Vacation rentals in Drakesboro

4.95 out of 5 average rating, 310 reviews

A charming house is seen from the side, featuring a carport that shelters a vehicle. The property displays a well-maintained yard with green grass and blooming flower bushes. A gravel driveway leads to the corner lot, surrounded by trees providing a lush backdrop.

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.

4.93 out of 5 average rating, 14 reviews

The cozy interior features warm wooden walls and ceiling, creating a welcoming ambiance. A red retro refrigerator stands out against the neutral-toned cabinetry, accompanied by a microwave. A comfortable brown sofa invites relaxation, adorned with a decorative pillow that reads, 'LOVE YOU MORE.'

Tiny home in Beaver Dam

A Cozy Kentucky Retreat

Nestled in the serene countryside, our cozy tiny home offers the perfect escape just minutes from town. Enjoy the tranquility of nature while casting a line into the peaceful pond, complete with complimentary fishing poles for your convenience. Unwind by the campfire under the stars, sharing stories and savoring the warmth of the flames. This charming retreat is ideal for those seeking a blend of comfort and adventure, making it the perfect getaway in the heart of Kentucky’s beautiful landscape.

4.99 out of 5 average rating, 114 reviews

Cabin in Russellville

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). Just one hour from Mammoth Cave and Nashville! We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

4.97 out of 5 average rating, 139 reviews

A set of wooden stairs leads up alongside a red metal building, framed by a railing with a wire mesh design. The stairs, slightly worn, are surrounded by greenery, providing access to the upper level of the barn apartment.

Loft in Hartford

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. Children love collecting eggs from the chicken coop and everyone loves a short hike to the creek. 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.

4.96 out of 5 average rating, 160 reviews

A cabin with a wooden exterior and a metal roof is surrounded by lush greenery. A spacious wrap-around porch features wooden rocking chairs and a picnic table, while a deck above allows for additional outdoor seating. The gravel driveway leads to a grassy yard.

Cabin in Lewisburg

White Bluff Cabin with RV hookup on Lake Malone

White Bluff Cabin sits in a quiet,friendly neighborhood overlooking Lake Malone. It is privately owned and offers all the accommodations to make your stay a relaxing one. It is fully furnished. FREE WIFI and parking. There is also a RV hookup available to cabin guests only for an additional fee. Just a short hike down to the boat dock and you will see the white bluff to your left which the cabin sets on. Or simply rock away on the spacious wrap-around porch, sipping coffee or iced sweet tea!

4.95 out of 5 average rating, 118 reviews

The rustic cabin features a wooden porch supported by sturdy posts, inviting seating on one side. The structure displays a combination of log and modern siding, topped with a green metal roof. Lush greenery surrounds the cabin, offering a serene rural setting.

Cabin in Russellville

Cozy Cabin with Private Walking Trail

Relax and retreat to this peaceful rural cabin with modern amenities and charming outdoor spaces situated on a working farm. Enjoy the walking trail through 10 acres of woods or swing while enjoying beautiful country views. Experience the best of both worlds in the historic 19th century cabin with a modern addition. A short drive to quaint downtown Russellville, Auburn, or Franklin KY each with plenty of shopping. The nearby Red River provides opportunities for kayaking, tubing or fishing.

4.94 out of 5 average rating, 137 reviews

A wooden pathway bordered by lights leads to a gathering area with four chairs around a fire pit. Lush greenery surrounds the space, providing a serene atmosphere, while glimpses of the lake can be seen in the distance.

Home in Lewisburg

Laid Back Lake House w/ hot tub and private dock❗️

Come enjoy lake life in this newly renovated home located directly on Lake Malone! With relaxation and fun in mind you will have no problem finding something that entices everyone. From fishing and kayaking to relaxing in the hot tub we have you covered. Enjoy beautiful views that are sure to clear your mind and put you at peace from any of our decks. Pack up your family or friends and head to The Laid Back Lake house to start making memories!

Farm stay in Hopkinsville

An expansive field of blossoming fruit trees is set against a clear blue sky. The trees feature delicate white blossoms, with a lush green grass covering the ground. The scene conveys a sense of openness and tranquility within a natural environment.

4.83 out of 5 average rating, 120 reviews

Quiet country setting.

Hello! Thank you for considering staying with us during your stay in or around Hopkinsville, Ky. Whether you’re coming for work, pleasure or, to visit family, we think you’ll love staying here. It’s a warm and inviting home, with all the amenities you need for the perfect stay. We live on the farm, and will be around if you require anything during your stay. Please email if you have any questions. We look forward to hearing from you.

4.9 out of 5 average rating, 496 reviews

An outdoor porch is illuminated by warm string lights, creating a cozy setting. Comfortable seating is arranged around a table, surrounded by wooden railings. The natural backdrop features tall trees, enhancing the serene atmosphere of the space.

Cabin in Dixon

Handcrafted Cabin in Woodsy Heaven

Custom built wood cabin nestled in the rolling hills of western Kentucky. Cozy decor with vintage theme, handcrafted wood floors, and outdoor space overlooking wooded property. Rustic studio space full of modern amenities. Close proximity to 5450 acre Wildlife Management Area with hiking, horseback riding, fishing, hunting, and swimming. Perfect location to get back to nature. Great peaceful weekend or overnight getaway.

4.9 out of 5 average rating, 30 reviews

A hallway featuring two sliding barn doors on either side leads to a laundry area. The space contains modern, stacked washer and dryer appliances. Light-colored walls and wooden flooring contribute to a clean and functional environment.

Home in Bremen

The Tumbling K

This lovely farmhouse is the perfect place for a weekend getaway or a business trip. Wake up to beautiful blue skies and the birds singing. If you need to stay connected, Wi-Fi is available. If you want to disconnect, you can enjoy a book with your favorite cup of coffee in a quiet setting. Perfectly located between Madisonville, KY & Central City, KY. 62 miles from Evansville, IN 97 miles from Nashville, TN

4.97 out of 5 average rating, 109 reviews

A serene view of a river stretches out under a colorful sky, reflecting the greenery along the banks. A bridge spans the water in the distance, framed by trees showing hints of seasonal color. The riverbank is lined with grass and natural rock formations.

Home in Livermore

River Trails Inn

Historic two story home with three bedrooms and 3 1/2 baths, circa 1900, located in the old downtown district of the quaint river town of Livermore, Kentucky, just two blocks from the confluence of the Green and Rough Rivers and our expansive riverfront recreation complex. River kayaking and canoeing and biking trails on marked low-use county roads are right in your back yard!!

4.94 out of 5 average rating, 249 reviews

A wooden bridge leads from a grassy area towards a scenic view of open fields and trees in the distance. The soft morning light casts a gentle glow over the landscape, highlighting the natural beauty of the surroundings. The edges are bordered by a simple wooden fence.

Cabin in Hopkinsville

1 Bedroom, 1 Bathroom Cozy Cabin with Hot Tub.

The Lodge is a small 2 person only cabin on 45 acres of western KY countryside with amazing sunsets included. It has a private drive and a relaxing front porch with a 2 person only hot tub. Once you walk through the cabin doors, you will be transported to the Smokey mountains without the mountains. The owners live onsite if any problems arise that need immediate attention.

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Popular amenities for Drakesboro vacation rentals

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Other great vacation rentals in Drakesboro

4.87 out of 5 average rating, 134 reviews

A lit hot tub is positioned on a wooden deck, showcasing soft purple illumination. The surrounding area is dimly lit, creating a calm ambiance. A window reveals the structure's interior, enhancing the inviting atmosphere of the outdoor space.

Cabin in Falls of Rough

Waterfront Cabin with Hot Tub

BaileyRating, 5 stars2 weeks ago

We loved this cabin!! Perfect for a little getaway time. I couldn't make any phone calls due to zero service. But I was able to text via the Wi-Fi that is available. I had no problem with this, as I wanted to be off-grid as much as possible! The cabin has that nice "woody" smell immediately upon entering. The hot tub was ready to go when we arrived and was awesome! The neighboring cabins didn't bother us at all. We forgot they were even there. Everything we needed was provided. (Besides groceries, obviously!) I highly recommend this place if you're looking for some peace and quiet. It was so relaxing and gave me the recharge I desperately needed! It is the perfect spot for some tranquility. Thanks again, James!!!!

Farm stay in Bowling Green

4.91 out of 5 average rating, 395 reviews

Mammoth Cave/Beech Bend/NCM

MichaelRating, 5 stars3 weeks ago

Nice place. Note that all sleeping is upstairs. Older people I was traveling with did not appreciate this but it is in the listing. The place is very clean. Very nice setting. Very quiet and peaceful. There could be more amenities such as coffee and soap for the shower. Not a lot there so be sure to supply your own. I would stay again.

4.96 out of 5 average rating, 179 reviews

A spacious wooden deck is visible, featuring a corn hole board with bags organized nearby. Lush greenery is seen in the background, complementing the natural setting. The design of the deck is relaxed, inviting outdoor activities in a serene environment.

Cabin in Cub Run

Mammoth Cave - Nolin Lake

ColleenRating, 5 stars3 weeks ago

We stayed for the weekend to visit mammoth cave and dinosaur world! Kevin’s cabin provided all that we needed. Beautiful views, peaceful surroundings, and plenty of amenities. We cooked all meals at the house and had all the tools we needed.

4.81 out of 5 average rating, 109 reviews

The exterior of a two-story condo is depicted, featuring a mix of beige and brown siding. The entrance includes a covered porch with two doors. Symmetrical windows are positioned on both levels, allowing for ample natural light, while neatly trimmed shrubs line the front.

Condo in Clarksville

Charming Condo in Governors Crossing!

David AllenRating, 5 stars2 months ago

Loved my stay. I would recommend staying here. Felt at home and stay was comfortable. When I come back I plan on staying here again. Thank you for my time there.

4.92 out of 5 average rating, 112 reviews

A modern treehouse is elevated on wooden stilts, surrounded by lush greenery. Large windows allow natural light to fill the interior, and a wooden staircase leads to the entrance. The gravel path is lined with trees, emphasizing the tranquil forest setting.

Treehouse in Brownsville

The Birdhouse Tree house

HaleyRating, 5 stars4 days ago

Great spot for a family or a couple getaway. A little closer to the other two rentals on the property than I imagined they would be, but still very peaceful and we loved the firepit area. The creek is a great spot for kids to play and the covered patio was a nice addition to drink coffee or play a game during the rain. Nice touch providing games to play as the WiFi was a little slow and glitchy watching movies. Overall, loved the location- super close to Mammoth Park.

4.89 out of 5 average rating, 168 reviews

The interior of the cabin features warm wood paneling and a spacious living area with comfortable seating. A plush area rug covers the floor, and large windows allow natural light to fill the space. A staircase made of rustic wood leads to the upper level.

Cabin in Leitchfield

Rough River Lake Vacation Rentals hot tub WIFI

HeatherRating, 5 stars5 months ago

Our stay was perfection! If you are looking for a home with incredible attention to detail, private, and peaceful - this is it!

4.97 out of 5 average rating, 139 reviews

A modern kitchen is highlighted by dark cabinetry and stainless steel appliances. A wooden island with a woven basket can be seen in the center. Natural light filters through a window above the farmhouse sink, illuminating the tiled backsplash and wooden flooring.

Cottage in Owensboro

The Woodford Retreat Cottage

DavidRating, 5 stars4 weeks ago

wonderful stay. we were in Owensboro for 4 days. Had 3 couples in the house. Had a vintage show car that we got to keep and work on in the detached garage. Since it rained nearly everyday, this was a blessing. Great comfortable house..