Guesthouse holiday rentals in Kentucky

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Top-rated Guesthouses in Kentucky

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

An indoor heated pool is enclosed within a greenhouse, surrounded by lush greenery and potted plants. The water appears inviting and clear, reflecting the natural light filtering through the translucent roof. Decorative elements, including sculptures, enhance the tranquil atmosphere.

Guesthouse in Dayton

Art Studio at Turtle Hill, 5-Acre Oasis Near City

The Art Studio at Turtle Hill is located in Dayton, Ky, 2.2 miles from downtown Cincinnati. The studio is situated on 5 acres overlooking the Ohio River. The main house has a heated enclosed pool that is available to guests, a fire pit and pond. The studio has a full laundry, full kitchen and 4 off-street parking spots. The main bedroom (one queen) is on the first floor and the second bedroom (2 twins) is a loft. No cleaning fee. The studio is not suitable for children under 12. No pets please.

LocationValueHot tub

4.97 out of 5 average rating, 250 reviews

Top Guest favourite

A charming red garage structure is presented under a bright blue sky with fluffy clouds. The building features a distinct sloped roof and balconies above the entryway, flanked by trees that reflect the serenity of the surrounding forested area.

Guesthouse in Stanton

Forest Edge Retreat; Cozy Charm w Hottub Wi-Fi

Giving treehouse vibes, my cozy retreat sits at the base of a forested mountain w 50 acres of wooded mountainside to explore here or a short 15 min drive to RRG. This cozy private space is the upstairs level of my storage garage which is next door to my farmhouse rental. The farmhouse & Retreat each have their own separate private driveway. We're in a peaceful rural neighborhood only 5 mins to Stanton or 15 mins to Red River Gorge. Garage parking not included, but plenty of driveway space.

FamilyValueParks

5.0 out of 5 average rating, 104 reviews

Top Guest favourite

Lush green grass frames the scene, with two flowering trees prominently in the foreground. A wooden fence lines the area, leading to a cottage that is partially obscured by the trees. Natural light brightens the surroundings on a clear day.

Guesthouse in Nicholasville

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

ValueFamilyHiking

4.98 out of 5 average rating, 397 reviews

Top Guest favourite

An outdoor gathering space is highlighted, featuring a circular structure with a metal façade. Strings of lights create a warm ambiance against the dusk sky. A large flat-screen television is mounted on the wall, complementing the open seating area with various tables and chairs.

Guesthouse in Springfield

Lofty Lodge on the Bourbon Trail

Come to the Bourbon Trail in the Heart of Kentucky! Stay at our beautiful lodge with large common areas perfect for hanging out! Our space is great for family trips, work retreats, or a couples get away! The lodge is located just 3 miles from from restaurants, groceries, pharmacies and shops. But at the Lodge you will enjoy the peace of the country. We are central to all the bourbon distilleries: 15mi to Maker's mark, 35mi to Jim Beam, 50mi to Woodford Reserve, Lexington and Louisville.

FamilyLocationParking

4.99 out of 5 average rating, 138 reviews

Top Guest favourite

Guesthouse in Stanton

Robbie’s Rest: Amazing Mountaintop Sunrises

2020 new unit with nice deck, wonderful mountain scape with amazing sunrises from your deck or the deck of the main house where host lives. 8 acres that sit where the rolling hills meet the mountains overlooking the Daniel Boone Forest. 35 miles from Lexington, you will enjoy the peace & quiet of the beautiful mountains. Minutes away from the trails, waterfalls & attractions of Natural Bridge State Park & the Red River Gorge! We hope you will visit us soon! *Sunrise is not always visible

FamilyLocationAir conditioning

4.98 out of 5 average rating, 376 reviews

Top Guest favourite

A cozy sleeping area features a spacious bed with crisp white linens. An inviting sitting area with a white couch rests next to a wooden wardrobe. Natural light filters through nearby windows, highlighting the room's soothing decor and warm atmosphere.

Guesthouse in Frankfort

The Carriage - Quaint Haven steps to the Capitol

Your perfect Kentucky getaway starts here. Tucked in Historic Frankfort, this charming Parisian-inspired retreat is minutes from 13 renowned bourbon distilleries, the Kentucky Capitol, and downtown favorites. Spend your days tasting, exploring, and discovering local history, then unwind with a glass of your perfect drink on your private bistro deck. Thoughtfully designed for comfort and relaxation, this cozy hideaway is the ideal home base for an unforgettable Bourbon Country escape.

FamilyValueGetting around

4.94 out of 5 average rating, 266 reviews

Top Guest favourite

The spacious living area features large, historic arched windows that allow natural light to fill the room. A comfortable blue sofa is positioned near a circular dining table, complemented by a modern ceiling light fixture and a flat-screen television mounted on the wall.

Guesthouse in East Market District

Lavish church suite with choir loft

Indulge yourself with soaring ceilings, chef's kitchen, luxurious king bed, and soaking tub, all in a landmark church surrounded by Louisville's hottest neighborhood, NULU. Our grandest renovation at the Holy Goat, The Revival Loft, lets you gaze through large, historic church windows while sipping your morning coffee or evening bourbon. Built in 1843 this former church is now home to one of Louisville's most unique guest houses, steps from the city's best food, drink, and culture.

LocationValueAccuracy

4.99 out of 5 average rating, 104 reviews

Guest favourite

The charming cottage is set against a backdrop of lush greenery, featuring a welcoming front porch with two chairs. The exterior showcases light grey siding complemented by red shutters and door, while a clear driveway leads to the entrance.

Guesthouse in Cecilia

Cottage at the Hundred Acre Wood

Escape to the country and take it easy at this unique and tranquil getaway. This beautiful cottage shares the yard and scenery with the owner’s residence, but is a very peaceful & nice space to relax and sleep at the end of your day. You’ll be out in the country but still conveniently located, only about 15 min from everything. 16 minutes from Glendale - Ford Blue Oval plant 14 minutes from Etown Sports Park 16 minutes from downtown Etown & all the great restaurants and stores

FamilyValueCheck-in

4.93 out of 5 average rating, 128 reviews

Top Guest favourite

A spacious bedroom features a large bed with dark bedding centered on wooden floors. Two cozy armchairs are positioned nearby, complemented by a vibrant area rug. A decorative mirror and framed artworks adorn the walls, while a bookshelf holds an array of books, adding character to the space.

Guesthouse in Louisville

Comfortable-relaxed space to find your inspiration

Located in the Germantown neighborhood of Louisville, this peaceful efficiency apartment in a traditional "shotgun" home, built in the 1890s, is within 10 minutes of nearly all of Louisville’s airport traveler’s attractions. Guests enjoy great sleep on top bedding and attention to detail. Sit on the front porch and let time slip by or spend the evening with a relaxing drink or meal in one of the neighborhood’s hip local eateries and bars. Plan your next journey.

ValueLocationLong stay

4.96 out of 5 average rating, 245 reviews

Top Guest favourite

A comfortable living area features a neutral-colored sofa and a wooden coffee table. A ceiling fan hangs above, while a television is mounted on the wall above a decorative fireplace. Natural light enters through two windows, complemented by rustic wall accents.

Guesthouse in Shelbyville

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Listen to the birds sing as the walkway guides you to your quaint cottage getaway. Take in nature, as you’re surrounded by trees, near our sweet chicken coop and a creek down from the deck - all while only 10min from town. Special touches were added of Kentucky Derby photos, books, kitchenware, Bourbon Trail glasses and bourbon barrel heads with local distilleries. The dining table top is even made of wood from Shelby County’s own Bulleit Distilling Company.

ValueLocationView

4.97 out of 5 average rating, 146 reviews

Top Guest favourite

A television is positioned on a dark wooden stand beneath a decorative sign that reads 'FAMILY.' A potted plant adds a touch of greenery on the stand. Light-colored walls and a door with a window create a welcoming atmosphere.

Guesthouse in Leitchfield

The Treehouse

Keep it simple at this peaceful and centrally-located 2 bedroom, 1 bath second floor apartment. Fully furnished, cozy, and located right in the center of Leitchfield. Also centrally located between Rough River (10 minutes) and Nolin lake (22 minutes) with room for boat trailer parking. With restaurants and grocery stores less than 5 minutes away, this apartment is also perfect for extended stays. Both bedrooms are furnished with queen beds.

FamilyLocationOutdoor spaces

4.99 out of 5 average rating, 182 reviews

Top Guest favourite

A spacious entryway features a striking artwork installation on the black wall, complemented by a spiral staircase leading to the upper level. Comfortable seating includes a tufted leather chair and a plush sofa, with a round wooden coffee table at the center on a decorative area rug.

Guesthouse in Somerset

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

FamilyLocationNearby

4.98 out of 5 average rating, 233 reviews