Holiday houses in Esmont

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Family · Location · Comfort

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!

Family · Location · Getting around

Lux Country Retreat minutes from Charlottesville!

Located just off route 29 this private luxury retreat with surrounding 2 acre fenced yard is one mile from Pippin Hill Farm & Vineyard and only 15 minutes from UVA/Charlottesville. You will find this home spacious, bright and airy, perfect for entertaining groups or families. The house is completely equipped with everything you may need to host the perfect getaway! Nearby attractions: Pippin Hill, Albemarle Ciderworks, Ragged Branch Distillery, Potter's Craft Cider and Charlottesville!

Family · Location · Heating

Riverview at Belle Meade Farm

Escape to Belle Meade Farm, a magnificent 106-acre estate overlooking the James River, once owned by Thomas Jefferson's family. Nestled in the serene countryside, the property is just a mile away from historic downtown Scottsville, a short 25-minute drive to Charlottesville, and near many wineries and breweries. Experience the ultimate outdoor adventure by indulging in a plethora of activities, including petting the cats and dogs, catch and release fishing at our pond, or tubing the river!

Location · Family · Indoor spaces

Terrell House, ca 1850

This ca 1840 house, listed on the National Register of Historic Place as part of the Scottsville Historic District, has been completely renovated. It is located in historic Downtown Scottsville. Within walking distance are four restaurants and a brewery. A grocery store and other restaurants also a short drive away. A nature area with trails is also nearby. It has a kitchen, dining and living area. WiFi. If this house is already reserved, I have other properties that could be available.

Location · Family · Outdoor spaces

Scottsville Downtown Bungalow

Stay in downtown Scottsville. I try to accommodate early check ins or late check outs if requested. The house is neat and clean with central heat and air on a quiet side street. Have fun on the river tubing & kayaking. Walk to Van Clief Nature area, hiking trails, river, brewery & restaurants. It's about 20 miles from UVA and Yogaville & only a short drive to several wineries in the area. The covered front porch has a patio set for 4. Due to allergies, I am unable to accommodate pets.

Family · Location · Bathroom

The Butler’s Cottage At Chester

Sorry for the increase in pricing as Airbnb has rolled their guest fees into our daily rate instead of charging separately. Overall, total costs are the same as before this change. Situated on one of the six historic properties in Scottsville, Chester and its seven-acre setting evokes a feeling of serenity and charm for all those who visit. The main house, built in 1847 and later expanded, still exudes the charm which would have greeted guests arriving in carriages 179 years ago.

Location · Family · Getting around

Rare Find: Private Animal Sanctuary & Tiny Cottage

For animal lovers seeking an exclusive and unique getaway, this boutique Airbnb in Scottsville offers a tranquil escape where guests can unwind in nature and connect with the sanctuary’s resident animals. Recognized by Northern Virginia Magazine, Trips 101, and Trips to Discover as one of Virginia’s most distinctive stays, this thoughtfully curated retreat features cozy furnishings, charming handcrafted details, and an expansive window that showcases views of the animals.

Location · Value · Solo travel

Small cozy Cabin in the foothills! Dogs welcome!

Escape to this private guest cabin for two in the rolling hills of Esmont, just outside Charlottesville and Virginia wine country. Set on 60+ acres of peaceful farm and woods, this quiet retreat offers privacy, wildlife, and open skies. Walk over two miles of private trails (when open) and unwind by the fire pit under the stars. Perfect for a romantic getaway or Blue Ridge escape. No cleaning fees—please tidy up. Dog friendly with a $50 NON-REFUNDABLE fee; dogs must

Family · Value · View

5 King Beds | Sleeps 18 | Pickleball | Brew Trail

Welcome to our spacious six-bedroom retreat, transformed from a large shop into a unique, comfortable living space. Seamless indoor/outdoor living with an industrial garage door, inviting seating areas, and king-sized beds in 5 bedrooms make this the ideal getaway with friends and family. The bunk room comes with two arcade games, and the highlight is the pickleball court, outdoor kitchen, and large gorgeous pergola, ideal for relaxing and taking in the outdoors.

Location · Family · Outdoor spaces

Peaceful Cottage

Wineries, Cideries and Breweries close by. Convenient to Nellysford, Wintergreen and all Charlottesville has to offfer - 3mi Walton’s homestead. Sightseeing, Beer and Wine trail, and Historical Landmarks Very close to the James River Runners tubing and canoeing activities. Old town of Scottsvilles is 9miles away and there is River Rafting company and plently of local eating and a brewery.Pet friendly & fee Type of pet &size requested

Location · Value · Quiet

10 Vineyards Within 10 Mi, EV charger & Mini Goats

Upscale boutique Carriage House on a 25-acre farm in Charlottesville Wine Country. Minutes from top vineyards, this light-filled retreat features elegant rustic design, new furnishings, and spa-like comfort. Enjoy visits with Nigerian dwarf goats and free-ranging chickens. Perfect for romantic getaways or remote work, with WiFi, cozy touches, and the beauty of nature all around. Tesla wall connector charger available for guests.

Family · Location · Checkout