Holiday rentals in Massies Mill

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

Stargazing on 12 Acres: Hot Tub 55"TV Fire Pit

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

Bear Creek Inn 3 BR House Creekside

3BR HOUSE, QUIET CREEKSIDE RETREAT, PET FRIENDLY, FENCED YARD ENTIRE 3 BR mountain home with a large fenced backyard and a babbling creek—perfect for couples, families, and pets. Minutes to Crabtree Falls, the Appalachian Trail head, and George Washington National Forest. Unwind in nature, then explore Nelson 151 breweries and wineries or head to Wintergreen Resort just 12 miles away. Space, privacy, and adventure all in one unforgettable stay. Pet fee auto added when indicated at booking.

Tiny Log Cabin

This tiny hand-hewn log cabin is a perfect, peaceful, and relaxing way to unwind and reconnect with your loved one or have a personal retreat for yourself. Nestled in the Blue Ridge Mountains on 300 acres of private land with plenty of room to explore and enjoy the wild life. Come witness the brilliant night sky lying in an open field with no city lights to diminish the experience. Minutes to Wintergreen Resort, the Appalachian Trail, Sherando Lake, 4 breweries, 6 wineries, and 3 cideries.

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

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!

Dogwood Suite at Open Heart Inn

Welcome to your country retreat! This unique section of the farmhouse was originally built in 1840, and features a cozy, king-sized bed. Relax on your private front porch, enjoy the views from the back patio, explore our 10 acres of farmland, take in the dogwoods and beautiful flowers, and get away from it all! Minutes from the Appalachian Trail, Devil's Backbone, and much more-- we are perfectly located to explore the trails, breweries, and wineries of scenic Nelson County.

Little Cabin in the Woods is quiet and secluded!

Enjoy our rustic, cozy, historic log cabin in the woods on 21 acres with two streams and a little meadow. The logs, from the 1800's, were reconfigured 17 years ago combining a rich history with high speed internet and modern amenities. Sink into the luscious bed with totally organic sheets, mattress topper, and pillows. Take a walk on the original wagon train road down to a stream or bath your senses in the majestic view of Jump Mountain from the meadow.

The Humble Abode Camp

The Humble Abode is a secluded CAMP & offers a scenic view of DePriest Mountains range and is the perfect place to un-plug & disconnect to reconnect!! Our private and secluded camp provides with spectacular mountain views and a NEW OUTDOOR Shower!! with pressurized ambient water temperature, spacious deck, covered porch, double bed, hammock, yard to play croquet/corn hole, private port-a-potty, charcoal grill, and a solo stove firewood pit.

Little is Much - Tiny on the Tye

Enjoy the peaceful sound of flowing water when you stay in this Riverfront Tiny House, located right beside the Tye River in Nelson County, VA. While staying enjoy fishing the trout stocked river, hiking the Appalachian trail or Crabtree Falls, many attractions at Wintergreen Ski Resort, beauty of the Blue Ridge Parkway, hunting in the George Washington National Forest and much more!