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.

Williamsburg Poolside Homestead

Private guest house with incredible outdoor resort feel, nature, and simple homestead life. 3 miles to University of the Cumberlands. 20 min to Cumberland Falls, home of the world's only Moonbow. *NO smoking of any kind (e-cig included) permitted anywhere on the property or the entire neighborhood. Guests violating our smoking policy are subject to a minimum $400 fee for returning the house or property to smoke-free status and agree to being charged by accepting this policy.

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.

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.

HIghlands Modern Get Away

Ideal, quiet place in the highlands. You have the apartment over the garage. You'll have a place all to yourself with most the amenities of your own home. Studio apartment with a balcony if you decide to hang out and relax for the evening. There is a cook top, but no oven in the kitchen. Park in the driveway in front of the garage. Pets are welcome, plz add them when booking.

Tiny Tailor House

1888 Tailor Shop, converted to a cozy "Tiny Tailor House", in historic Mutter Gottes neighborhood. One block from MainStrasse Village. Short walk to dining, sporting events, entertainment, shopping, and convention centers, on both sides of the Ohio River.