Holiday rentals with breakfast in Fayette County

*New* Run for the Roses Retreat! 2 King beds/I-75

Conveniently located 5 miles from UK, 6 miles from Rupp Arena, 18 minutes to The Kentucky Horse Park, and minutes from shopping and restaurants! 2 master bedrooms with king beds and Jack and Jill en-suite bathrooms. One master on first floor and one upstairs! 4 - 92” Smart TVs with Roku Kids playroom and lots of board and outdoor games = fun Outdoor space is cozy and packed with fun! Put-put golf, giant connect 4, kid friendly Axe throwing etc making this area the favorite! Oh and WAFFLES!!

Warfield Manor/ Walk to Greyline Station

Located just 5 minutes from downtown Lexington, Warfield Manor is a beautiful newly renovated home featuring 4 bedrooms & 3 bathrooms. Located on the historic farmland of William Warfield guest will #LiveLikeALocal by being 20 minutes from Keeneland & the Bluegrass Airport, 15 minutes from Kroger Field, & 5 minutes from Rupp Arena! Enjoy your morning coffee on our cozy porch or even cocktails in the aesthetically pleasing back yard by our firepit. We have no doubt that you will feel at home!

Cozy Retreat-Hot Tub-Fire Pit-Gym-Chevy Chase

Welcome to a luxurious home and perfect spot for large gatherings with 6 bedrooms and 5 bathrooms. This property has beautifully designed common areas on the main level and an expansive living room with big screen television and comfortable seating. Two master suites with large king beds with ensuite bathrooms and double vanities. Four modern bedrooms with Queen Size beds. Enjoy a hybrid of luxury with full access to our entire property with firepit, large deck, hot tub and garage gym.

Downtown/UK, Private, Quiet (Local ID 15067121)

Perfect for two guests without disabilities. No elevator. Spacious, third floor, walk-up studio apartment with private parking in a completely renovated historic professional office building near downtown Lexington. Everything downtown has to offer is nearby: Rupp Arena, gym, restaurants, nightlife, UK, and post office. Near everything, yet quiet, secure and private. Two HDTV's, new separate A/C & heating system, fully stocked kitchenette and bath, huge closet, memory foam queen size bed.

Lovely Private Suite • Walk to Rupp • Free Parking

Historic charm meets modern comfort in this private 2-bed, 2-bath upstairs suite in Lexington’s Woodward Heights, steps from Rupp Arena. Ideal for 4 guests (rollaway for 5th guest available), this retreat offers free off-street parking, easy self check-in, upgraded streaming, and a kitchenette with fridge, microwave, air fryer, and coffee maker. Perfect for families and event-goers seeking a home base in a peaceful residential area. Located in a beautifully preserved 1888 historic home.

Nonie's Abode

Located in quiet Meadowthorpe subdivision, this duplex apartment is convenient to downtown, The Commons, Keeneland, UK, Masterson Station Park, McConnell's Springs, the Legacy Trail, the airport and the Horse Park. There is a grocery store within 0.6 mile. Very walkable neighborhood. It is also near the distillery district with outdoor music events, food and bars. There are multiple places to eat within walking distance. Owner/host lives in other side of duplex.

Linden Place LLC

Our cabin is on gated property in the middle of Bluegrass horse country with a an indoor and outdoor private shower and sits on the back of 5 landscaped acres for maximum privacy. Close to the Ky Horse Park! Incl., YouTube TV, WiFi, deluxe king bed, & private deck overlooking pastures. Snacks, tea/coffee and breakfast items provided. Please note there will be a pet fee of $25/Nite/pet with a max weight of 35lbs. Fees will be requested after booking.

Pet-Friendly Cozy Retreat 10 mins to Horse Park

Experience equestrian chic at The Layover House, a renovated 3-bed, 2-bath home in Georgetown. Perfect for families or groups, our home offers vintage charm with modern comforts. Ideally located just 10 mins from the Kentucky Horse Park and 20 mins from Lexington's distilleries and downtown. Enjoy a private backyard with a fire pit, a fully equipped kitchen, and premium amenities. Your perfect base for exploring the Bourbon Trail and horse country!

Bell Ct-133 N Ashland Ave-Horse Park-Bourbon Trail

A great home if you are coming to KEENELAND, THE HORSE PARK, BOURBON TRAIL, or a WEDDING. 5 Star reviews say it all! Located at 133 N Ashland in historic Bell Court, only 5 minutes to DOWNTOWN LEXINGTON, 7 minutes to RUPP ARENA, 6 minutes to UK & UK's football stadium. Close to restaurants, shops, brewery, incl.the trendy areas of Chevy Chase & National Avenue. Walk to many of these places . Great place to stay if you are here for work.

Historic Cottage, Old Fashioned Hospitality!

We welcome all people! We don't care who you love or what shade of skin you're in. You are most welcome in our home. Take a step back in time at Kring Cottage in central Georgetown. This charming and historic craftsman has been welcoming people since 1926. With four beautiful bedrooms and 2 bathrooms, there is plenty of room for your whole crew. She is cozy and comfortable with a vintage flair, but with all of the modern conveniences.

The Bourbon Barrel on Wyatt-Fenced in yard

This 2 bedroom, 1 bathroom bourbon-themed home will have you feeling like a Lexington, KY native the second you walk in the door. This property includes a spacious kitchen, cozy bedrooms, & a huge fenced in backyard! The Bourbon Barrel is located in the heart of Lexington & is just minutes away from Chevy Chase, Downtown, Hamburg, and I-75. No matter what brings you to Lexington, this is the perfect place to stay!

Walk to UK & Kroger Field | Fire Pit | Sleeps 8

Stay just minutes from UK campus, Kroger Field, Rupp Arena, Keeneland, and downtown Lexington! This cozy 3-bedroom home with 4 beds sleeps 8 comfortably and features king and queen beds, a private backyard with a fire pit, free parking, and a fully stocked coffee bar. Perfect for game days, Keeneland trips, family visits, or downtown getaways! Keyless entry makes check-in simple and stress-free.