Holiday rentals with a kayak in Nelson County

Wintergreen High-Ceiling Chalet with Jacuzzi/Sauna

Beautiful home for a getaway in the Blue Ridge Mountains! Cozy and spacious chalet that is great for a relaxing time or adventures with friends or family. Close proximity to the Wintergreen Resort Ski Lift, Spa, Aquatic Center, and hiking trails. 3 level house, living room with 2- Story vaulted ceiling and wood-burning fireplace. Five bedrooms including master. Sleeps 11: 4 Queen, 3 twin beds. Basement with pool table, wet bar and gas fireplace. Lower deck with Hot Tub and Barrel Sauna 6 person.

Spindle Hill Farm’s School House ~ Firepit, Pond

Historic charmer with great views, the 1932 School House on Spindle Hill Farm sleeps up to 6, with private ponds & the best location in Nelson County, off hwy 151, the heart of Va’s wine & brew country. Antiques, art, books galore. 8 minutes to the Appalachian Trail and Wintergreen resort ⛷️. An easy walk to public trails and Devil’s Backbone Brewery & Bold Rock Cider. High speed fiber internet, gas fireplace, huge windows. Patio, grill, gas fire pit, dock, private forest trails, and EV Charger.

Leaf Peeping Headquarters

This unit is perfectly situated at The Ledges, just a quick five-minute drive to the Mountain Inn. Mountain Dreams is a newly designed, phenomenal condo that offers stunning 180-degree views of Charlottesville, Lake Monocan, the UVA observatory, and ski slopes. Located at the highest elevation, this two-story condo provides a prime location, only 8 miles from Devils Backbone Brewery, Bold Rock or Three Notch'd. Walk conveniently across the street for stone-fired pizza and beer at Fire and Frost.

The Stilt House at Perkins Hollow

Welcome to The Stilt House, where tranquility meets adventure in the heart of nature. Step into the space and be greeted by its charming loft-style design. The main floor features a well-appointed living area with a comfortable sofa, perfect for relaxing after a day of exploration. Ascend the ladder to find a snug loft bedroom, complete with a plush queen-sized bed adorned with soft linens. Natural light floods through the windows, providing stunning views of the surrounding woods and hollow.

Very Private Cabin - H'Owl at the Moon Farm

"Into the forest I go... to lose my mind and find my soul." -John Muir Incredible cabin nestled in the center of 70 very private acres. Relax and unwind to the sights and sounds of frogs, crickets, & owls. Ideal for families and couples. The Cabin offers close proximity to the James River & tubing, UVA, and many wineries. You will see millions of stars and gain the serenity that can only come from nature. The Cabin is also only 20 minutes away from all that Charlottesville has to offer!

James River Cottage with 2 Kayaks to use.

Escape to a tranquil one-bedroom cottage getaway located along the serene James River. This charming retreat offers direct access to the river, allowing you to relax and unwind in a picturesque setting. Enjoy the convenience of a picnic table where you can savor meals or simply take in the soothing sounds of nature. Inside the cottage, you'll find a well-equipped kitchen that invites you to prepare delicious meals at your own pace. The bathroom features a refreshing shower. Kayaks available

SkySpace Sanctuary

This beautiful secluded hilltop home offers breathtaking panoramic views of the Blue Ridge Mountains and the graceful James River under an endless sky. Enjoy quiet, peaceful times alone and quality time with loved ones and friends. Relax in a family hot tub. Prepare meals in the spacious kitchen or grill on the terrace. Children welcome. Wheelchair accessible rooms available for people with disabilities. Perfect for longer stays, family reunions, retreats, workshops and small weddings.

High View Farm | Historic Comfort | Mountain Views

Lovingly maintained and beautifully updated, this 1840s farmhouse is the treasure you’ve been looking for! For an additional fee, add two more houses on the property to accommodate more guests. On over 70 acres, our small herds of Scottish Highland cattle and miniature donkeys graze in green pastures and Virginia woodland. The South Rockfish River and a peaceful pond are perfect for swimming, fishing, and exploring. We invite you to enjoy this slice of heaven in the Blue Ridge Mountains!

Cozy Mountain Cottage

Welcome to your next mountain cottage getaway. This beauty is located in the heart of Afton, Virginia along route 151 known as "Alcohol Alley". Located 2 miles from Blue Mountain Brewery, 3 miles from Flying Fox Vineyard. A 5-minute drive will bring you to a host of wineries, breweries, and distilleries including Veritas Vineyards, Hazy Mountain Vineyards, and Valley Road Vineyards. We love animals so pets are welcome with a $50 additional fee, per pet. Restaurants can deliver!

Restored Double Log Cabin on 400 Mountain Acres

Large Historic, Restored 1880's Log Cabin sleeps up to 15 people. Secluded mountain location, 4 bedrooms, 1 loft, 4 bathrooms. Escape the heat of the city and suburbia for fresh mountain air, mature forest canopy, historic ambiance, stone fire pit surrounded by Adirondack chairs. Coffee klatch with friends and family on the wide open porch, forest bath afternoons, grill and bar-b-que evenings around the fire. Enjoy a special long weekend with family and friends.

Woodson's Mill House

Conveniently located near Charlottesville, Wintergreen, and the Blue Ridge Pkwy, this idyllic Craftsman style home offers the perfect opportunity for couples weekends filled with excursions to local wineries, breweries, and restaurants, or quiet family getaways spent exploring the property's woods, lake, and historic Woodson’s Mill. This property offers the best of both worlds and is centrally located to all that the heart of the Blue Ridge Mountains has to offer.

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~

Bluebird Mountain Home is a beautifully decorated, thoughtfully designed, light filled, cozy house nestled among the trees on Wintergreen Resort. This home offers NO steps from the front drive to the main level master suite and an impressive main level Billiard room and screen porch. Guests have access to the community pool which is a short walk from the house. Relax with tons of books, games, puzzles, or unwind by playing billiards or guitar.