Holiday rentals in Whitesville

Country Charm

This House is located in a quiet neighborhood one block off Main street here in Beaver Dam, KY. Enjoy a nice cozy country home while you visit. It is fully finished so you will feel right home. The property sits on a corner lot with access from both streets. The house has a front porch for lazy evening to catch some fresh air. You can pull right up underneath the carport for easy access to the back door for entry. The home offers a nice yard and fire pit. Food and shopping all minutes away

Cowbell Cottage farm stay

Welcome to Cowbell Cottage, a charming two-bedroom, one-bath retreat on a peaceful working cow farm. Built around an authentic 1800s log cabin, this home is restored with a cozy western theme, blending rustic charm with modern comfort. Relax in the tranquil countryside, where the sounds of nature replace city noise. While there’s no TV to interrupt the serenity, Wi-Fi is available for your convenience. Cowbell Cottage offers a unique getaway that celebrates history, and the beauty of farm life.

Walk in the Woods - Pole Barn, Game-Room, Firepit

If you are looking to unplug, relax, and unwind this barndominium nestled in 93 acres of woods is the place for you. Enjoy the fully equipped kitchen, bathroom, three bedroom, wrap around porch and large garage area. The custom firepit w/ swings is the perfect place to spend the evening watching the stars and enjoying nature. This home boasts many amenities including disc golf, hiking trails, outdoor seating, foosball, ping pong table, corn hole boards and so much more. 3 camper hookups avail.

Fiddlewood Farm Barn Stay & Experience

Welcome to Fiddlewood Farm! Our cozy barn farm stay is a haven for nature lovers & tranquility seekers. Immerse yourself in breathtaking scenery, ideal for unwinding & enjoying a good book. Experience the essence of farm life by joining us for morning chores, & interacting with friendly animals. Indulge in adventure at our stocked lake, offering fishing, kayaking, ziplining, & beach relaxation. Also enjoy all of our animals! Escape hustle, & fully embrace the beauty of farm life at Fiddlewood.

The Bluegrass House

Welcome y'all! Serene hot tub, fenced-in back yard (2-dog limit, extra charge). Airport shuttle (separate fee). Nestled near parks, 3 miles from Edge Ice/Sports Arena. Immerse yourself in cultural richness at Bluegrass Music Hall of Fame and Owensboro Symphony Orchestra. Enjoy free summer outdoor entertainment on the Riverfront. Holiday World (30+min). Experience southern style with breakfast at Windy Hollow Biscuit House, & ribs, mutton or burgoo at Moonlight BBQ (visited by celebrities).

Bluegrass Getaway • Swim, Relax & Unwind

Welcome to **Bluegrass Getaway**, your perfect retreat for relaxation and connection. This cozy home has 2 bedrooms 1 bath and features a private pool with lounge chairs, a firepit for evening gatherings, and a beautiful, fully stocked kitchen for all your cooking needs. The warm, inviting décor creates a comfortable space to unwind and make memories. Perfect for families or small groups, this getaway combines charm and comfort for an unforgettable stay. ** Heated Pool- Closes October 17th**

Lakeside Cottage

Perfect for couples! Thoughtfully designed with a soothing, rustic chic asthetic. Enjoy the peace and quiet, the wildlife, beautiful views and gorgeous sunsets from the tree tops! Propane fire pit on deck & wood fire pit in the yard with wood provided. About a 15 min drive into Owensboro which is a very cool year-round Rivertown with plenty of restaurants, shops, pubs, and especially the beautiful Riverfront Park! We are also on the Bourbon Trail! Bring your kayaks and enjoy the lake!

The Woodford Retreat Cottage

Take it easy at this unique getaway.. Completely renovated 2,000 sq ft home with a beautiful river view, 3 bedrooms, 2 family rooms, 2 full bathrooms, fully stocked kitchen. The back yard is fenced with a deck, patio table and glider. This property is located a few blocks from the Owensboro Convention Center, Bluegrass museum, and multiple downtown restaurants. This property adjoins English park. Excellent rental for a weekend of downtown adventures or just enjoying the river view.

Rustic Log Cabin Old Farm

Step back in time at this 1800s log cabin on historic DeLacey Farm. Surrounded by barns, wildlife, and wide-open fields, this rustic getaway sits on a nearly 100-year-old working farm—just minutes from Owensboro’s BBQ, bourbon, and small-town charm. Relax on the back deck with views of the original farm buildings, or head into town to explore the Green River Distillery and local eats. It’s the perfect blend of peaceful retreat and convenient access to everything Owensboro has to offer.

The Blue Heron of Carpenters Lake

Welcome to your peaceful lakeside escape. This cozy home has two bedrooms that sleep up to 6 guests and 1 full bathroom, thoughtfully designed for relaxation and comfort. Wake up to amazing lake views, unwind by the water and enjoy endless activities year around from summer swims, hiking, kayaking, games in the garage, or evening relaxing on the patio. Whether you’re seeking adventure or quiet moments by the lake, this home is an ideal place to stay to slow down and recharge.

The Guest House at Kate & Waverly

Welcome to the Guesthouse at Kate & Waverly! This beautiful historic building, built in 1902, is located in downtown Owensboro. We are walking distance to many downtown restaurants and bars, as well as the Convention Center, Bluegrass Music Hall of Fame, Bluegrass Fieldhouse, and the beautiful Ohio riverfront and park. The AirBnB is located on the second floor above Kate & Waverly—a gift shop with unique vintage and antique finds, as well as an interior design center.

Midtown Cottage- Self Check-In & Centrally Located

Enjoy your stay in Owensboro, KY in this cozy, warmly decorated home! This home is centrally located to everything Owensboro has to offer, a short drive from downtown and the award winning riverfront. Wifi and parking are included. Enjoy a stylish experience at this centrally-located home. You will enjoy relaxing either in the home or the lovely backyard space. Whether you are in town for work or play indulge in the comfort and tranquility of this modern house.