Guesthouse vacation rentals in Kentucky

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Top-rated guesthouse rentals in Kentucky

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Top guest favorite

The exterior view showcases a modern cottage with a striking red front door and two large windows. A pathway leads up to the entrance, bordered by landscaped greenery and a potted plant on one side, enhancing the inviting appearance of the space.

Guesthouse in Lexington

4.98 out of 5 average rating, 129 reviews

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 A cozy backyard cottage nestled in historic Pensacola Park, part of the national register of historic places. Conveniently, located along Hwy 27 (Nicholasville Road). A stones throw from the University of Kentucky, Kroger Field, 3 hospitals (Baptist Health, UK, and Children's Hospital), and Lexington's celebrated state botanical garden: The Arboretum. This standalone cottage features one dedicated parking space, full amenities, garden views, and artistic embellishments.

Top guest favorite

A brick pathway leads to a charming cottage with a black front door and dark shutters. The cottage is framed by lush greenery, creating an inviting entrance. Sunlight filters through the trees, illuminating the pathway and surrounding landscape.

Guesthouse in Nicholasville

4.98 out of 5 average rating, 348 reviews

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.

Top guest favorite

The bathroom features a sleek black cabinet and a white sink with a matte black faucet. Four neatly rolled towels are mounted on the wall. A large mirror reflects the space, while air conditioning is visible above. Decorative wall baskets hold additional toiletries.

Guesthouse in Scottsville

4.98 out of 5 average rating, 218 reviews

Adorable Guesthouse #2 Close to Barren River Lake

We are excited to present our tiny guest home #2. Perfect for the fisherman or couple wanting to stay close to Barren River Lake or Mammoth Cave. This unit is centrally located between several towns and less that four miles from Port Oliver Boat Ramp and Dam. It is close to the main house so we will be available if you need anything. Peaceful surroundings, comfortable queen bed, refrigerator, microwave and coffee bar. 55" smart tv to kick back & relax with. Exterior outlet for boat.

Guest favorite

A charming exterior view of the house features a welcoming porch with decorative plants and an American flag. A concrete pathway leads from the sidewalk to the entrance, flanked by manicured lawn areas and mature trees providing shade.

Guesthouse in Winchester

4.93 out of 5 average rating, 199 reviews

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

Top guest favorite

A detailed map featuring prominent local attractions is displayed, highlighting their distances from the property. Icons indicate walking and driving times to destinations such as the Kentucky State Capitol and nearby distilleries, aiding guests in planning their visits.

Guesthouse in Frankfort

4.94 out of 5 average rating, 212 reviews

The Carriage - Quaint Haven steps to the Capitol

Escape to a charming retreat in Historic Frankfort, just minutes from 13 iconic distilleries. As the weather warms, enjoy a Parisian-inspired pied-à-terre that blends comfort and style. Skip the crowded hotels; relax with private access, free street parking, Wi-Fi, a smart TV, full kitchen, and the KY Capitol nearby. Cozy up in a plush queen bed, surrounded by warmth and charm. Enjoy the quiet deck with a bistro table; perfect for coffee or wine. Make lasting memories in every season.

Guest favorite

Two gray Adirondack chairs are positioned around a circular stone firepit, which features a glowing fire at its center. Surrounding the area are trees and lush greenery, providing a natural backdrop for outdoor relaxation.

Guesthouse in Lexington

4.91 out of 5 average rating, 261 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Top guest favorite

Soft morning light filters through trees onto a lush green lawn, creating a tranquil scene. A rustic well stands under a wooden pergola, complemented by a small bush nearby. The distant water's surface glimmers, enhancing the peaceful ambiance.

Guesthouse in Lancaster

4.99 out of 5 average rating, 206 reviews

Wishing Well Guesthouse On The Lake

A peaceful, waterfront guesthouse in a serene quiet neighborhood. On 2 acres of rolling hills, this choice location will be a peaceful getaway. Updated furnishings and appliances in this beautiful, open concept living space with a gas fireplace inside or a rustic fire pit outside. Close to lake marina rentals. #Center College #Pioneer Playhouse #Brass Band Festival #Pasture at Marksbury Farm #KY BBQ Festival #Bourbon Trail #Norton Center For The Arts #127 yard sale

Guest favorite

A well-defined pathway is illuminated by small lanterns, guiding guests toward the cottage nestled among trees. The gentle glow from the lights contrasts with the surrounding dusk, creating a serene approach to the inviting space.

Guesthouse in Shelbyville

4.97 out of 5 average rating, 112 reviews

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 that flows 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.

Guest favorite

A private outdoor space is presented with a hot tub and a fire pit surrounded by seating. Lush greenery provides privacy, while colorful flowers add a welcoming touch. A patterned rug is placed under the seating area, inviting relaxation in this tranquil setting.

Guesthouse in Lexington

4.94 out of 5 average rating, 523 reviews

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

Top guest favorite

A front garden displays vibrant orange flowers alongside lush green foliage. A yellow sign with red text is positioned among the blooms, while the steps leading to the entrance of the home are framed by stone edging. The entrance door is partially visible in the background.

Guesthouse in Louisville

4.96 out of 5 average rating, 232 reviews

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.

Top guest favorite

A welcoming countertop setup features a vibrant flower arrangement in a black vase, alongside a wood sign reading 'Welcome to Frankfort'. Nearby, a brochure and a plate of chocolates are thoughtfully arranged. A sheet of information is also presented, creating an inviting first impression.

Guesthouse in Frankfort

4.99 out of 5 average rating, 123 reviews

Treetop Hideaway

Fully equipped apartment, only 5 blocks from the state Capitol in historic, tree-lined neighborhood. Kentucky Derby, Horse Park, and Bourbon Trail all close. Real pricing - no hidden fees! Downtown restaurants, entertainment, & distilleries are only minutes away by car or foot. Apartment includes everything for short-term or extended stays, including washer/dryer and fully-equipped kitchen. Separate building - totally separate entrance for privacy.

Top guest favorite

A modern coffee maker in mint green is positioned on a dark countertop next to two decorative mugs. The coffee maker features a simple design with a water reservoir and a cup holder, while nearby, electrical outlets are visible.

Guesthouse in Leitchfield

5 out of 5 average rating, 106 reviews

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.