Wintergreen vacation rentals

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Popular amenities for Wintergreen vacation rentals

Other great vacation rentals in Wintergreen

Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 172 reviews

Best View in the Blue Ridge from Biscuit's Porch

Jun 23 – 30

R3,630 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 105 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

Mar 21 – 28

R2,942 ZAR per night
Guest favorite

Condo in Roseland

4.94 out of 5 average rating, 202 reviews

Mountain Getaway - Unbeatable Views

Jun 20 – 27

R2,557 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.89 out of 5 average rating, 126 reviews

Condo - King Master Suite - Wintergreen Resort

Jul 9 – 16

R2,476 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.91 out of 5 average rating, 100 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

Jul 12 – 19

R3,259 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 235 reviews

Five Minute Walk to Everything!

Dec 20 – 27

R3,931 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 120 reviews

Slope side+Panoramic Mountain Views!

May 24 – 31

R3,471 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.96 out of 5 average rating, 155 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

Aug 30 – Sep 6

R3,464 ZAR per night

Wintergreen house rentals

Guest favorite

Home in Shipman

4.88 out of 5 average rating, 117 reviews

The Refuge at Laurel

Nov 13 – 20

R2,160 ZAR per night
Guest favorite

Home in Wintergreen Resort

4.95 out of 5 average rating, 193 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Sep 28 – Oct 5

R3,634 ZAR per night
Guest favorite

Home in Roseland

4.9 out of 5 average rating, 127 reviews

Charming Farmhouse in a great location!

Apr 16 – 23

R3,623 ZAR per night
Guest favorite

Home in Faber

4.99 out of 5 average rating, 117 reviews

Buck Creek Lodge (2 bedrooms) Hidden in Blue Ridge

Jun 10 – 17

R3,285 ZAR per night
Guest favorite

Home in Nellysford

4.99 out of 5 average rating, 100 reviews

Glass House | Mountain & Water Views @ Wintergreen

Oct 16 – 23

R15,628 ZAR per night
Guest favorite

Home in Wintergreen Resort

4.97 out of 5 average rating, 152 reviews

Ski-In/Ski-Out Renovated Chalet on Lower Tyro

Jun 3 – 10

R5,836 ZAR per night
Guest favorite

Home in Stuarts Draft

4.85 out of 5 average rating, 263 reviews

Blackwood Air B & B

Aug 14 – 21

R2,107 ZAR per night
Guest favorite

Home in Greenwood

5.0 out of 5 average rating, 153 reviews

Gorgeous Modern Mountain Home + Blue Ridge Views

Feb 9 – 16

R10,303 ZAR per night

Ski-in/ski-out vacation rentals in Wintergreen

Guest favorite

Home in Wintergreen Resort

4.93 out of 5 average rating, 27 reviews

Top of the Lift Mountain Getaway

May 2 – 9

R2,019 ZAR per night
Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 13 reviews

Cozy Condo in Wintergreen Resort That Sleeps 4!

Aug 6 – 13

R2,130 ZAR per night
Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 30 reviews

Ski-in/out: Dogs OK+Fireplace+Pack ’n play+Parking

May 20 – 27

R2,000 ZAR per night
Guest favorite

Apartment in Wintergreen Resort

5.0 out of 5 average rating, 31 reviews

Mountain View Nest

Sep 1 – 8

R3,114 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 38 reviews

Cozy little condo, near slopes.

May 5 – 12

R2,131 ZAR per night
Guest favorite

Apartment in Wintergreen Resort

4.92 out of 5 average rating, 12 reviews

New! Cozy condo in the Mountain Inn!

Aug 14 – 21

R2,133 ZAR per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 42 reviews

Mountain condo! - Close to everything!

May 13 – 20

R2,173 ZAR per night
Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 70 reviews

1 bedroom condo close to hiking breweries & resort

Oct 30 – Nov 6

R2,919 ZAR per night

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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