Vacation rentals in Drakesboro

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Top-rated vacation rentals in Drakesboro

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Top guest favorite

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

4.95 out of 5 average rating, 326 reviews

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.

Top guest favorite

A charming treehouse design is perched above the forest floor, featuring large windows that invite natural light. A spacious deck with a railing extends from the structure, and wooden stairs lead down to a gravel area with stacked firewood nearby. The surrounding trees create a secluded setting.

Treehouse in Franklin

4.99 out of 5 average rating, 108 reviews

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

Top guest favorite

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

4.97 out of 5 average rating, 151 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. 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.

Guest favorite

A cabin with a rustic wooden exterior features a welcoming wrap-around porch supported by sturdy posts. Large windows invite natural light, and a balcony extends from the upper level. Surrounding greenery offers a peaceful setting, enhancing the cabin’s connection to nature.

Cabin in Lewisburg

4.96 out of 5 average rating, 164 reviews

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!

Top guest favorite

The exterior of a rustic cabin features a combination of log siding and a green metal roof. A spacious covered porch welcomes guests, with large columns supporting the overhang. Surrounding trees provide shade and natural beauty, enhancing the serene rural setting.

Cabin in Russellville

4.96 out of 5 average rating, 135 reviews

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.

Top guest favorite

The treehouse is illuminated by soft outdoor lights, highlighting its wooden structure and welcoming design. A gently curving walkway leads to the entrance, surrounded by tall trees and a glimpse of Lake Malone visible in the background.

Treehouse in Lewisburg

4.97 out of 5 average rating, 112 reviews

Aerial Joy Treehouse(Lake Malone)

Prepare to be taken to new heights as you enjoy this beautiful, private treehouse located on Lake Malone. It features an absolutely stunning view of the lake through an 8x14 glass door that opens up to allow the cool lake breezes to waft your cares away as you relax in the recliner. It also features a large deck, full kitchen, Jacuzzi tub, rainfall shower, beautiful woodwork, two complimentary kayaks, and many other unique features that will make your stay unforgettable.

Guest favorite

The entrance to the cabin is framed by wooden siding, featuring a central door adorned with a seasonal wreath. Natural elements, including pumpkins, are arranged on a small porch flanked by rustic decorations and a wooden fence made of branches.

Cabin in Dixon

4.9 out of 5 average rating, 509 reviews

Handcrafted Cabin in Woodsy Heaven

PLEASE read listing before booking. 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.

Top guest favorite

Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.

Cabin in Russellville

4.99 out of 5 average rating, 134 reviews

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). 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!

Superhost

The exterior of the house features a multi-level structure with wooden decks surrounded by green foliage. Steps lead up to the main entry, where lighting fixtures illuminate the space. A screened-in porch is visible on the upper level, providing access to outdoor relaxation.

Home in Lewisburg

4.93 out of 5 average rating, 144 reviews

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!

Top guest favorite

The kitchen features a U-shaped countertop with wooden cabinetry and a deep sink, complemented by a tile backsplash. A dining area with a round table and chairs is visible in the background, along with a decorative wall piece and clock adding subtle detail to the space.

Farm stay in Hopkinsville

4.84 out of 5 average rating, 129 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.

Top guest favorite

A spacious bedroom features large glass doors, offering views of the surrounding nature. Soft natural light fills the room, highlighting a comfortable queen bed with crisp linens. Nearby, a cozy seating area and a small workspace complement the inviting atmosphere.

Tiny home in Hopkinsville

5 out of 5 average rating, 133 reviews

Romantic, Peaceful Getaway in Nature

Enjoy beautiful views of nature when you stay in this unique place! Large windows on two sides of the home make it a truly serene space. Whether you are looking to walk trails on the property or enjoy the scenery in the comfort of home, you will find serenity during your stay here. If you'd like to bring a well-behaved dog, check out our other very similar rental! www.airbnb.com/h/3907witty

Guest favorite

The two-story home, identified as River Trails Inn, features a welcoming facade with a front porch and American flag. Lush green grass surrounds the property, and a clear blue sky provides a serene backdrop. Well-maintained landscaping enhances the inviting appearance of the entrance.

Home in Livermore

4.97 out of 5 average rating, 116 reviews

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!!