House vacation rentals in Wintergreen Resort

Find and book unique houses on Airbnb

Top-rated house rentals in Wintergreen Resort

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Home in Wintergreen Resort

5 out of 5 average rating, 102 reviews

Cozy Chalet | King Beds | Fireplace | Hot Tub

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.

Top guest favorite

Home in Lovingston

4.93 out of 5 average rating, 150 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.

Top guest favorite

Home in Afton

4.98 out of 5 average rating, 101 reviews

Hot Tub, Firepit, Foosball, Walk to Coffee & Park!

Welcome to Creekside! Just minutes from the best wineries and breweries, it’s the perfect getaway to explore the 151 Brew Trail, Wintergreen Resort and the Blue Ridge Parkway. Enjoy mountain views and privacy in the hot tub. Roast marshmallows around the huge fire pit. Cozy up on the large sectional sofa in front of the 65" 4K TV. Cooks will enjoy the spacious and fully equipped kitchen! All beds have new memory foam mattresses. Fast Wi-Fi for remote work! Level 2 EV charger located in driveway.

Guest favorite

Home in Wintergreen Resort

4.97 out of 5 average rating, 195 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

4.88 out of 5 average rating, 142 reviews

Hikers, Spring has sprung & ready for you to come!

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, 153 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.

Top guest favorite

Home in Nellysford

4.99 out of 5 average rating, 135 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!

Superhost

Home in Wintergreen Resort

4.86 out of 5 average rating, 107 reviews

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $150. 8min walk or 3min drive to ski.

Guest favorite

Home in Nellysford

4.97 out of 5 average rating, 136 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!

Top guest favorite

Home in Lovingston

5 out of 5 average rating, 178 reviews

Ms Maria's Place - make yourself at home, relax!

Newly renovated house on a quiet cove road .2 miles off of Rte 29 between Charlottesville and Lynchburg. The property includes high speed 100 Mbps Internet, a 65" Smart TV, gas grill, and a fire pit with outdoor seating. Enjoy visiting the local restaurants, orchards, wineries, and breweries. You will be a short drive from hiking Crabtree Falls, the Blue Ridge Parkway, Humpback Rock, Wintergreen, and James River State Park. The Lovingston Winery is just minutes down the road!

Top guest favorite

Home in Schuyler

4.93 out of 5 average rating, 180 reviews

HeartRock Home Stay or Retreat

Welcome to HeartRock. Enjoy our ready made late 21st century rustic homestead. The space is old and humble yet full of life! Surrounded by edible, medicinal, and floral gardens will have you catching the breath you’ve been waiting for. No kidding! Plus the quite afternoon atmosphere tends to hold sunsets and starry nights where by chance your pace has simply slowed down. Lastly we are anywhere from 15-30 mins away from vineyards breweries hiking and the Rockfish River.

Superhost

Home in Crozet

4.9 out of 5 average rating, 101 reviews

Beauchamp House 2 BD Fishing Hiking Lake

The Beauchamp House is in the Blue Ridge Mountains of Virginia, near the Shenandoah National Park and Charlottesville, Va. Ideal for couples, friends and families. One pet welcome with additional $100 fee. Enjoy 129 acres with hiking trails, small lake, free mountain bikes, canoes, fishing. Wineries and fine dining nearby. Includes high speed internet and Roku TV. House has a separate basement apartment with a separate entrance and driveway.