House holiday rentals in Lexington

Updated 1910 charm! Walk to Rupp/near Keeneland!

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

Location · Family · View

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Value · Family · Comfort

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

Location · Value · Walkability

The Clayton House | Chic & Cozy

Welcome to our stylish, newly renovated 2-bedroom, 1-bath home, centrally located just minutes away from Georgetown College! This spacious gem boasts an inviting open full-kitchen and living room concept, a back patio, and back yard. Whether you're visiting the college, exploring the town, or simply looking for a comfortable and modern retreat, The Clayton House is the ideal choice for your stay. Experience the perfect blend of convenience and comfort in this newly revitalized space. *No pets

Value · Family · Outdoor spaces

Maryland Luxury Downtown Manor

Our Maryland Manor was designed to be a true Home away from Home.. with an indoor Slide for extra Fun!! Grab coffee, sit in the sleeping porch and slide back down for a refill! A creative, historic oasis perfect for exploring downtown Lexington! Located Downtown, Minutes walk to Rupp, Dining, Galleries, Night Life and Next Door to the Apiary. Paired with Off Street Parking and a large backyard, this stylish place to stay is perfect for group trips. We can’t wait to welcome you to our Home!

Family · Value · Grill

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

Family · Value · Sleep quality

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Family · Value · Accuracy

Close to UK, great outdoor space 15.690.63-2

Absolutely adorable update ideally located within a mile from UK and Kroger Field, and a short walk to the vibrant Southland corridor. Open floor plan with three full bedrooms, including a master suite, and a full basement equipped for recreation or work. Fully fenced backyard retreat is the perfect place to gather for food and drinks by the fire. This cozy gem is the ideal place to experience all that Lexington has to offer. Per city ordinance we cannot allow more than 6 guests.

Family · Value · Comfort

Relaxing Hot Tub | S’mores Fire Pit | Garage

Stay in one of Lexington's most desirable neighborhoods: quiet, safe, & in a low-traffic cul-de-sac that's also close to everything! Create lasting memories with friends & family: - Make s’mores by the fire pit under the stars! - Relax in the hot tub after a long day of travel! - Fenced in yard! - Coffee Bar! Just minutes from favorite local restaurants, shopping, attractions, downtown events, & the interstate (I-75 or I-64). Registration #15076499dash1

Value · Location · Quiet

Cozy 1-bedroom in Lexington

Historical home located in the heart of Lexington, Kentucky. Few minute walk to Woodland Park, Kroger, Starbucks, bars, and restaurants. Gas station right around the corner. A convenient 3 minute drive and you're in the middle of downtown Lexington. Rupp Arena (1 mi), Kroger Field (1.5 mi), Keeneland (7 mi), Kentucky Horse Park (10 mi), Buffalo Trace Distillery (26 mi). 1GB fiber optic wifi. (This home is a duplex.)

Value · Location · Layout

Big Rock Cottage

Charming Cottage located in Downtown Lexington. Completely remodeled - clean and pristine. Two bedrooms and two full baths. Fully equipped kitchen, Waher / Dryer and large back porch. Only 1/2 a block away from Legacy Trail and walking distance to Rupp arena and all downtown activities. Please note that this is located downtown you will see diversity both in culture and socio-economic status. :1506321-1:

Value · Family · Condition

Bourbon Trail ~ Pickleball ~ Hot Tub ~ Mini-Golf

Welcome to this adorable house in the heart of the picturesque bourbon country. It promises a relaxing retreat just a few minutes from local distilleries, scenic countryside landmarks, and exciting attractions. ✔ 3 Comfortable Bedrooms ✔ Full Kitchen ✔ 9-hole Duck Duct Putt-Putt Golf Course ✔ DIY Pickleball Court ✔ Vintage Jukebox ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ Wi-Fi ✔ Laundry ✔ Parking See more below!

Location · Value · Comfort