Holiday rentals in Dillwyn

10 Acre Wilderness Paradise!

Welcome to 🐻Lazy Bear Lodge🐻!! Escape to this luxurious, secluded 10-acre Wonderland! Vast space to sleep 12, this stunning retreat lets you unwind & enjoy the great outdoors. Relax on the expansive wrap-around deck, by the fire pit, or explore the trails. Enjoy the arcade, billiards, & outdoor games! LBL has 3 levels, 3 spacious bedrooms, & 3 bathrooms. Enjoy a fully equipped kitchen & dine in the elegant dining area or on the deck with breathtaking views of the surrounding nature.

Caryn’s Cozy Cabin Hampden-Sydney

Beautifully restored spacious and peaceful log cabin with curated finishes, furniture, and fixtures throughout. Kitchen layout, along with adjoining sunroom and deck are perfect for family gatherings. Incredible location. Less than 4 miles from Hampden-Sydney, Longwood University, Downtown Farmville, Appomattox River, High Bridge Trail, and Dining Shopping. 4 bedrooms -2 queen beds and 4 twin- 3 full bathrooms. Central air, fireplace, WiFi, 3 TVs, and washer and dryer. Managed locally

The Hide-A-Way

Follow a long gravel driveway before you can view this comfortable house in the country. This house is 12 easy miles from the Town of Farmville and all it has to offer. Longwood University and Hampden-Sydney College is near by. Visit High Bridge State Park for hiking and Greenfront is a shopping destination. Lots of dining options will appeal to every taste and plenty of other activities to enjoy in this area. There is no phone-internet or satellite at The Hide-A-Way, Cell phones do work.

La-de-da studio near James River and Wineries

Welcome to La-de-da! We are located in beautiful, rural Howardsville, Virginia with convenient access to all the recreational amenities the James River has to offer. We are a VERY scenic 35 minutes to Wintergreen, all the wineries, breweries, distilleries and orchards in the region and great hiking trails! We are far enough outside of the cities of Charlottesville and Scottsville to provide peace and quiet, but just a scenic 20 minute drive to Scottsville and 40 minutes to Charlottesville.

The Cottage at Hardware Hills Vineyard

Head for the Hills! The Cottage at Hardware Hills Vineyard sits atop the property alongside the main estate house. Bask in Virginia sunsets over the vines. Take a short hike down to the Hardware River where you can dip a toe in or try your hand at fishing. On weekends, you have a family-owned winery right in your front yard to stroll down and sit by the vines to enjoy delicious wines. Centrally located to many wine trail attractions and all that the Charlottesville area has to offer.

Shepherdess Cottage

Charming cottage located in Scottsville, Virginia on a 93 acre sheep farm. It is located 19 miles from Charlottesville. The Shepherdess Cottage is tiny, relatively private and offers beautiful views. We are a working farm so you may encounter us, but will respect your privacy as much as we can. You are welcome to "free range" with our sheep and enjoy exploring the property. Sometimes our lambing season (pretty much year-round) will offer bottle babies that you can feed and cuddle.

Whisper Creek Lodge! Lower Level Suite!

Whisper Creek! Located in the foothills of the Shenandoah Mountains. This Lower Level Suite will provide you and friends with the perfect place for back woods peace and quiet. Located one hour from UVA, Wintergreen, numerous Craft Beer Pubs and Wineries. This includes numerous choices for hiking. If canoeing and kayaking is your interest, I am located a short distance from several launch sites. I am willing to shuttle vehicles and assist in getting you where you wanna be.

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.

Convenient Rustic Cabin near Wineries

I’m located 6 miles from Scottsville, 15 miles from Charlottesville, 25-30 minute drive. A pasture of cattle is not too far away you can hear the mooing at times and see sightings of deer quite often. It’s a private and quiet location. Two large rivers, James and Rivanna offer recreational activities. Rustic cabin, country located. Clean and cozy with a well stocked kitchen with all your cooking needs. If not, leave suggestions on what is missed. Thank you.

BrightEyes Alpaca Retreat Farmville ,Virginia

Separate apartment ABOVE detached garage; Modestly equipped kitchen. KING bed, sitting area & electric fireplace. TV in living room. No WiFi. Your HOTSPOT works great here. PET FREE indoor/outdoor. *Pet free/NO pets allowed* , no exceptions. NO smoking (any device/format)on the premises. Max 3/No children under 5. Apartment access is thru INDOOR garage stairs;not recommended for individuals with mobility issues. No entrance by deck (there are no lights).

The Lake House

Enjoy nature in this lakefront 3 bed/1.5 bath retreat. This house is set off the road in a very serene and rural area, yet you are only a short drive away from many conveniences. Less than 5 miles from Downtown Farmville, restaurants, GreenFront, and Longwood University. About a 20 min to Hampden Sydney. This is the perfect place to disconnect from the outside world and relax dockside. *Please read all details below*

Sunflower Cottage

Peaceful 350-acre cattle farm/estate in 4.5 miles of gravel trails—just 17 minutes from Scottsville and 35 minutes from Charlottesville. Visit historical sites including Jefferson's Monticello and James Monroe's Ashlawn Highland. Enjoy kayaking on the James River and multiple award-winning wineries and breweries within minutes of your stay. Equine enthusiasts welcome—a fenced yard for the pup.