House vacation rentals in Wintergreen

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Popular amenities for Wintergreen house rentals

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 week 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, 18 reviews

Hot Tub! Wintergreen Resort!

MalenaRating, 5 stars1 week ago
Camille's place at Wintergreen was perfectly situated for our weekend at Devil's Backbone. The house was clean and tidy, it was easy to find, and her directions and instructions for getting there and getting in the house were spot on. it's an adorable little place and has plenty of room with the three bedrooms. We would love to come back and rent again. Our dog loved it too!!
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, 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 favorite
A charming farmhouse with a white exterior and green shutters is surrounded by lush gardens. A small round table with white chairs sits among blooming azaleas. Two large trees provide shade in the front yard, complementing the inviting porch.
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
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, 5 reviews

Casa Perfecta

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 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
An outdoor seating area is shown, featuring a circular fire pit surrounded by a low-profile seating arrangement. The mountain landscape beyond presents a gradient sky at sunset, with rich autumn colors and foliage enhancing the serene atmosphere.
Home in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Amazing Views | Hot Tub | Mins to Breweries

SarahRating, 5 stars1 month 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
A spacious open living area features large windows offering natural light and views of the outdoors. The area includes a comfortable sofa, dining space with chairs, and a modern kitchen equipped with a stylish island and fixtures, enhancing the room's contemporary rustic feel.
Home in Wintergreen Resort
4.79 out of 5 average rating, 104 reviews

Mntn View Hot Tub Pool Table Pool Tennis Golf

JeremyRating, 5 stars3 weeks ago
A wonderful property nestled in the Wintergreen Resort. While not part of the resort, the amenities and surrounding Breweries offered plenty to do while not relaxing in the hot tub or on the private deck. Beds were comfortable, and there was plenty of space for our family to spread out. Access to WiFi and movie channels were convenient and supplemented the secluded feel for a well balanced vacation. Highly recommend this rental for families and groups looking to get away for a relaxing and enjoyable time in the mountains. Bring your cameras and charge your phones to take pictures of the breathtaking views at and around the house!

Weekly house rentals

Guest favorite
A spacious mountain house is nestled among tall trees, surrounded by lush greenery. A gravel driveway leads to the entrance, showcasing the home's unique architectural features, including large windows that offer natural light.
Home in Wintergreen Resort
5 out of 5 average rating, 8 reviews

Greyhaven II

YvonneRating, 5 stars3 months ago
Hone was truly beautiful! Recently renovated in a great mid century model. We had a group of 11 and we were all at home instantly! Will definitely stay there again!!
Top guest favorite
A bright game room features a blue pool table at the forefront, surrounded by a variety of games like foosball and air hockey. Comfortable seating is arranged near large windows, allowing natural light to fill the space. Tall bar stools add extra seating options.
Home in Nellysford
5 out of 5 average rating, 74 reviews

Game Room & Hot Tub Near Wineries + Breweries

EmilyRating, 5 stars1 week ago
Incredible Airbnb across the board! Truly 5 stars! Hope to be back!
Guest favorite
A spacious outdoor living area features a modern hot tub with glowing blue water, surrounded by a custom-built bar. Soft lighting from overhead lanterns adds a cozy ambiance, while a large screen TV is mounted nearby, overlooking the tranquil wooded surroundings.
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 favorite
A hot tub is situated on a wooden deck surrounded by lush greenery, with sunlight filtering through the trees. The tub is filled with clear water, inviting relaxation in a serene outdoor setting.
Home in Wintergreen Resort
4.92 out of 5 average rating, 53 reviews

Whispering Creek Hot Tub Pool TennisGolf King Beds

SylviaRating, 5 stars3 weeks ago
We absolutely loved our Memorial Day weekend getaway. The house has everything you need, a well stocked kitchen, comfortable beds & a fantastic deck with a hot tub. The owners were very responsive and helpful and we are already talking about planning a return trip in the Fall.
Top guest favorite
An inviting outdoor space features a hot tub, a gas fire pit, and comfortable seating arrangements. The area is designed for relaxation, showcasing smooth wooden decking and views of the surrounding trees. Sliding glass doors provide access to the interior of the home.
Home in Wintergreen Resort
5 out of 5 average rating, 59 reviews

Luxe Modern Retreat: Steps to Ski & Hike! Views!

ChristineRating, 5 stars2 months ago
The house was awesome! Clean, comfortable, parking, beautifully decorated. Bed rooms, kitchen and bathrooms were amazing and stocked well. The views were amazing! Loved the covered seating area outside. Beautiful. Highly recommend the house!
Top guest favorite
The home is nestled among trees, showcasing a two-level structure with multiple decks. The warmth of wood accents is complemented by large windows that invite natural light. A peaceful, wooded landscape surrounds the property, offering a sense of privacy and tranquility.
Home in Wintergreen Resort
5 out of 5 average rating, 63 reviews

Heart of Wintergreen, Hot Tub, Fireplace

SeanRating, 5 stars4 weeks ago
Dru, from moment one was responsive and answered all my questions with joy. This house is truly just lovely and even bigger and more open concept than i thought it was going to be based on the photos. The master bedroom with a king size bed on the main floor was my favorite space (my room) i did not want to leave that shower and jacuzzi tub! It was truly enough space for all who came with me. I was their for my 30th birthday and we played 4 days of golf at Devils Knob and Stoney creek, and everyone had more than enough room there was 7 of us. The kitchen was also well stocked and appliances were easy to use. I loved the gas grill we had a day or 2 of hamburgers and hotdogs. Also, it is of course its close to devils backbone and some of the other breweries off of route 151, I've marked this house as a favorite of mine and will always look for availability here first :) thank you Dru for letting my ring in my 30's in your beautiful home!
Guest favorite
A spacious great room features a stone fireplace as its focal point, surrounded by large windows that offer views of the sunset and surrounding trees. Leather couches and a glass coffee table complement the modern decor, while a plush ottoman provides extra seating.
Home in Wintergreen Resort
4.95 out of 5 average rating, 55 reviews

Panorama Peak Lodge-4 bedroom with sweeping views

ThereseRating, 5 stars1 month ago
We thoroughly enjoyed Panorama Peak and would stay again. It’s true that the photos don’t do justice to the spectacular views. We even got to see the deer that circle the property regularly. The house interior is spacious and beautiful and you can tell that it is well maintained. Everything was as described. The kitchen was clean and had a good supply. The bathrooms were clean with plenty of towels. Lauren was very responsive to all of our inquiries. Overall, the experience was easy. Our stay was as for a law school graduation in May. I can only imagine how beautiful it is there with the snowfall and that amazing fireplace. Highly recommend Panorama Peak. Thank you!
Top guest favorite
A spacious living area is highlighted by tall windows allowing natural light to fill the space. The inviting seating arrangement surrounds a floor-to-ceiling stone fireplace, while a large wall-mounted TV provides entertainment options. An open layout connects the living room to the dining area.
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

Private house rentals

Top guest favorite
A modern kitchen features a large island with a granite countertop and seating for several guests. The cabinets are white with sleek hardware, and high-end appliances are visible. Large windows provide natural light and a view of the surrounding trees.
Home in Wintergreen Resort
5 out of 5 average rating, 17 reviews

Wintergreen condo ski-in/ski-out

DaranRating, 5 stars1 month ago
It was a beautiful place that felt like home. The owners were amazing and responded very quickly. We will definitely come back!
Top guest favorite
The modern cottage features a light-colored exterior with large windows and a red front door. A wooden deck extends from the entrance, surrounded by lush green grass and trees displaying autumn leaves in shades of orange and yellow.
Home in Afton
4.98 out of 5 average rating, 82 reviews

Mountain View Meadow Cottage

NickRating, 5 stars3 weeks ago
A great get away with a beautiful view so close to so many wineries and breweries!
Guest favorite
A recently renovated treehouse is positioned among bare trees along a winding driveway. The facade features a combination of dark wood and large windows. A vehicle is parked nearby, with a sign visible in the foreground, indicating the property's welcoming presence amidst a serene natural setting.
Home in Roseland
4.93 out of 5 average rating, 74 reviews

The Treehouse at Wintergreen

BrandonRating, 5 stars1 month ago
I enjoyed the stay and Beth was a great host! Everything was as described and she was extremely detailed in instructions to make the stay as easy as possible. I would recommend the stay for anyone wanting a mountain getaway or explore the Wintergreen area!
Top guest favorite
A spacious home is positioned atop a gently sloping, lush green knoll. Its architecture combines modern design with natural surroundings. The expansive front porch offers a welcoming entry, while the backdrop features a clear sky transitioning from daylight to dusk.
Home in Afton
5 out of 5 average rating, 33 reviews

The Vū, Afton w/ 360º Mountain Views

KristaRating, 5 stars1 month ago
We could not have asked for a better stay at the Vū. The home was as beautiful as the photos and the scenic background made it hard to leave. The house is near several vineyards and popular local spots but is set back from the road and neighbors, so felt very private. It’s clear that Emily put careful thought into every detail of the space, from the furniture to the amenities and fully-stocked kitchen. The screened porch was an exceptional feature. I stayed with my family and the space was more than enough to accommodate all of us. I absolutely recommend the Vū for your next mountain getaway!
Top guest favorite
The living area features a central coffee table made of natural wood, surrounded by a light gray sectional sofa and two brown leather chairs. A stone fireplace serves as a focal point, with a mounted television above. Skylights above provide ample natural light.
Home in Wintergreen Resort
5 out of 5 average rating, 13 reviews

Away from it ALL

MegRating, 5 stars4 months ago
Away from it ALL was just what we were looking for! Our family of 5, plus grandparents had plenty of space to relax. All of the amenities were as listed and very generous. The home is nestled in the woods and we spotted deer each evening. The kitchen supplies were so helpful. The home is about a 5 minute drive from Wintergreen resort. We would definitely stay here again!
Guest favorite
A cozy living area is presented with a large sectional sofa in rich brown tones, complemented by a light-toned accent chair. A flat-screen television is mounted above a modern stone fireplace. Natural light filters through blinds on the windows, enhancing the warm ambiance.
Home in Roseland
4.9 out of 5 average rating, 31 reviews

Mountain retreat with hot tub

NicoleRating, 5 stars1 month ago
Great location easy to find, very beautiful surroundings, never been to Wintergreen before came for just the weekend with girlfriends. Booked a spa package and very close to that location. Ate at the restaurant nearby, mediocre at best. Did a driving tour of the 151 breweries and wineries and had a great time!
Superhost
A wooden deck features several Adirondack chairs arranged around a fire pit, providing a cozy setting for relaxation. Expansive views of the surrounding mountains and valleys are visible beyond the railing, with a mix of trees and rolling hills extending into the distance.
Home in Wintergreen Resort
4.87 out of 5 average rating, 71 reviews

Luxury Lodge: Stunning All-Season Views! Sleeps 14

KatieRating, 5 stars3 weeks ago
This place was the perfect fit for a weekend getaway with the girls. The views from the deck were amazing and so peaceful. Wineries and breweries within a 15 minute drive. There was plenty of space for all of us to feel at home. I would highly recommend this place to anyone looking to stay in the area.
Top guest favorite
A spacious deck features two lounge chairs and two wooden rocking chairs, offering a setting for relaxation. The surrounding area showcases lush green mountains under a clear blue sky, with expansive views of the valley below.
Home in Afton
4.97 out of 5 average rating, 36 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

AlexRating, 5 stars2 weeks ago
The photos don’t do it justice - the views were immaculate, the location was excellent, and the home was a piece of serenity in Afton. Wendy was a wonderful host, very responsive, and kind. Would rent this again in a heartbeat.

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