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

4.96 out of 5 average rating, 105 reviews

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

Dec 12 – 19

G$32,211 GYD per night
Guest favorite

Condo in Roseland

4.94 out of 5 average rating, 202 reviews

Mountain Getaway - Unbeatable Views

Jun 25 – Jul 2

G$28,360 GYD per night
Guest favorite

Condo in Wintergreen Resort

5.0 out of 5 average rating, 105 reviews

Mountaintop Getaway - Dog Friendly

Jul 10 – 17

G$42,575 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.89 out of 5 average rating, 126 reviews

Condo - King Master Suite - Wintergreen Resort

Jun 28 – Jul 5

G$27,110 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.89 out of 5 average rating, 107 reviews

1720 High Ridge at Wintergreen Resort

Jun 18 – 25

G$25,353 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 120 reviews

Slope side+Panoramic Mountain Views!

May 21 – 28

G$38,345 GYD 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!

Sep 6 – 13

G$37,928 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.99 out of 5 average rating, 141 reviews

3 BR 3 BA, 2 story condo in Highlands

Jan 1 – 8

G$62,686 GYD per night

Wintergreen house rentals

Guest favorite

Home in Shipman

4.88 out of 5 average rating, 116 reviews

The Refuge at Laurel

Oct 21 – 28

G$23,647 GYD per night
Guest favorite

Home in Stuarts Draft

4.85 out of 5 average rating, 261 reviews

Blackwood Air B & B

Aug 22 – 29

G$22,217 GYD per night
Guest favorite

Home in Wintergreen Resort

4.97 out of 5 average rating, 151 reviews

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

Dec 5 – 12

G$64,090 GYD 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 3 – 10

G$35,969 GYD per night
Guest favorite

Home in Nellysford

4.99 out of 5 average rating, 100 reviews

Glass House | Mountain & Water Views @ Wintergreen

Jul 27 – Aug 3

G$120,662 GYD per night
Guest favorite

Home in Roseland

4.9 out of 5 average rating, 127 reviews

Charming Farmhouse in a great location!

Mar 9 – 16

G$39,666 GYD per night
Guest favorite

Home in Wintergreen Resort

4.95 out of 5 average rating, 193 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Jan 10 – 17

G$46,900 GYD per night
Guest favorite

Home in Greenwood

5.0 out of 5 average rating, 152 reviews

Gorgeous Modern Mountain Home + Blue Ridge Views

Apr 1 – 8

G$115,733 GYD per night

Ski-in/ski-out vacation rentals in Wintergreen

Superhost

Condo in Wintergreen Resort

4.9 out of 5 average rating, 103 reviews

All season 3bd/3ba ski out/in - Location & Views!

Dec 14 – 21

G$60,052 GYD 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 14 – 21

G$20,774 GYD per night
Guest favorite

Apartment in Wintergreen Resort

5.0 out of 5 average rating, 30 reviews

Mountain View Nest

Sep 12 – 19

G$33,000 GYD per night
Guest favorite

Home in Wintergreen Resort

4.92 out of 5 average rating, 26 reviews

Top of the Lift Mountain Getaway

May 2 – 9

G$24,309 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.97 out of 5 average rating, 38 reviews

Cozy little condo, near slopes.

Jun 10 – 17

G$23,334 GYD 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 11 – 18

G$23,356 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 42 reviews

Mountain condo! - Close to everything!

May 16 – 23

G$23,795 GYD per night
Guest favorite

Condo in Wintergreen Resort

4.98 out of 5 average rating, 83 reviews

Mtn/Firework Views ~ King Suite ~ Pet Friendly

Sep 17 – 24

G$29,952 GYD 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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