Holiday rentals in Whitesville

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Top-rated holiday rentals in Whitesville

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Top guest favourite
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. Food and shopping all minutes away

4.95 out of 5 average rating, 375 reviews
Top guest favourite
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.

5.0 out of 5 average rating, 42 reviews
Guest favourite
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.

4.81 out of 5 average rating, 47 reviews
Guest favourite
A spacious living area is highlighted by a decorative fireplace with a round mirror above it. A modern ceiling fan hangs overhead, while a glass coffee table sits on an area rug. A compact desk and television unit are also visible, contributing to a warm atmosphere.
Home in Owensboro

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**

4.85 out of 5 average rating, 61 reviews
Top guest favourite
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.

4.98 out of 5 average rating, 178 reviews
Top guest favourite
A rustic log cabin is set against a backdrop of greenery, with a large Osage Orange tree providing shade. The cabin features a combination of natural wood exteriors and a modern addition, showcasing a warm and inviting entrance surrounded by well-maintained landscaping.
Cabin in Utica

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.

5.0 out of 5 average rating, 46 reviews
Guest favourite
Home in Maceo

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.

5.0 out of 5 average rating, 22 reviews
Top guest favourite
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.

5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Owensboro

The Cozy Cottage

Join us for a relaxing stay at the Cozy Cottage! Inside you will find everything you need to make for a cozy stay whether you’re with us for short weekend or a month. Outside you will find plenty of spaces to sit and enjoy the view of the Ohio River just 2 blocks away. The Cozy Cottage is conveniently located less than 5 minutes from downtown Owensboro and popular attractions such as the Convention Center, Bluegrass Museum, Botanical Gardens, and Jack C. Fisher Park.

4.94 out of 5 average rating, 231 reviews
Top guest favourite
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.
Home in Owensboro

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.

5.0 out of 5 average rating, 201 reviews
Top guest favourite
Cottage in Owensboro

Nature Lovers Retreat

This charming cottage is the perfect getaway for nature lovers. Relax in this home’s cheerful and cozy atmosphere, located on the edge of Ben Hawes Park with over 4 miles of beautiful walking trails and 7.5 miles of bike trails in this gorgeous 297 acre forest. Enjoy all the comforts of home, including free WiFi, TV, washer and dryer, full kitchen, and free parking. This special retreat is also only 1 mile from Ben Hawes Golf Course.

4.97 out of 5 average rating, 437 reviews
Superhost
A spacious kitchen features wooden cabinets and a granite countertop island. Four wooden dining chairs surround a rectangular table. A door leads outside, and natural light enters through two windows dressed with light curtains.
Holiday home in Owensboro

The little big cozy house

The little big cozy house offers you a place where you can relax and feel at home. a spacious kitchen with all the necessary elements such as The 3 bedrooms ,that invite you to rest with very suitable beds For you to spend a magnificent and comfortable night. The patio is a space where you can enjoy a grill surrounded by family or friends. This house is an excellent location that gives you quick access to any part of owensboro.

4.88 out of 5 average rating, 164 reviews

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