Holiday houses in Lexington

4.92 out of 5 average rating, 152 reviews

Farm stay in Winchester

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

4.98 out of 5 average rating, 322 reviews

Apartment in Wilmore

Basement apt. w/private entrance & kitchenette

Our full basement apartment with private entrance is modest but comfortable. Located within one mile of Asbury Seminary and University, our space is ideally suited for commuting students, out-of-town guests, or folks visiting the beautiful Bluegrass region. Our home is a 15-minute walk from the campuses and business district. We are a family of six and you will occasionally hear our boys upstairs, but as a Christian family, we strive to treat our guests as we would want to be treated. Reg. 9485

4.93 out of 5 average rating, 776 reviews

Restored charm! Walk to Rupp. Easy Keeneland drive

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 or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

Guesthouse in Nicholasville

4.98 out of 5 average rating, 348 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.

4.88 out of 5 average rating, 482 reviews

Townhouse in Lexington

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

Superhost

4.92 out of 5 average rating, 588 reviews

KY & Bourbon & Horses, Oh My! Close to Keeneland

This home has been completely renovated with flawless finishes and top of the line appliances. This is for the UPSTAIRS only. (No one else lives at the residence & is solely for Airbnb) 10 minutes from Keeneland & a few miles from hospitals. Convenient location to shopping and restaurants. Clean and comfortable living spaces. This is a chefs kitchen, that has double doors to a walk out patio. The bathroom has a Bluetooth fan. I’ve provided everything to make your trip enjoyable as possible.

4.81 out of 5 average rating, 266 reviews

The Loft @ West Second

Walk to Downtown! Located on West 2nd Street. Walkable to downtown and Rupp Arena and a block from trendy Jefferson street. This uniquely designed space will soothe and refresh after a long day of adventuring or bourbon tasting. Rupp Arena, The Civic Center, Triangle Park, The Burl and Distillery District and all that Downtown Lexington has to offer is at your fingertips. The University of Kentucky is less than 2 miles away, KY Horse Park and Keeneland are all within a 15 minute drive

4.96 out of 5 average rating, 200 reviews

Location! Beautiful Downtown Apt, Across from Rupp

Beautiful, fully renovated (2021) apt in a historic building on Spring Street--as close as you can be to Rupp Arena and the Convention Center. PARKING IS AVAIL. You can walk to everything! Coffee shops, restaurants/bars & anywhere in downtown Lexington! Extra spacious & outfitted with comfortable furnishings, plush linens, basic kitchen amenities & new appliances. The home includes WIFI and two ROKU Smart TVs. Enjoy your morning coffee from the comfort of your large, private porch.

4.95 out of 5 average rating, 206 reviews

Canopy of trees

Enjoy this peaceful and centrally-located apartment. Across the street from the historic Henry Clay estate. Just a few miles from Rupp arena, Uk, stadium and downtown. A short drive to the horse park. Walking distance to restaurants. There is a $50 per pet fee. Please be sure to include pet in your booking. This is a one bedroom with a queen bed. The couch folds into a sleeper and there are curtains for privacy.. Street parking only. The back and driveway are our private areas

4.91 out of 5 average rating, 263 reviews

Guesthouse in Lexington

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.

4.97 out of 5 average rating, 116 reviews

Summer Bliss! Pool&FunZone Oasis! Hottub! GameRm!

Your friends and family will be centrally located in a peaceful Cul-de-sac in Lexington with all the perks! Whether you are going to Keeneland, a sporting event, or just looking for a fun getaway, we have all the entertainment you need! Featuring a pool, hot tub, arcade machine, pool table, ping pong, air hockey, and shuffleboard table! Looking to just relax? Help yourself to our complimentary coffee bar and take in the cozy sounds by our fire pit in the back yard!

4.99 out of 5 average rating, 197 reviews

Guest suite in Lexington

The Gainesway Suite-Near UK/Hospitals/Keeneland

A posh Guest Suite in popular Gainesway! Centrally located in a friendly, established neighborhood. Minutes to Lexington's best Concert Venues, Restaurants, UK, Rupp, Hospitals, and Shopping! Private entrance, luxurious and stylish furnishings, plus your own laundry room! Perfect for a night in town, traveling for a ballgame or show, visiting our famous distilleries and Keeneland! The suite is also equipped for longer stays, business travelers, you name it!

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Popular amenities for Lexington holiday rentals

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Other great holiday rentals in Lexington

5 out of 5 average rating, 55 reviews

Tiny home in Lexington

Horse & Barrel Haven

CaitlanRating, 5 stars1 week ago

We had a great time! We loved being here & being able to come to a cozy place after a fun horse day!

4.95 out of 5 average rating, 84 reviews

Cabin in Paris

1791 Cabin on Historic Horse Farm

AmandaRating, 5 stars2 weeks ago

Jessica was a wonderful host; kind and thoughtful. The cabin was exactly as described. It was clean and comfortable. Waking up to the chirping birds and seeing the horses grazing was fantastic.

5 out of 5 average rating, 38 reviews

Centrally Located Lex Apartment!

GabrielaRating, 5 stars1 week ago

This place is truly a rare find. Centrally located yet very quiet. The apartment was spotless and so beautifully decorated. Elegant, comfortable, and welcoming. Every room looked exquisite and had everything that someone could possibly need while away from home. The kitchen was well equipped with everything. The little balcony was perfect for hanging out in the evening. The apartment is only few minutes walk from the downtown restaurants. This was an absolutely perfect place.

5 out of 5 average rating, 67 reviews

The Kenwick Pied-à-terre

ZacharyRating, 5 stars2 months ago

This place was perfect for the weekend. Close to downtown and one block away from the community center, playground and coffee shop. Sidney and Austin were great hosts and were accommodating all weekend.

Superhost

Cottage in Winchester

4.9 out of 5 average rating, 90 reviews

Life is Better On The River

TimRating, 5 stars1 week ago

Was a wonderful place to stay

4.95 out of 5 average rating, 39 reviews

Apartment in Georgetown

The Fort in Georgetown

ShannonRating, 5 stars1 week ago

My husband and I enjoyed our stay at The Fort. Historic Georgetown was beautiful, the house was easy to find, and Camille was easy to communicate with. We appreciated how clean everything was, the comfy couches, beautiful kitchen and easy to adjust temperature. We would definitely stay here again.