Holiday houses in Whitesville

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Top-rated holiday rentals in Whitesville

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The cottage features a welcoming front porch adorned with red shutters and a bright red door. Two large, round rocking chairs are positioned on the porch, surrounded by greenery and a blue planter. The pathway leads to the spacious entrance.
Cottage in Maceo
4.96 out of 5 average rating, 182 reviews

Hattie's Hill Cottage

Cozy cottage located just behind the main home on the property (see photos). Relax by the pool, open seasonally, which is shared by the main house guests and host family, or enjoy an evening stroll out in the country. Conveniently located near Owensboro, Rockport, Hawesville, and Lewisport. The cottage features one flexible bedroom with either two twins or one California king, Wi-Fi, Smart TV, well-stocked kitchen, dining/work space, comfortable recliners, and access to the beautiful grounds.

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
4.8 out of 5 average rating, 45 reviews

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.

Guest favourite
A charming log cabin is illuminated at night, showcasing warm lighting that highlights its rustic architecture. A front porch extends along the cabin, providing a welcoming entrance. Surrounding grass features a natural landscape, enhancing the cabin's peaceful setting.
Cabin in Falls of Rough
4.91 out of 5 average rating, 32 reviews

Geno and Rocco's at Rough River, Lake Front Cabin

Escape to this cozy 2-bedroom, 1-bath cabin at Rough River Lake! Sleeping 6 with 3 beds, it overlooks the river banks and offers a fire pit area, picnic table, and a front porch with rocking chairs. The kitchen is fully stocked with all new pots, pans, dishes, and a coffee maker. Enjoy the provided indoor/outdoor games, bikes, books, fishing, kayaking, and a nearby golf course. Smart TV'S and high-speed WiFi for streaming available. Need something else? —just ask! As always pets are welcome.

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
5 out of 5 average rating, 32 reviews

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.

Guest favourite
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.
Home in Owensboro
4.93 out of 5 average rating, 137 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.

Top Guest favourite
Home in Owensboro
5 out of 5 average rating, 68 reviews

Village Cottage - 1 King+1 Queen | 2 Baths | Patio

Welcome to your home away from home at The Village Cottage! While you’ll feel tucked away in a peaceful, family-friendly neighborhood, this cozy 2-bed, 2-bath home offers the perfect retreat for anyone visiting Owensboro. Within just a few minutes, you can reach the convention centre, downtown, hospital, grocery stores, cafes, restaurants, movie theatre, casino and the green belt. Whether you're in town visiting family & friends or on a business trip, we look forward to hosting you!

Top Guest favourite
A cozy living area features a plaid couch positioned next to an ottoman and a small side table. A wooden bench sits against the wall under a mirror. A television is mounted on the wall opposite the entrance door, with natural light illuminating the space.
Apartment in Hawesville
4.97 out of 5 average rating, 91 reviews

Highlander's Hidden Gem 1 Bedrm

Drive right up to your front door! There is only one other apartment sharing this location. Amenities include wifi, smart televisions in living room and bedroom, couch that folds out into a full size bed (pillows and blankets are in the ottoman in front of couch), eat in kitchen, and free parking. Even though this is a small town, there is a convenience store 1/2 block away, a Walmart that is 3 and 1/2 miles away, and two other local restaurants that deliver to your door.

Top Guest favourite
A deck area is presented with a dining table covered by an umbrella, surrounded by chairs. Soft lighting from candles creates a warm atmosphere, while lush trees provide a natural backdrop along the lakeside. The railing allows for unobstructed views of the serene environment.
Cabin in Maceo
4.99 out of 5 average rating, 81 reviews

Lakeside Cottage

Perfect for couples, a private getaway with a soothing, rustic chic asthetic. Enjoy 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. Lots of places to relax around the property. About a 15 min drive into Owensboro which is a very cool year-round Rivertown! Be sure to check out Friday after 5:00 if you're coming on a Friday! Let us know if you are bringing kayaks or canoes please!

Guest favourite
The exterior of the Cozy Cottage is presented, showcasing a two-story structure with blue shutters and flower boxes. A set of wooden stairs leads to the entrance, which is framed by a tree that provides shade. The surrounding yard features green grass and a pathway.
Home in Owensboro
4.94 out of 5 average rating, 217 reviews

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.

Top Guest favourite
Cottage in Owensboro
4.97 out of 5 average rating, 428 reviews

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.

Guest favourite
A spacious living area is highlighted by a large sectional sofa adorned with decorative cushions. A flat-screen TV is mounted on the wall, while a ceiling fan provides airflow. Natural light enters through an open doorway leading to a dining space, enhancing the inviting ambiance.
Apartment in Owensboro
5 out of 5 average rating, 11 reviews

Bluegrass Hideaway

Cozy 2-bedroom, 1-bath retreat perfect for families, friends, or business travelers. Sleeps 4 comfortably with plush bedding. Fully equipped kitchen, spacious living area, high-speed WiFi, and Smart TV for entertainment. Fresh towels and toiletries provided. Free parking available. Conveniently located near restaurants, shopping, and local attractions. Experience comfort and convenience in a relaxing space. Book your stay today!

Guest favourite
A sliding door opens onto a spacious deck, framed by a wrought iron screen. Outdoor seating is positioned on the deck, facing a green yard and trees, allowing for a serene view of nature.
Loft in Hartford
4.96 out of 5 average rating, 181 reviews

Cozy One Bedroom Apartment in the Country

What was originally a hay loft has been converted into a country chic barn apartment. We would love to host you and your friends and family (including actual kids and fur kids) on our property. We are only an hour from Mammoth Cave National Park and an hour from Holiday World in Santa Claus Indiana. The local community has charming little shops, several restaurants, and The Beaver Dam amphitheater.

Popular amenities for Whitesville holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Daviess County
  5. Whitesville