House vacation rentals in Wintergreen Resort

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Top-rated house rentals in Wintergreen Resort

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Guest favorite

Home in Wintergreen Resort

4.97 out of 5 average rating, 153 reviews

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

Completely renovated, 3 BR/2BA chalet, located on Lower Tyro slope, just below Tequila. Rustic decor, fully stocked kitchen, high end appliances, granite counters. Open floor plan, walls of windows, mtn views. Beautiful stone fireplace, ample comfortable seating. 2 main floor Masters, each w/King bed, TV, luxurious bedding. Loft is a dedicated kids space: 2 sets of bunks, daybed w/trundle, TV & PS4. Gas grill, 6 person hot tub. Perfect ski home to host 2 Families, or a romantic couple's getaway.

Sep 25 – Oct 2

R5,809 ZAR per night

Guest favorite

Home in Vesuvius

4.96 out of 5 average rating, 171 reviews

Mountain-view haven: hot tub & game room

A truly one of a kind experience welcomes you at Harvest Moon Lodge and Retreat. Nestled high on 9.2 acres in the heart of the Blue Ridge Mountains, Harvest Moon is close to the best the Blue Ridge and Shenandoah Valley have to offer. Enjoy spectacular views from every corner of the Lodge, not to mention the two enormous front porches! With a seven person hot tub, fire pits, pool and air hockey tables, grill, DirecTV and more, Harvest Moon is fully equipped for families and friends of all kinds.

Dec 20 – 27

R11,979 ZAR per night

Guest favorite

Home in Wintergreen Resort

5.0 out of 5 average rating, 28 reviews

Cozy Chalet | Hot Tub | King Beds | Dog Friendly

Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

Sep 8 – 15

R3,604 ZAR per night

Guest favorite

Home in Nellysford

4.99 out of 5 average rating, 103 reviews

Glass House | Mountain & Water Views @ Wintergreen

This custom home at the base of Wintergreen is located 40-minutes from Charlottesville. The waterside setting offers views from living, primary bedrooms, decks and porches, as well as upstairs bedroom and balcony. Large glass walls and sliding doors ensure connection with the landscape. A two-person master-bathroom shower with views of the pond is a key feature of the home's sleek and minimalist design. The home is off of the Rte. 151 beer/wine/distillery trail and nestled beside a golf course.

Nov 5 – 12

R15,538 ZAR per night

Superhost

Home in Roseland

4.88 out of 5 average rating, 114 reviews

Hiker’s paradise with NEW HOT TUB!

Wintergreen mountain house located yards from the Blue Ridge Parkway & Appalachian Trail! The house is 3 stories with several porches, 3 of them are private. It has a lighted circular driveway. The top floor has two bedrooms & one large bathroom. The main living area is on the second floor with a master bedroom. The bottom floor has another master bedroom, & additional bunk room. The kitchen has a 10-seat kitchen table. After a long day enjoying the outdoors, relax by the fireplace or hot-tub!

Mar 17 – 24

R7,013 ZAR per night

Guest favorite

Home in Greenwood

5.0 out of 5 average rating, 154 reviews

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain retreat nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious master suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and plenty of games.

Jan 21 – 28

R9,939 ZAR per night

Guest favorite

Home in Wintergreen Resort

4.91 out of 5 average rating, 66 reviews

*Have cabin fever at home?* Come enjoy our cabin!

Cozy family cabin that sleeps 8 (King, Queen, 2x Twin bunks) tucked away on a quiet cul-de-sac is the ideal mountain getaway offering the best of seasonal activities like hiking, fishing, swimming, golf, brewery tours, skiing, etc. 2-minute drive to Wintergreen Resort, yet also conveniently close to the "Valley", where restaurants/breweries are. Soaring cathedral ceilings with open concept and lots of light, WiFi, smart TV, fully-equipped kitchen, wood-burning fireplace, DVDs, games, & more.

Apr 14 – 21

R2,461 ZAR per night

Guest favorite

Home in Wintergreen Resort

4.95 out of 5 average rating, 194 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

Your mountain adventure awaits at Saltbox, an inviting, eclectic home at Wintergreen Resort in the Blue Ridge Mountains. Combining modern and vintage decor, plus original art, Saltbox was designed to provide escape, inspiration and fun. Nestled at the end of a quiet cul-de-sac drive, with beautiful woods to explore, it's just seconds from the Resort (skiing, tubing, hiking, dining, spa, outdoor movies and more)! Saltbox is the perfect home base for your next getaway, any time of year!

Dec 1 – 8

R4,012 ZAR per night

Superhost

Home in Wintergreen Resort

4.89 out of 5 average rating, 187 reviews

The Blue Ridge Eagles Nest. Summit of Wintergreen

Separate to an environment at the literal peak of the mtn. Where better to find peace than on a deck with a top of the mountain view of the Blue Ridge? Welcome to our cozy home away from large groups. We are the only home on the Circle and have a full equipped kitchen. A list of available restaurant services that pick up and deliver can be provided in addition to 24/7 emergency medical/critical care responders located on the mtn. Enjoy Nature. Be Healthy. We'd love to have your stay.

Oct 27 – Nov 3

R6,229 ZAR per night

Guest favorite

Home in Faber

4.99 out of 5 average rating, 119 reviews

Buck Creek Lodge (2 bedrooms) Hidden in Blue Ridge

Buck Creek Lodge located on 33 very private acres: ~ Very clean! ~ Cove, creek and mountain views ~ Walking paths through woods and meadow ~ Ample porch for dining, relaxing and viewing ~ Stone-accented designer gardens ~ Secluded and quiet, perfect for wildlife sightings ~ WiFi and a quiet place for work ~ Rural, yes, but so close to so much. ~ Very near breweries, wineries and distilleries. ~ Half hour from Charlottesville, the AT, Blue Ridge Parkway and Wintergreen Resort

Jul 16 – 23

R3,391 ZAR per night

Guest favorite

Home in Wintergreen Resort

4.91 out of 5 average rating, 173 reviews

Weeping Rock Retreat, Wintergreen Resort

Welcome to Weeping Rock Retreat in Wintergreen Resort. This 4 bedroom, 3 full bath home is certain to fit your individual or family needs. Tucked away on a hill off a quiet street is sure to give you a peaceful retreat to enjoy your vacation. Our home is located walking distance from the Upper Shamokin Trail which features a great scenic waterfall and easy trail for family. Great for large or multiple families and a short drive to the ski slopes.

Feb 23 – Mar 2

R4,935 ZAR per night

Guest favorite

Home in Shipman

4.88 out of 5 average rating, 117 reviews

The Refuge at Laurel

Enjoy a cozy mountain getaway located in the heart of Nelson County. Perfect for couples, friends, or singles, the Refuge at Laurel is 25 minutes from Charlottesville and a short drive to the wineries, breweries, distilleries, and orchards on Route 151. Take a hike through the mountains on the many trails bordering the George Washington National Forest. Or, work from the home office with included fiber Internet.

Jan 14 – 21

R2,198 ZAR per night