Guest house holiday rentals in Kentucky

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.

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.

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.

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.

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

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.

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.

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.

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.