Holiday rentals in Whitesville

4.95 out of 5 average rating, 374 reviews

The charming front porch is visible, featuring two red rocking chairs and a welcoming American flag. Lush green bushes frame the path leading up to the entrance, while a well-maintained yard provides a spacious outdoor feel. A bright blue sky complements the inviting atmosphere.

Home in Beaver Dam

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. You are minutes from stores/ food.

5.0 out of 5 average rating, 41 reviews

A peaceful countryside scene features rolling hills and a clear pond surrounded by trees. Bare branches indicate the changing seasons, while a vibrant blue sky is dotted with soft clouds, creating a serene backdrop of nature.

Home in Olaton

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.

4.81 out of 5 average rating, 47 reviews

A hexagon structure is illuminated by string lights, featuring four swinging chairs arranged around a central fire pit. A stack of firewood is positioned nearby on a gravel surface, surrounded by trees that create a secluded outdoor atmosphere.

Barn in Philpot

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.

4.95 out of 5 average rating, 75 reviews

A peaceful scene on the farm shows a person interacting with sheep and pigs in a grassy area. The animals appear curious and friendly, surrounding the individual in a natural setting. The greenery of the grass provides a vibrant backdrop to the moment.

Barn in Philpot

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.

A spacious living area is furnished with a large sectional sofa, complemented by decorative pillows. A ceiling fan provides airflow, while natural light filters through the window blinds. A guitar hangs on the wall, and a wall-mounted artwork adds a pop of color.

4.9 out of 5 average rating, 136 reviews

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).

5.0 out of 5 average rating, 121 reviews

An outdoor fire pit area is surrounded by six wooden Adirondack chairs, creating a cozy gathering spot on a grassy lawn. The former church building is visible in the background, framed by trees and bathed in natural light.

Home in Grandview

The Storehouse - unique retreat near Holiday World

The Storehouse, a church built in the 1890s, is nestled in the serene backdrop of Grandview, Indiana. This former sanctuary has been thoughtfully transformed into a 3 BR home, perfectly blending old-world charm with contemporary amenities. You will love the original hardwood floors and stained glass windows in every room. Less than 15 min. from Holiday World and Lincoln State Park, there is much to do. Return and unwind in the private hot tub or gather around the fire pit under the stars.

An open concept living area features a plush gray sofa with accent pillows, complemented by a modern coffee table on a textured area rug. The kitchen area includes wooden cabinets and bar seating, while natural light brightens the space through a nearby window.

5.0 out of 5 average rating, 196 reviews

4bed3BR 35 to HolidayWorld/Near Conv Ctr/Fisher Pk

METICULOUSLY CLEAN, updated 3 bedroom home, 4 beds each with tv! Home is 3 miles from Convention Ctr, Bluegrass Museum, Science Museum, Botanical Garden. It’s also 4 minutes from baseball fields (Fischer), Thompson Berry( soccer), 35min to Holiday world, private and fenced backyard with lighted patio. Home is well stocked with ALL you may need! If the home is empty previous night, early check in, no charge! - Wifi - Roku TV in all bedrooms - Washer and Dryer - Stocked kitchen, book now!

4.98 out of 5 average rating, 176 reviews

The exterior of a renovated two-story home is featured, showcasing a distinct architectural design with exposed beams. Large windows allow natural light to enter, while a welcoming front door is framed by decorative lighting fixtures. A concrete pathway leads to the entrance.

Cottage in Owensboro

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.

A single-story home with a brick facade is presented. The driveway leads to a garage, while a well-maintained lawn features neatly trimmed grass and colorful flowerbeds. Large front windows allow for natural light, framed by light-colored siding underneath a gabled roof.

4.94 out of 5 average rating, 141 reviews

Bluegrass Commons

You will be close to everything when you stay at this centrally-located three bedroom two bath home right off the bypass that is a short drive to anywhere in Owensboro, KY for any business travelers. This is a brand new construction home in Bluegrass Commons neighborhood! New furnishings and the home sleeps 6 comfortably. Split bedroom with an open concept perfect for families. Fully stocked kitchen with a keurig coffee station. Large backyard perfect for entertaining or just grilling.

A charming exterior of a gray house is framed by neatly trimmed hedges and a manicured lawn. A short concrete path leads to the front door, which features decorative details. A small orange awning adds a pop of color above the front window, set against a bright blue sky.

4.88 out of 5 average rating, 117 reviews

Hill Ave home

Make some memories at this uniquely remodeled home with 3bdrms and 1 bath with 1 bath outside thats seasonal We have a high chair! Ping pong table and multi game table upstairs! Kitchen, dining rm, and living room are open concept. There is a den with a tv as well as living room tv. 1bdrm has office desk. It has a large deck with a gas stove and grill as well as patio table! Its fenced in for privacy! Basketball, swimming, and fitness center across the street! You will enjoy!

5.0 out of 5 average rating, 28 reviews

Flat in Owensboro

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.

A spacious living area features a large flat-screen television mounted on a dark wall. Two light gray sofas are arranged around a round coffee table on a textured rug. Soft lighting from two side tables complements the warm wooden flooring.