Vacation rentals in Wintergreen
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Wintergreen
Guests agree: these stays are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wintergreen vacation rentals
Stay near Wintergreen's top sights
Other great vacation rentals in Wintergreen
Home in Wintergreen
4.84 out of 5 average rating, 125 reviewsGrand Chalet w/ Hot Tub - Near Wintergreen Resort
Home in Waynesboro
4.86 out of 5 average rating, 21 reviewsModern 5 Bedroom Home, 6 miles from Skyline Drive
Home in Wintergreen Resort
4.9 out of 5 average rating, 10 reviewsWintergreen Mountain House
Cabin in Montebello
5 out of 5 average rating, 21 reviewsBlue Ridge Cabin 5
Cabin in Wintergreen Resort
4.87 out of 5 average rating, 75 reviewsDog Friendly - Backs to Golf - Spacious Deck
Home in Crozet
4.96 out of 5 average rating, 48 reviewsGreat Winter Getaway
Home in Wintergreen Resort
4.9 out of 5 average rating, 80 reviewsBear Creek Lodge
Home in Lyndhurst
5 out of 5 average rating, 43 reviewsCozy Creekside 2-bedroom home.
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
- Richmond Vacation rentals
- Charlottesville Vacation rentals
- Cabins Vacation rentals
- Shenandoah Vacation rentals
- Lake Anna Vacation rentals
- Lynchburg Vacation rentals
- Blacksburg Vacation rentals
- Massanutten Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom