Guesthouse vacation rentals in Lexington

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.

Value · Family · TV

Modern & Luxurious Carriage House on Paris Pike

This modern & luxurious 1 Bedroom, 1 Bath private carriage house is a dream! (Sleeps 3) The open ambiance, high ceilings, natural lighting & elegant features provide you with the vacation magic you desire. Come here to relax & enjoy all the charm Central KY has to offer. Surrounded by horse farms, the Carriage House at Warsaw is only minutes from the interstate, Horse Park, Lexington Country Club, Keeneland, Fasig-Tipton, downtown, UK, Red Mile, dining, shopping & more! License 15081686.

Value · Location · Getting around

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.

Value · Family · View

West meets South in this Garden Cottage Retreat

STR PERMIT #15078463 Guests must be 25+ in age. A cozy backyard cottage nestled in historic Pensacola Park. 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.

Family · Value · Comfort

My Old Kentucky Home-Downtown LEX's Premier Stay!

Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

Location · Family · Accuracy

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

Location · Value · Hiking

Carriage House Gardenside

Privacy and Convenience are yours when you stay at the Carriage House Gardenside. Located in historic Winchester, Carriage House Gardenside offers easy access to Lexington, the Kentucky Horse Park, Keeneland Race Course, the Bourbon Trail and Red River Gorge. Situated across from College Park and steps away from Winchester's public gym (indoor swimming pool and fitness center). Space features a king sized bed, large TV, coffee bar, devoted work space and full bath.

Value · Location · Condition

Coach House at the 1898 Red Bud B & B

Lovingly renovated coach house unit was originally the workshop attached to the back of the coach house. It is a ground floor accommodation with private entrance located behind the main bed & breakfast. We are only two city blocks from Asbury! We make a perfect base to explore the area. The Bourbon Trial, numerous horse farm tours, vineyards, Keeneland, the Horse Park, and historic sites such as Shaker Village of Pleasant Hill. Only 11 miles from Lexington.

Location · Value · Sleep quality

Antebellum Abode

Escape to the heart of horse country with this charming studio apartment, located on a working equestrian facility. Featuring a spacious king-size bed, a full pull-out couch, full bathroom and kitchenette. Wake up to the peaceful sounds of the countryside and enjoy close-up views of majestic horses right outside your door. Just 7 minutes from KY Horse Park and 10 minutes from Keeneland. Whether you're here for relaxation or equestrian events, come enjoy our farm!

Value · Location · Condition

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.

Value · Location · Cleanliness

Horse Farm Cottage near Keeneland and Horse Park

Horse lovers dream and only 5 minutes from the Horse Park! This updated and professionally decorated cottage is located on a beautiful 120 acre horse farm 5 minutes from the Horse Park, 10 minutes from Keeneland and the airport, and 20 minutes from downtown Lexington. There are many activities located close by such as: horse races, horse competitions, Woodford Reserve, Buffalo Trace, and so much more!

Value · Location · Pets

The Barrel | Hot Tub, Sauna & Cowboy Pool

The Barrel is a private one-bedroom guest suite tucked onto 13 beautiful acres in Kentucky horse country. Enjoy the comforts of home with your own private outdoor retreat featuring a year-round hot tub, barrel sauna, fire pit, suspended hammock net, and seasonal cowboy tub. Surrounded by trees, creek views, and horse pasture, it’s a peaceful place to explore by day and soak under the stars by night.

Hospitality · Cleanliness