Wintergreen Resort house rentals

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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, 159 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.

Guest favorite

Home in Vesuvius

4.96 out of 5 average rating, 176 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.

Guest favorite

Home in Wintergreen Resort

5 out of 5 average rating, 40 reviews

Cozy Chalet | King Beds | Hot Tub | 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.

Guest favorite

Home in Nellysford

4.99 out of 5 average rating, 112 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.

Guest favorite

Home in Greenwood

5 out of 5 average rating, 160 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.

Guest favorite

Home in Wintergreen Resort

4.87 out of 5 average rating, 38 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

4min drive to Wintergreen skiing. Secluded farmhouse-style with views in every room. Hiking, breweries/vineyards, fishing, and skiing. Two bedrooms and two bathrooms on first floor. One bedroom plus full bath and loft on 2nd floor. ★Hot Tub ★EV Charger ★Mountain AND golf course views ★Sleeps 9: K, Q, 2x S, 3x S ★Dining table for 8 + 4 @ breakfast bar ★Wrap-around deck ★Fireplace ★Desk ★Family-friendly ★Gas grill and firepit Seasonal pool/tennis access included. Resort access not included.

Guest favorite

Home in Nellysford

5 out of 5 average rating, 105 reviews

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

Guest favorite

Home in Wintergreen Resort

4.9 out of 5 average rating, 20 reviews

Beautiful Retreat at Wintergreen Resort

Beautifully renovated getaway on Wintergreen Resort. This dog-friendly two-bedroom condo features four beds and two bathrooms. It’s a great retreat from the hustle and bustle of the resort at the end of each day’s adventures. If we can do anything to make your stay more enjoyable, don’t hesitate to reach out, and please kick back and relax and enjoy all that Wintergreen has to offer! Note: There is a shuttle that stops in front of Tanners Ridge for the ski slopes on the weekends only.

Guest favorite

Home in Wintergreen Resort

4.95 out of 5 average rating, 198 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!

Guest favorite

Home in Faber

4.98 out of 5 average rating, 128 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

Guest favorite

Home in Wintergreen Resort

4.89 out of 5 average rating, 27 reviews

Creek Hot Tub Pool Tennis Golf Hiking King Beds

Nestled aside a perennial mountain stream, your cozy house is the perfect place to getaway with your family or friends. Located very close to ski slopes, hiking, wineries, and golf courses. Enjoy the outdoors skiing or hiking during the day - or just relax on the deck listening to the sound of the spring water. In the evening, drink cocoa by the fire, snuggle up and read a book, or relax in the hot tub. Great for couples and families alike. 5min dive to skiing at Wintergreen

Guest favorite

Home in Wintergreen Resort

4.9 out of 5 average rating, 31 reviews

Hot Tub Mntn Views Pool Tennis Golf Hiking 52"HDTV

4min dive to slopes! Impressive 3-story mountain estate. Ideal for family retreats and adventurous getaways. Features HOT TUB. Wineries, breweries, farmers market, and walk to hiking trails. ★Comfortably sleeps 10: K, K, Full, Twin bunk beds, Sleeper sofa in loft ★Great room with stone fireplace ★Dining table for 8 ★FAST Wi-Fi ★Two 52" HDTVs ★Wrap around decks ★Fire Pit ★Hot Tub ★Plenty of parking Seasonal outdoor pool/tennis access. Resort access not included.