Holiday rentals with a kayak in Nelson County

Very Private Cabin on 100 Acres - Howl at the Moon

"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

Spindle Hill Farm’s Schoolhouse | Fire pit, Pond

A solar-powered 1932 schoolhouse on 50 acres of farm & forest— huge original windows, hardwood floors, two ponds with a dock, and a kitchen stocked like it means it. Three bedrooms, two colorful bathrooms, sleeps six. Fireplace. Private hiking trails through the woods, a gas fire pit, and charcoal grill. Fast fiber internet. EV charger. Hidden and private, but 2 minutes from Devils Backbone and right in the heart of the 151 Brew Ridge Trail. An honest-to-goodness one of a kind. Come see it.

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 are welcome. Wheelchair accessible rooms are available for people with disabilities. Perfect for longer stays, family reunions, retreats, and small weddings.

Treetop Sunset Deck, 2 Upscale King Bedrooms

Enjoy a top-floor mountain sanctuary at The Haven at Wintergreen! Overlooking scenic treetops and the 18th green, this private end unit features 2 king bedrooms with plush linens, a cozy stone fireplace, full kitchen, and a deck with stunning sunset views. Walk to hiking trails, Founders Overlook, and The Spa at Wintergreen, or hop on the seasonal ski shuttle. Minutes from the Blue Ridge Parkway, local wineries, and craft breweries. Reconnect with nature and find your mountain reset here!

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!

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

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.

Historic 1870s Log Cabin near Charlottesville

Large Historic, Restored 1870'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.

Parr's Camp - Nothin' Fancy Fish Camp

Experience the Blue Ridge Mountains in a 1940’s fishing cabin! Guests adore Parr's Camp-it's rustic outside & restored charm inside. A private pond & the Tye River flow steps away for you to enjoy the ever-changing mountain stream. Our family friendly cabin allows children areas to explore nature & enjoy marshmallows over the campfire. We have enhanced our cleaning procedures & taken care to properly disinfect between reservations.

Riverfront Cottage

This peaceful riverfront cabin features private access to the Rockfish River nestled in the foothills of the Blue Ridge Mountains. You can kayak for miles along the Rockfish, replenish with an outdoor shower, and relax into the tranquility of the large screened porch. Enjoying the outdoors here is easy. From the nearby Appalachian Trail and Blue Ridge Parkway to the comforts of home at this charming gem on the edge of the wild.