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Cabin vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort cabin rentals

Cabin rentals with a hot tub

Top guest favorite
The exterior of the mountain home showcases a mid-century modern design, with large windows surrounded by trees displaying autumn colors. A spacious deck features seating areas and a fire pit, inviting gatherings. Soft lighting highlights the outdoor space, enhancing the connection with nature.
Cabin in Wintergreen Resort
5 out of 5 average rating, 65 reviews

Hot Tub & Views | Mid Century Modern Wonder

LemarzalaRating, 5 stars1 week ago
I had one of the best stays here! Everything was so cozy, and the communication was excellent. The location is perfect everything is nearby. It’s the ideal getaway for families, and the playroom is such a fun bonus with plenty of activities to enjoy indoors. Thank you so much for hosting us
Top guest favorite
A spacious retreat is nestled among the trees, featuring a green metal roof and a large deck extending toward the water. Reflections of the cabin and surrounding autumn foliage can be seen on the calm pond, creating a serene outdoor setting.
Cabin in Montebello
5 out of 5 average rating, 57 reviews

Roudy’s Retreat: Secluded Mtn Cabin -Hot Tub -Pond

VictoriaRating, 5 stars1 month ago
What a gorgeous setting for a restful retreat. All of the necessary extra items such as snacks and handy items were in place for us and Jaclyn was a responsive host. The beds were nice and comfortable and we felt right at home. We will book again!
Superhost
The cabin's exterior is framed by snow-covered trees, showcasing a rustic facade constructed from reclaimed logs. A wooden walkway leads to the main entrance, highlighting large windows that invite natural light. The roofline is gently sloped, and a stone chimney adds character.
Cabin in Wintergreen Resort
4.75 out of 5 average rating, 8 reviews

Historic Cabin Hot Tub Mntn View Dogs OK King Bed

ChadRating, 5 stars1 month ago
We loved this cabin! The decor was cute and rustic! The kids referred to it as the “Cracker Barrel Cabin!”The view from the back deck was beautiful and we thoroughly enjoyed evenings in the hot tub after hiking. The wintergreen location is perfect. Just a short drive away from breweries, hiking and good restaurants! We would definitely stay here again!!
Guest favorite
Cabin in Wintergreen Resort
4.93 out of 5 average rating, 76 reviews

Modern Cabin with Hot tub and Sauna

JillRating, 5 stars1 week ago
This was a great home for our large family to gather as a central location. Thank you for creating such an amazing space, we so appreciated the big table for meals!
Guest favorite
The cabin is nestled among lush green trees, showcasing a multi-level structure with wooden balconies and a roof. A warm sunset casts a colorful glow over the exterior, highlighting its welcoming design and natural surroundings.
Cabin in Wintergreen Resort
4.98 out of 5 average rating, 87 reviews

Amazing Views! Hiking, Gazebo, Hot Tub, Grill

AlmaRating, 5 stars3 weeks ago
This place was as described. We loved the layout of the house and the decor. Everything in the house is labeled (so you don’t have to guess which light switch to use), wonderful view, and private. The host is very responsive and proactive! The directions to the property were clear and all instructions were laid out in advance. Thank you for a great stay - we will definitely be back.
Top guest favorite
A wide view of rolling hills is captured at sunset, with vibrant colors dispersing across the sky. In the foreground, a solitary tree stands on lush green grass, with a winding path leading through the landscape.
Cabin in Lovingston
5 out of 5 average rating, 9 reviews

Blue Ridge Cabin

JimRating, 5 stars1 month ago
Exceeded our expectations! This is a beautiful, comfortable, relaxing and fun place to be. Clean, fully equipped, inviting, and the location is literally a breath of fresh air. The pool and hot tub were highlights for our entire family. The bathrooms and kitchen were pristine. The bedrooms were comfortable and everything was simple to use. All of the little details (linens, artwork, soaps, welcome note, etc.) made the experience feel personal. Thank You.
Top guest favorite
Cabin in Tyro
4.9 out of 5 average rating, 78 reviews

Cabin By The Falls

MeaghanRating, 5 stars1 month ago
This place is absolutely gorgeous! My friends and I loved the hot tub and pool while listening to the sounds of the creek running close by. Such a cool fun place.
Guest favorite
A cabin exterior is surrounded by lush greenery and flowering plants. The inviting entrance is highlighted by a light green door, with warm light visible through the windows, signaling a welcoming atmosphere. A gravel path leads up to the front steps.
Cabin in Lyndhurst
4.88 out of 5 average rating, 26 reviews

Three Ridges Cabin-kitchen, fireplace, jetted tub

BrysonRating, 5 stars4 months ago
had a blast wintergreen was 20 minutes away and super fun nice jetted tube and very peaceful place host was very quick to respond and very helpful told us good information aswell perfect place to visit and get away

Cabin rentals with a pool

Guest favorite
A two-story cabin is surrounded by lush trees, showcasing a wrap-around deck with multiple access points. Large windows are visible, allowing natural light to illuminate the interior. The well-maintained outdoor area features a carpet of fallen leaves and rocky elements scattered throughout.
Cabin in Wintergreen Resort
5 out of 5 average rating, 32 reviews

Huge Family Retreat in the Shenandoah

JoeRating, 5 stars4 months ago
Large home, perfect floor plan for our group of 4 adults and two children. The home was only a 2-mile Drive to the Wintergreen Resort. We were able to spend all day skiing and then heading home was a short 5-minute drive to a relaxing evening at the house. The dining choices were limited, we ate most meals at the resort which had three or four different restaurants. The home is well kept and had all the amenities we needed.
Superhost
The cabin features a wooden exterior complemented by multiple decks. Large windows provide ample natural light, showcasing views of the surrounding trees. A gradual pathway leads to the entrance, while the area is adorned with fallen leaves typical of a forested setting.
Cabin in Wintergreen Resort
4.91 out of 5 average rating, 75 reviews

4 BR cabin mins to trails & breweries pets welcome

TaraRating, 5 stars3 months ago
Beautiful house that is even larger and specious in person than on the photos. We had two separate families with 6 kids between us with tons of room. The kitchen is fully stocked with every utensil you could need. The TV had access to Netflix, Peacock, Hulu and Disney, which was a special treat for the kids. The house is only a 5 minute drive from the Mountain Inn at Wintergreen. The house has huge windows with beautiful sunrises and a view of the slopes. The driveway has lots of parking, but it is very steep. It snowed just before we arrived and it requires 4 wheel drive just FYI for anyone traveling! Overall it was an amazing stay and we can’t wait until we can come again.
Superhost
Cabin in Wintergreen Resort
4.85 out of 5 average rating, 93 reviews

'Slippery Slope' Cozy Cabin in Wintergreen Resort

PaisleyRating, 5 stars1 week ago
Comfortable stay, great location, awesome host! Wont stay anywhere else for our trips to wintergreen!
Top guest favorite
The cabin features a warm wooden exterior with a red metal roof, set against a backdrop of lush greenery. A spacious front porch is presented, supported by wooden columns and adorned by wooden railing, inviting guests to enjoy the surrounding nature.
Cabin in Wintergreen Resort
4.88 out of 5 average rating, 128 reviews

The Bear Dance Cabin at Wintergreen Resort

JesseRating, 5 stars3 months ago
I’d argue that this is one of the best places to stay in Wintergreen. The cabin itself is perfect. We are a young family and it was comfortable, clean, and had everything we needed. The location is also perfect. It is very close to all the attractions on the resort. Clay was a great host as well. The perfect amount of communication; engaged without being intrusive. I would recommend this place to anyone who wants to be sure their trip is easy and successful!
Top guest favorite
A gray cabin exterior is framed by lush greenery and a welcoming porch. A simple wreath adorns the door, and lanterns are placed beside the entryway, enhancing the inviting appearance of the home.
Cabin in Nellysford
4.96 out of 5 average rating, 51 reviews

Airy farm cabin beneath the mountains

DavidRating, 5 stars2 months ago
Overall, this place was great. We have a little one, so the playground, horse farm, pond, and large front lawn were perfect for keeping her entertained while we weren't exploring the surrounding areas. My only critic is that the pictures of the views were a bit misleading. You do not have a view of the mountains from your patio, but instead the view of a circular drive and the accompanying home where many folks park to go play tennis or pickle ball. You are also within about 50-100ft of 3-4 homes on the property. Despite this misrepresentation of the property, I would still recommend it as you have access to these amenities, are in beautiful area, and within close proximity to many small towns/breweries & wineries/Charlottesville/and hiking and other outdoor activities.
Top guest favorite
An inviting screened-in porch features a modern gas fire pit surrounded by a sleek glass enclosure. Two comfortable chairs with decorative cushions are positioned nearby, offering a peaceful view of the lush greenery outside through large glass windows.
Cabin in Wintergreen Resort
5 out of 5 average rating, 40 reviews

Your Favorite Getaway. EV charger- Walk to trails

BenjaminRating, 5 stars2 weeks ago
Absolutely loved this stay! Sarah and Doug were excellent hosts. They reached out, but did not intrude. Everything was just as it should be. Some little touches we especially loved: baskets of comfy blankets in each sitting room, toiletries well above hotel standard, EV charger, king bed. The location was very convenient to everything we wanted to do in the mountains. We can't wait to come back!
Guest favorite
An open-concept living space features a blend of rustic wooden beams and modern finishes. A comfortable leather sofa and armchair are positioned in the foreground, while the kitchen, dining area, and stairway leading to a loft can be seen in the background.
Cabin in Wintergreen Resort
4.92 out of 5 average rating, 39 reviews

Serenity Cabin: Woodland Retreat

DonRating, 5 stars1 week ago
We used to spend a decent amount of time at Wintergreen but hadn’t in several years. This beautiful home was a wonderful welcome back. The location is quiet and surrounded by beautiful ferns and woods. The home is comfortably furnished and well equipped. There’s a large deck to help you enjoy the surroundings. The location is right off the Blue Ridge Parkway and the resort itself has several hiking trails. We had originally planned to stay elsewhere but that fell through. Andrew and Allison responded quickly and allowed us to book at the last minute. We are very glad it worked out the way it did!
Top guest favorite
A spacious living area is highlighted by large windows that frame views of the surrounding greenery. A comfortable sectional couch faces a stone fireplace, complemented by a glass table. Natural light fills the room, enhancing the inviting atmosphere.
Cabin in Nellysford
4.93 out of 5 average rating, 83 reviews

Majestic Mtn Cabin + quick hike & overlook access

ChristiRating, 5 stars2 weeks ago
Brads place was wonderful. Everything you could need was there. The house was quite and comfortable. We would definitely stay there again. Would recommend brads place to anyone.

Pet-friendly cabin rentals

Guest favorite
The rustic cabin, crafted from logs, is nestled amid lush greenery. A stone chimney rises prominently, and a small porch extends around the front, providing an inviting entryway. The gravel path leads up to the house, surrounded by tall trees and open grass areas.
Cabin in Montebello
4.94 out of 5 average rating, 31 reviews

Country Roads Take Me Home.

Katie SandersRating, 5 stars1 month ago
The cabin was adorable and very close to some great hiking trails. It was very convenient having the general store so close. I really appreciate being able to bring my dog! I hope to stay at The Chimneys again. Thanks for everything!
Top guest favorite
A welcoming log cabin exterior features a spacious front porch with two comfortable chairs and a small table. The porch is framed by sturdy wooden beams, and neatly stacked firewood is visible on the side. Lush green grass surrounds the cabin, enhancing the natural setting.
Cabin in Schuyler
4.99 out of 5 average rating, 124 reviews

Very Private Cabin - H'Owl at the Moon Farm

MarkRating, 5 stars2 weeks ago
Words cannot describe the feeling of pure calm that comes over you when you arrive. This place is truly a treasure hidden in the woods. Once you cross the creek you leave the world and all your cares behind. The host pays attention to all the little details and it shows. We have stayed at quite a few places but this one is on our return list. We look forward to sliding up for a long weekend in the late fall or early winter. (Tip- be sure to spend 15 min reading the welcome package it is time well spent).
Guest favorite
A charming log cabin is showcased with a wrap-around deck, surrounded by trees and mountain views. The elevated structure features a sloped roof and a gravel driveway leading up to it, offering a peaceful retreat in a natural setting.
Cabin in Afton
4.97 out of 5 average rating, 86 reviews

Log Cabin w/ Views! 8+ Acres! Pets!

KarenRating, 5 stars1 day ago
Beautiful cabin and location. We had a very relaxing stay for our annual sisters’ weekend. Lots of wildlife. Thank you Michael and Karen for hosting us!
Top guest favorite
The A-frame cabin showcases large windows that enhance natural light and provide views of the surrounding wooded lot. A spacious front deck with seating opportunities is visible, inviting relaxation amidst the lush greenery.
Cabin in Wintergreen Resort
4.97 out of 5 average rating, 78 reviews

On The Rocks

WilliamRating, 5 stars2 weeks ago
The wood stove is a lot of fun, and the porch is so tranquil in the evenings. A wonderful summertime retreat to explore the valley and enjoy nature!
Top guest favorite
The cabin features a warm wooden exterior, nestled amid trees and natural foliage. A spacious front porch is visible, leading to a charming entrance. The well-maintained gravel driveway winds around the cabin, surrounded by a lush green lawn and fallen leaves.
Cabin in Faber
4.97 out of 5 average rating, 135 reviews

Summer Kayaking free Rockfish! 140 Acres,peaceful!

ShanaRating, 5 stars4 days ago
We stayed here for a wedding in Charlottesville and, while the cabin was a bit out of the way from where most guests were staying in town, it ended up being the best decision we made. Our group was too large for hotel rooms, and this cabin gave us the perfect place to spread out and relax. We honestly wished we had more time to enjoy the space itself—it's ideal for a peaceful getaway weekend. Unfortunately, wedding events kept us running around, but we could easily see ourselves coming back just to unwind and take it all in. The property offers plenty to do, and the atmosphere is cozy and inviting. A couple of small suggestions that would’ve helped us (specifically as guests getting ready for a wedding): a full-length mirror in the downstairs bathroom and some brighter lighting in the bathrooms for hair and makeup. That said, these things wouldn’t be an issue for a regular weekend trip. Overall, a charming cabin that we hope to return to when we can truly enjoy it!
Guest favorite
A modern cabin presents a black exterior with white trim and a sloped roof. Large windows allow natural light to enter the interior, while a welcoming deck features a railing for safety. Surrounding trees add a touch of nature to the setting.
Cabin in Montebello
4.91 out of 5 average rating, 32 reviews

Blue Ridge Parkway Cabin 7

SusanRating, 5 stars3 months ago
What a beautiful view of the Tye River from our porch! We wanted to experience a mountain snow weekend and that’s exactly what we got. Jerry was also able to accommodate an early check in so we were not driving in inclement weather.
Superhost
A charming log cabin is nestled among mature trees, featuring a semi-wraparound deck. The structure's natural wood finish blends with the surrounding greenery. Multiple entry points are visible, providing access to the inviting outdoor space.
Cabin in Buckingham
4.89 out of 5 average rating, 197 reviews

Lotus View Retreat in Yogaville / Cabin

Samantha Rating, 5 stars2 months ago
We loved the large deck with incredible views! There is another property very close to this one so wasn’t as secluded as we had hoped but overall we loved our stay here. Go check out Eagle Zen Winery if you have the chance.
Superhost
The cabin features a sloped roof and wooden exterior, nestled among trees. A wooden ramp leads to the entrance, enhancing accessibility. Surrounding the cabin, fallen leaves blanket the ground, indicative of the natural landscape. Clear skies provide ample daylight, illuminating the structure.
Cabin in Roseland
4.59 out of 5 average rating, 223 reviews

Cabin at Wintergreen! 3Bed/2Bath

JeanRating, 5 stars1 month ago
This is a great little cabin nestled in beautiful surroundings. There is a nearby overlook with awesome scenery perfect for family photos. Nice area to take walks and get the family into nature. Joseph, our host, was very attentive to any questions we had. Thank you, Joseph!

Quick stats about cabin rentals in Wintergreen Resort

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$25,098 GYD before taxes and fees

  • Total number of reviews

    2.4K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore