Guesthouse vacation rentals in Lexington

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Top-rated guesthouse rentals in Lexington

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Guest favorite

Guesthouse in Lexington

4.97 out of 5 average rating, 68 reviews

Modern & Luxurious Carriage House at Warsaw

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, KY Horse Park, Lexington Country Club, Keeneland, Fasig-Tipton, downtown Lexington, UK, Red Mile, Rupp Arena, dining, shopping & more!

Guest favorite

Guesthouse in Lexington

4.99 out of 5 average rating, 97 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.

Guest favorite

Guesthouse in Nicholasville

4.98 out of 5 average rating, 323 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.

Guest favorite

Guesthouse in Lexington

4.92 out of 5 average rating, 91 reviews

"Clay Cottage" at Woodland Park- Artistic & Cozy

(2 night minimum- great for extended stay) This charming cottage was an artists's studio- converted into a compact living space full of handmade character. Centralized hub for Lexington. Walkable neighborhood. Univ. KY within walking distance- 7 mi to Keeneland, 15 min drive to Ky Horse Park, Grocery 1.5 blocks away, nearby local restaurants. Quiet & secluded, although on the edge of downtown. Across from the nicest park in LEX. Wonderful peaceful hideaway downtown! Excellent Location!

Guest favorite

Guesthouse in Lexington

4.92 out of 5 average rating, 183 reviews

Horse Farm Cottage near Keeneland and Horse Park

PROFESSIONALLY SANITIZED EVERY VISIT! 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! In addition, the farm can also be rented out as a wedding and events venue. https://www.antebellumfarm.net/home

Guest favorite

Guesthouse in Georgetown

4.96 out of 5 average rating, 28 reviews

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…

Guest favorite

Guesthouse in Lexington

4.96 out of 5 average rating, 595 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 !

Guest favorite

Guesthouse in Lexington

4.93 out of 5 average rating, 182 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.

Guest favorite

Guesthouse in Wilmore

4.96 out of 5 average rating, 148 reviews

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.

Superhost

Guesthouse in Nicholasville

5 out of 5 average rating, 4 reviews

Breathtaking Horse Farm views, private! Keeneland!

Welcome to the Kinlark Guesthouse, nestled in the heart of horse country on a 10 acre estate. Wake up each morning overlooking horse paddocks and rolling hills. Fully equipped & renovated home with private parking area and deck. This space is the perfect retreat for your visit to Kentucky! 5 acre paddock available as an added amenity. *Please note, each guest on the reservation must be approved by hosts prior to booking.

Guest favorite

Guesthouse in Lexington

4.95 out of 5 average rating, 39 reviews

Conveniently located to UK, Keeneland and Hamburg

Your family will be close to everything when you stay at this centrally-located place. Whether you’re here for UK games, Keeneland, Bourbon trail, this home is perfect for you! Located right off the interstate! 3 bedrooms, 2 bathrooms, and is fully stocked!