and worked perfectly for our group of 10 for a cabin weekend. The house is super spacious, with lots of privacy, especially on the top floor. The large windows looking out on mountain views made the place feel luxurious and super peaceful. Location is great for taking advantage of the area. The hot tub was a big hit, as was the indoor fireplace. The kitchen was really well stocked with pots, pans, dishes, silverware, etc. There were plenty of towels, linens, and blankets. Hosts Zee and Sarah were extremely communicative in the weeks/days leading up to our stay, always responding quickly. They were professional and helpful and we felt very well taken care of. There were a few items/spaces in the house that could use some updates/TLC, which we made hosts aware of and they were very responsive. It is also worth noting that there is no phone service up at the cabin until you get on wifi. Thank you Zee and Sarah! We would definitely stay here again.

Gorgeous Sunrises (The Cliffs)
We spent the weekend here to go snowboarding. It was very walkable to drop in at highlands or wait for the shuttle. Check in was easy and the kitchen was amazing. The view was incredible.

Modern 5BR Home | Spacious Getaway in the Valley
There is a ton of space in Arturo's place, two full baths and two halfs, and plenty of beds. Well decorated and well lit. Great TV/Multi-media. It was perfect for a large group. We would definitely rent again.

Blue Ridge Cabin 5
Spent New Year's with my husband and two Yorkies nestled deep in the woods, and it was everything I hoped for—and more! The property is surrounded by towering trees, offering a sense of tranquility and seclusion that's hard to come by. The bed deserves a special mention— it was the most comfortable bed I’ve ever slept in! We spent all three days hiking some of the best trails and relaxed comfortably watching TV in the evenings with a nice glass of Malbec. If you're looking for a peaceful retreat where you can reconnect with nature without sacrificing comfort, this Airbnb is the perfect choice. I’ll definitely be returning! Thank you Jerry and Chris.

Dog Friendly - Backs to Golf - Spacious Deck
Pip's place is close enough to all the features that Wintergreen Resort offers to make them easily accessible, but far enough away to give you space and quiet. It backs up to the golf course so the back has a lovely setting. We were especially grateful that the place is dog friendly. We would totally recommend this spot and would stay again in the future.

Mima’s Mountain House with Mountain view/Creekside
The house was really spacious, clean, and well stocked! Appreciated the hosts responsiveness. Will definitely rent this house again!!!

Cozy Creekside 2-bedroom home.
The place was very clean and perfect for us — 2 couples and a couple of small dogs. We came to town to enjoy some skiing at wintergreen and found the location convenient for access to the resort at a very fair price. It was a very cold weekend so we didn’t get much opportunity to enjoy the outdoor patio or fire pit but we enjoyed the view of the beautiful creek.
Quick stats about vacation rentals in Wintergreen Resort
Total rentals
670 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
25K reviews
Family-friendly rentals
520 properties are a good fit for families
Pet-friendly rentals
220 properties allow pets
Rentals with a pool
420 properties have a pool
Frequently Asked Questions
How much does it cost to stay in apartment rentals in Wintergreen Resort?
Experience the best of Wintergreen Resort with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Wintergreen Resort?
Yes! Work meets play with ease at over 240 vacation rentals in Wintergreen Resort featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Wintergreen Resort condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 240 condo rentals with pools in Wintergreen Resort, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Wintergreen Resort?
Four-legged friends are welcome in Wintergreen Resort. Choose from more than 220 vacation rentals for guests traveling with pets.
Do house rentals in Wintergreen Resort have self check-in?
Absolutely! We offer over 90 house rentals with self check-in in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wintergreen Resort have wireless internet?
Absolutely! We offer over 220 house rentals with wireless internet in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wintergreen Resort have a gym?
Absolutely! We offer over 40 house rentals with a gym in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Do chalet rentals in Wintergreen Resort have a bbq area?
Absolutely! We offer over 10 chalet rentals with a bbq area in Wintergreen Resort. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly townhouse rentals in Wintergreen Resort?
Wintergreen Resort has more than 20 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Wintergreen Resort?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with a bbq area, over 90 homes with self check-in, over 40 homes with a gym, over 220 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Family-friendly rentals Wintergreen Resort
- Rentals with a fireplace Wintergreen Resort
- Rentals with pools Wintergreen Resort
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- Ski-in/ski-out rentals Wintergreen Resort
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- Kid-friendly rentals Wintergreen Resort
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- House rentals Wintergreen Resort
- Rentals with a fire pit Wintergreen Resort
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- Apartment rentals Wintergreen Resort
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- Massanutten Resort
- Omni Homestead Resort
- Ash Lawn-Highland
- Chisholm Vineyards at Adventure Farm
- Homestead Ski Slopes
- Spring Creek Golf Club
- Early Mountain Winery
- Amazement Square
- Massanutten Ski Resort
- Frontier Culture Museum
- Wintergreen Resort
- Liberty Mountain Snowflex Centre
- Boonsboro Country Club
- The Plunge Snow Tubing Park