Guesthouse holiday rentals in Fayette County

4.99 out of 5 average rating, 135 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.

Guesthouse in Nicholasville

4.98 out of 5 average rating, 351 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.

5 out of 5 average rating, 57 reviews

Nordost-Lillegard ( NorthEastSmallGarden)

PLEASE READ THE ENTIRE LISTING freestanding tiny house 500 sq.ft best suited to one person or couple-> one full bed. Lge BR, sleek galley kitchen, off-street prkg inc. space for one horse trailer if @ the horse park/training ctr. Property is fenced, gated, private, safe. There are no cameras inside the guest house.We will be on property while you are here. Licensed By City of Lexington. Convenient Great location for HorsePark, WEI, Rodeo, Dressage, Keeneland. Bourbon trail, UK sports.

4.97 out of 5 average rating, 69 reviews

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.

Superhost

4.87 out of 5 average rating, 23 reviews

Charming Cottage in country setting

Nestled in the heart of the Bluegrass with easy access to 75/64, downtown, Keeneland and Kentucky Horse Park this gated property features award winning gardens and views of neighboring horses grazing and the local peacocks. The perfect place to stay for the races at Keeneland, or horse sales @ both Keeneland or Fasig Tipton. A great place to stay to explore Lexington’s many breweries or The Bourbon Trail. Oh my gosh , I almost forgot… minutes away to watch our beloved Wildcats at Rupp !

4.97 out of 5 average rating, 35 reviews

Guesthouse in Georgetown

Cozy Cottage on Horse Farm

Welcome to The Cottage on Karuna Farm! Located 12 min from Kentucky Horse Park in Georgetown on a cul-de-sac, we invite you to our 10 acre sporthorse farm. Efficiency cottage with one queen bed and a queen pull-out couch, full kitchen, bathroom with shower. Enjoy a relaxing time by our pool, this peaceful and private guesthouse offers a lovely respite after a long day. Sweet, friendly border collie lives on property. Easy access to Lexington, Frankfort, Midway, Keeneland…

4.97 out of 5 average rating, 652 reviews

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 !

4.9 out of 5 average rating, 272 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.

4.96 out of 5 average rating, 154 reviews

Guesthouse in Wilmore

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.

4.92 out of 5 average rating, 193 reviews

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!

4.96 out of 5 average rating, 165 reviews

Modern & Unique Shipping Container

Stay in our unique space in the North Limestone area. The Shipping Container (8X20) features 1 bedroom (queen mattress) + 1 bath and kitchen. We are located 4 blocks from Greyline station. Drive downtown in under 10 minutes, or to Keeneland in just 15. Easy walk to Castlewood Park. Come & explore the artisan culture in our up-and-coming neighborhood.