House vacation rentals in Wintergreen

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Top-rated house rentals in Wintergreen

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Guest favorite

Home in Vesuvius

4.94 out of 5 average rating, 196 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

4.97 out of 5 average rating, 173 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 Nellysford

4.98 out of 5 average rating, 122 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.

Superhost

Home in Roseland

4.87 out of 5 average rating, 131 reviews

Ski season coming up Soon Book Hiker’s paradise!

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!

Guest favorite

Home in Greenwood

5 out of 5 average rating, 173 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 Nellysford

4.99 out of 5 average rating, 120 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

4.95 out of 5 average rating, 208 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 Nellysford

4.99 out of 5 average rating, 127 reviews

“Small" House/Peaceful/Breweries/Hikes/Wineries

The Small House is anything but small when it comes to comfort and relaxation. It is located in the heart of Nellysford near a local grocery store and restaurants. Close to many hikes, the Blue Ridge Parkway, the AT, wineries, cideries, and breweries! The property includes a deck, outdoor fire pit, grill, and 11 acres to explore. At the very back of the property is 600 feet of private river/creek access. The perfect spot to fish, picnic, read, and/or let the kids cool off and play!

Guest favorite

Home in Lovingston

4.95 out of 5 average rating, 199 reviews

Private, Covered, Heated Year-Round Pool & Hot Tub

Experience the Blue Ridge Mountains and country life of central Virginia and enjoy everything Nelson County has to offer. The Cottage on the Knoll is a comfortable 3br/2bth that’s centrally located in Nelson County, offering the perfect mix of modern comfort and country charm. The Nelson 29 and Nelson 151 craft beverage trails await you, while plenty of hiking, fishing, and mountain views will appease any outdoor recreation lover or nature enthusiast, making it the perfect getaway.

Guest favorite

Home in Roseland

4.98 out of 5 average rating, 144 reviews

Dove's Landing at Wintergreen Resort

Located in the heart of Wintergreen Resort with all the family-friendly activities that make the Mountain famous - great restaurants, spectacular views, skiing, hiking, golf, and spa. Due to increased demand for bringing along a fur baby, we now allow 1-2 dogs for a $150 flat pet fee. If you have a (calm, well behaved) pup that you would like to bring along, she/he is welcome! Please send inquiry for specific questions about Wintergreen amenity availability.

Guest favorite

Home in Afton

4.89 out of 5 average rating, 386 reviews

Modern Barn Escape+Brew Ridge Trail+CouplesRetreat

Recently refurnished to a high standard. The current Barn features a gourmet/chefs kitchen, full bathroom with standup shower, WiFi, 55" Smart TV with Netflix, Air con, fire pit, grill, patio and plenty of space to sleep 6. Enjoy your time home on the Farm! Private outdoor area, parking & self check-in. Also boasts some of the best views along the Brew Ridge Trail. Sit on your patio & watch the sun set over Humpback rock and the Blue Ridge Mountains.

Guest favorite

Home in Shipman

4.86 out of 5 average rating, 130 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.