House holiday rentals in Roseland

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

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.

Fire pit with MTN views! Summer fun! Nelson 151.

Dancing Bear Lodge is a cabin located in Roseland, VA. It is just over 2,000 square feet, which makes it a spacious size for hosting larger groups of up to 10 people. If you are looking for an "off the grid" experience on 38 acres with a spectacular mountain view, this place is for you! The property is a nice balance of seclusion while still having the comfort of modern amenities and prime location. Follow along with our adventures on IG @MapleCreekProperties and FB at Maple Creek Properties!

Close to hiking! | 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.

Mountain Mama- Amazing Views! + Hot Tub!

MOUNTAIN MAMA - The home for gorgeous Blue Ridge Mountain views : ) Situated on a graceful 26 acres minutes off Rt. 151, our mountainside home is nestled within the beautiful Rockfish Valley and offers incredible views from every window in a truly unique and newly renovated home. Enjoy sunsets over 3600’ Humpback Mountain due west and sunrises lighting up the valley ridges. If you need time to be inspired by nature’s beauty, this home offers a rare breath of fresh air! Book your stay today!

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

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!

Creekside Retreat | Fire Pit + Big Fenced Yard

Wake up to the sound of the creek and end your evenings around the fire-pit in your fully private, fenced yard. Bear Creek is a peaceful, private Blue Ridge retreat designed for couples, families, and pet-friendly getaways. Inside enjoy three comfortable bedrooms, an open living space, and direct access to a gently babbling creek just steps from the backyard. Minutes to Crabtree Falls, the Appalachian Trail, and Nelson County wineries--yet tucked away in a quiet, relaxing setting.

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

Escape to a spacious, colorful home off the Brew Ridge Trail with oversized windows, mountain views, and plenty of room for groups or couples. Cook in a stocked kitchen, then relax by the fire pit or grill out and unwind on the deck while the dogs enjoy the fenced in yard. Accessible bedrooms and bathrooms on the main floor make it easy for everyone to enjoy. Perfectly located near Wintergreen Resort, Skyline Drive, breweries, wineries, vineyards, hiking, biking, and golf.

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!

The Brew Ridge Trail's Most Unique Home. Sleeps 12

"Guest Favorite" Top 5% of Homes on AirBnB. Rated 4.96★ by 100's of guests. Dogs welcome! 42x SuperHost property. Your Brew Ridge Trail Adventure starts here. Afton’s top-rated Airbnb, this bright, spacious 3,300 sq ft home was extensively renovated in 2026 with brand-new amenities. Minutes from Wintergreen, the Brew Ridge Trail, breweries, wineries, hiking, golf, and the Blue Ridge Parkway. Perfect for friend getaways, reunions, and unforgettable weekends.

Fleetwood (c. 1809) - A renovated landmark

Built in 1809 as a country home and renovated in 2019, Fleetwood is great balance of old-world charm and modern convenience located right in the middle of Nelson County's music, craft beer, and adventure destinations. Fleetwood sits atop a private bluff of solid rock overlooking the Tye River, with beautiful views of the Blue Ridge Mountains. When you visit you’ll feel that people have enjoyed this special spot for thousands of years.