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Vacation rentals in Wintergreen

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Popular amenities for Wintergreen vacation rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Other great vacation rentals in Wintergreen

Top guest favorite
The living area highlights cathedral ceilings and a stone fireplace, flanked by large windows that provide expansive views of the outdoors. A comfortable seating arrangement features a sectional sofa and armchairs, complemented by a smart TV and built-in shelving.
Cabin in Wintergreen Resort
5 out of 5 average rating, 68 reviews

Hot Tub & Views | Mid Century Modern Wonder

MichaelRating, 5 stars1 week ago
A group of us used Joey’s home for a work retreat. It was a relaxing location that offered great space to focus and unplug.
Guest favorite
The treehouse is illuminated at night, showcasing its modern architectural features. Light spills from the large windows onto the surrounding woods, creating a contrasting glow. The outdoor deck is visible, framed by trees, with a pathway leading up to the entrance.
Treehouse in Roseland
4.92 out of 5 average rating, 63 reviews

Blue Ridge Treehouse

JacobRating, 5 stars1 month ago
Beautiful home with beautiful surroundings. Extremely peaceful and relaxing. Cant wait to come back!
Superhost
A picnic table is positioned on a grassy area, offering expansive views of rolling mountains under a partly cloudy sky. Lush greenery surrounds the table, creating a serene outdoor setting for relaxation or enjoying a meal.
Home in Wintergreen Resort
5 out of 5 average rating, 5 reviews

Casa Perfecta

AdamRating, 5 stars3 days ago
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
Cabin in Wintergreen Resort
4.98 out of 5 average rating, 90 reviews

Amazing Views! Hiking, Hot Tub, Pool Table, Grill

PeteRating, 5 stars5 days ago
The house was perfect for our group of three families; it was beautifully laid out and we enjoyed the spaces throughout. The game room was fun for both the kids and adults, and the kitchen is well stocked which was really important for our group. Mike was a pleasure to interact with and very helpful. We only stayed for two nights but all wished we had one more night!
Guest favorite
A dining area features a wooden table complemented by a bench, surrounded by glass walls that provide abundant natural light and views of the outdoors. A contemporary chandelier hangs above, and a textured blue rug anchors the space.
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 favorite
A wooden deck is furnished with three dark Adirondack chairs, positioned to offer views of the surrounding trees. The natural light filters through the leaves, creating a peaceful and inviting outdoor space for relaxation.
Cabin in Wintergreen Resort
5 out of 5 average rating, 42 reviews

Your Favorite Getaway. EV charger- Walk to trails

CassieRating, 5 stars1 week ago
Doug and Sara’s place was exactly the way that it looks online and exactly the way that it is written up online. It is clean, there’s plenty of linens, there special touches with small little things like coffee, ziplocks for leftovers, aluminum foil for our breakfast. The fridge is clean. Everything is nice. I would stay there again and I really hope we can come back again thank you very much. The best thing about this house is it super close to the Nelson 151 where all the brews and wineries are which is what we came up for and we came up for hiking all of that is very very close to their house. Additionally, the house looks like something out of a magazine. For two days we couldn’t find the microwave or the television so we didn’t use it but so we use the stove and then I looked in the drawers and everything is just beautifully put away.
Guest favorite
The loft bunk room features four twin beds built into the walls, each adorned with plaid bedding. A large window allows natural light to fill the space, while wooden beams and paneling create a cozy, rustic atmosphere. A dresser offers storage options in the room.
Cabin in Wintergreen Resort
4.93 out of 5 average rating, 40 reviews

Serenity Cabin: Woodland Retreat

MeganRating, 5 stars2 weeks ago
We had a great stay! My husband and I decided to take a last minute trip to the mountains with our boys on our way back from visiting family and found Andrew’s place. It was perfect for us! The house was well stocked, matched the pictures perfectly, and was very comfortable. We can’t wait to visit again!
Top guest favorite
A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.
Villa in Wintergreen Resort
4.97 out of 5 average rating, 89 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

SarahRating, 5 stars3 days ago
Ben’s place was lovely for our group! The living room is gorgeous, kitchen is well stocked, there is lots of bathrooms, and all the bedrooms were very cozy. The hot tub was also large and on a lovely patio. We enjoyed the fire pit and quiet surroundings on the deck as well.
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Your guide to Wintergreen

Welcome to Wintergreen

Sitting on the eastern slopes of the Blue Ridge Mountains — which are part of the Appalachian Mountains — is the Virginia destination of Wintergreen. Located about 40 minutes southeast of Charlottesville, the area is known for its wide-ranging elevations, from the deep valley floors to the majestic mountaintops. The community was built as a golf destination in the spring and summer and as a winter sports hub in the snowy months, making it the perfect mountain escape any time of year.

The best time to stay in a vacation rental in Wintergreen

The weather in Wintergreen doesn’t just depend on the time of year. It also hangs on elevation. The valley sits about 700 feet above sea level, giving it approximately the same climate as Charlottesville, adorned with a little mountain breeze, while the top of the mountain is a whopping 3,850 feet, meaning that the temperatures are typically 12 to 15 degrees Fahrenheit lower than in the valley. Daytime highs to evening lows can also swing about 20 degrees Fahrenheit. While the snow-covered slopes in the winter attract skiers and snowboarders to the area’s vacation house rentals — especially from December through March — summer has its own draws, with events such as the Wintergreen Music Festival and Academy and Old Wintergreen Day, celebrating the community. Craft shows also take place during Memorial Day Weekend, Fourth of July, Labor Day, and Oktoberfest.

Top things to do in Wintergreen

Outdoor Sports

From the beginning, Wintergreen was conceived as a year-round destination, with its golf resort opening in 1988 and its ski facilities opening a year later. Nowadays, those teeing off have a choice of two courses at Devils Knob and Stoney Creek, while skiers and snowboarders can choose from 24 trails, including 14 that are lit for night skiing. There’s also a 900-foot snow tubing hill and an ice skating rink that can hold 60 skaters. Other activities include tennis, boating, biking, hiking, ziplining, and flying high on the floating trampoline.

Rockfish Valley Trails

Five trails run through the south fork of Rockfish River and Reid’s Creek with six miles of pathways that are popular with hikers and birdwatchers. There are parking lots at the Rockfish River trailhead, as well as the 35-acre Spruce Creek Park, the only public park in Nelson County.

Skyline Drive at Shenandoah National Park

From Wintergreen, it’s about a 20-minute drive to the northern entrance of the Blue Ridge Parkway, Rockfish Gap Entrance Station. This is also the southernmost entrance point to the national park’s historic Skyline Drive, where the 105-mile stretch has its final mile marker near Waynesboro. From there, the scenic road stretches north along the crest of the Blue Ridge Mountains up to the mile marker 0 in Front Royal.

Destinations to explore

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