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 Lovingston

4.93 out of 5 average rating, 147 reviews

Three Springs with EV charging station

Beautiful 3-bedroom home outfitted to accommodate a variety of visitors with high-speed internet, 2 large screen TVs, whirlpool tub, hiking, wildlife, and a huge deck. Nestled in a quiet cove in the beautiful Blue Ridge mountains. Located on Nelson's Craft Beverage Trail and a short drive to Charlottesville, Lynchburg, Staunton, Wintergreen, and Skyline Drive. Close to Oak Ridge for music festivals/events. Larger parties, see the Three Springs Plus listing. EV charging available for $20/night.

Guest favorite

Home in Wintergreen Resort

4.97 out of 5 average rating, 176 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.

Superhost

Home in Roseland

4.87 out of 5 average rating, 134 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 Afton

4.99 out of 5 average rating, 145 reviews

Clean family-friendly 5br for wine country getaway

Come to Sunnyside! A new 5 bedroom home with game room, hot tub, and space for 12 people on 4 acres on a private farm road. Just off the infamous Route 151, or "Brew Ridge Trail", you are RIGHT in the middle of the action: 7 minutes to 10 wineries / breweries, 5 minutes to the nearest family farm or golf course, 10 minutes to Skyline Drive with PLENTY of places to hike, and 25 minutes to skiing at Wintergreen. You are surrounded by jaw-dropping mountain views/sunsets that surprise every guest.

Guest favorite

Home in Afton

4.97 out of 5 average rating, 342 reviews

Spacious Estate Home on the Brew Ridge Trail

Looking for a unique pet-friendly stay that accommodates up to 12? You’ve found it in amenity-rich Boogie Nights Manor a wildly spacious, 4,000+-sq-ft home on 3+ acres where every room is a feast for the eyes, filled with art and artifacts. Whether you’re an outdoor enthusiast, fall-foliage viewer, or fan of craft beverages planning to visit wineries, breweries, and distilleries on the Brew Ridge Trail, you’re unlikely to ever find a rental like this one! You’ll love the Central-VA location.

Guest favorite

Home in Greenwood

5 out of 5 average rating, 176 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 Nellysford

4.99 out of 5 average rating, 130 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 Afton

4.95 out of 5 average rating, 222 reviews

CritzerHouse - on 151- Walk to the Brewery!

We are right on the main route of 151, but set back off the road . This 2,000 sqft house is walking distance to Blue Mountain Brewery and only a stones throw to the many Wineries, Breweries, Cideries, and Distilleries Nelson has to offer. We are 20 minutes from Wintergreen Ski Resort, 15 minutes from Waynesboro and 20 minutes to Charlottesville. We are 5 miles from the Blue Ridge Parkway / Skyline Drive for Hiking /Cycling. This home has fiber Internet ( 1 Gbps) for working trips.

Guest favorite

Home in Afton

4.97 out of 5 average rating, 117 reviews

Modern Home on 25 Acre Ridgetop with Amazing Views

Architect-designed 2,900 sf home sits on a high ridge. Main living space optimizes dramatic views of Humpback Mountain. Covered porch wraps around entire second floor. Situated on 25 private acres within the George Washington National Forest. House is only 1 paved mile to Rockfish Valley Road, Rt. 151 (aka the Red, White and Brew Trail). 30 minutes from Charlottesville, Va. Close to breweries, wineries, hiking & excellent restaurants.

Superhost

Home in Lovingston

4.85 out of 5 average rating, 297 reviews

Secluded Mountain Cabin w/ Pool, Trails & Winery ❤️

Nestled in Mountain Cove with views of Mountain Cove Winery, this property offers 100MB high-speed internet, adjacent to 800 acres of hiking trails. With an in-ground pool, deck, and firepit area, it's 35 minutes from Wintergreen, surrounded by wineries, breweries, and horseback riding. Ideal for creating memories. Note* Pool is not heated and closed when it’s cold. Ask before booking if the pool is open if you plan to swim.

Superhost

Home in Waynesboro

4.83 out of 5 average rating, 108 reviews

Hot Tub - Fire Pit - Game Room

Howdy! Nestled perfectly between the North Terminus of the Blue Ridge Parkway, the entrance to Skyline Drive, all of the Afton wineries, the Beerwerks Trail, Wintergreen Resort, and Downtown Waynesboro, this four bedroom house with a fully stocked game room, two patios, a fire pit, and hot tub is the perfect spot to relax after a long day of enjoying the Shenandoah Valley.