Guesthouse vacation rentals in Lexington

Cozy 1 bedroom cottage on picturesque horse farm

Welcome to The Cottages at Oxford Springs Farm. Enjoy a quiet stay in this newly remodeled cottage. One of 3 rental spaces on this property, this unit provides a cozy space with views from every window that capture the beauty of a small working thoroughbred farm. Conveniently located only 10 miles from the Ky Horse Park, 5 miles from the quaint historic town of Georgetown and 30 minutes from some of Kentucky's greatest bourbon distilleries. For Wildcat fans, Rupp Arena is only 15 miles away.

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.

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.

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.

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 !

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

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.

Cozy Cottage Downtown Versailles

Rose Hill Cottage, built in 1877, sits in the heart of the Rose Hill Historic District of Versailles, KY. Enjoy your best night's rest with our hand-selected luxury bedding. Take a soak in the original, restored claw-foot tub. Relax on the porch while you sip your morning coffee. With the best of the old and the new, a stay at Rose Hill Cottage is sure to transport you back in time. Breakfast is included.

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!

Richmond Guesthouse

Private country apartment between Richmond and Berea. Enjoy quiet time away from the city but you are still just a short drive away from all the amenities. We have everything you could need for a one night stay or longer. There is livestock in the adjacent fields but won't be a bother to you. There is free wifi and a roku hooked up to the tv so you can access all of your streaming services.

The Carriage - Quaint Haven steps to the Capitol

Ignite your winter adventure with a chic Parisian-style hideaway in Historic Frankfort! Just minutes from 13 iconic distilleries and the KY Capitol, this cozy retreat offers fast Wi-Fi, smart TV, full kitchen, private entry, and free parking. Unwind in a plush queen bed and sip coffee or wine on the bistro deck. Warm, charming, and made for unforgettable cold-weather memories worth toasting.