Holiday rentals in Lexington

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Top-rated holiday rentals in Lexington

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Train in Lawrenceburg

4.98 out of 5 average rating, 260 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

21–28 Mar

£138 per night

Guest favourite

Farm stay in Nicholasville

4.93 out of 5 average rating, 240 reviews

Moonlit Meadows: A Tranquil Getaway for Travelers

Escape to the heart of Kentucky's countryside in our modern guest suite, set across a 17-acre landscape. Immerse yourself in the serenity of nature with views of a pond and beautiful rolling fields. Ideal for both business and leisure travelers as well as those visiting Asbury University. Our guest suite has continued to offer a tranquil haven where you can relax and rejuvenate! Enhance your experience by visiting the great grandson of the legendary Secretariat, stabled just 4 miles away.

19–26 Aug

£95 per night

Guest favourite

Home in Lexington

4.83 out of 5 average rating, 479 reviews

Modern and Spacious Home w/ 5.1 Theater

(Also click my host picture to see our newest Airbnb "Elegant & Inviting Home with 5.1 Theater") Open space, natural light, and charming décor greet you at our well-adorned duplex in the established Merrick area in Lexington! Walk to Malone’s, Baskin Robbins, Fresh Market, and many other nearby shops. Bask in modern furnishings, memory foam beds, equipped kitchen, full-size laundry room, and high speed Wi-Fi. Movie nights are a blast with the huge 84” projector screen and surround sound!

6–13 Oct

£98 per night

Guest favourite

Flat in Lexington

4.94 out of 5 average rating, 195 reviews

Enjoy Downtown Lex from your Private Deck

Walkable to downtown, Rupp/Convention Center, Town Branch Distillery & less than 1 mi to UK student center. 12 min drive to Keeneland, 19 min to horse park. Sleeps 2-3 with 1 queen size bed and a couch bed. Equipped with basic kitchen amenities, all new appliances, washer/dryer, 2 Smart TVs & WIFI. Bedroom features a glass garage door that opens to a private patio. This apartment is located in a brand new building with free parking on premises. Energy efficient, simple, center of it all!

13–20 Aug

£102 per night

Guest favourite

Flat in Lexington

4.98 out of 5 average rating, 490 reviews

Haven on High Street Private Apt Historic Home

Haven on High St. Quiet-gracious-comfy-one bedroom apartment in 1842 home. Off street parking. King bed in bedroom, comfy queen sofa bed in living room, claw foot tub. Eclectic decor-a visual artistic treat. By design, the space is not kid or pet friendly. Fully furnished kitchen+coffee, tea, snacks. Private apartment-shared courtyard. Walk to coffee shop, UK, Rupp, downtown dining. Beautifully landscaped gardens with patio and porch seating. Host lives next door and available-as needed.

25 Feb – 4 Mar

£87 per night

Guest favourite

Home in Versailles

4.93 out of 5 average rating, 120 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

19–26 Mar

£123 per night

Guest favourite

Guest suite in Lexington

4.98 out of 5 average rating, 124 reviews

Close to Keeneland Charming Guest Suite

Great location in beautiful well established neighborhood. 5 mi to Keeneland & airport, 2 mi to downtown, Rupp Arena, Univ of Kentucky campus & football stadium. Centrally located within one mile of all major hospitals. Lexington is located along the Kentucky Bourbon Trail. Enjoy distillery, horse farm & historic home tours, unique and fine dining, craft breweries, sporting events, theater, concerts, boutique shopping. Nearby horse farms, rolling hills, hiking and boating/canoeing

14–21 May

£78 per night

Guest favourite

Flat in Lexington

4.94 out of 5 average rating, 127 reviews

Charming & Cozy in Downtown Lexington

316 Hampton Court was designed for vacation rentals 110 years before the first air mattress was rented out on Airbnb. Built as apartments in 1920 on land owned by the Stoll family and named for their son in law, The Howard was bought and completely renovated in 2007. Now it has several vacation rentals behind its historic rounded door and up its oak staircase. This apartment is a cozy 650 square feet and was professionally reconfigured by one of Lexington's finest architects.

31 Aug – 7 Sept

£106 per night

Guest favourite

Home in Lexington

4.92 out of 5 average rating, 639 reviews

Updated historic home! Walk to Rupp/UK/restaurants

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This newly 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.

18–25 Aug

£134 per night

Guest favourite

Flat in Lexington

4.9 out of 5 average rating, 129 reviews

Lovely Downtown Apt 1 Block from Rupp!

Walk to Rupp and all downtown has to offer from this cozy, one bedroom apartment. The space is outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in downtown Lexington. If this is your first time booking with us, welcome! We look forward to hosting you again soon. if you have stayed with us before, thanks for your loyalty.

6–13 Nov

£103 per night

Guest favourite

Barn in Lexington

4.93 out of 5 average rating, 292 reviews

Stay with our horses and goats on a private farm

Lovely and private studio barn apartment in super safe neighborhood. Stay with our horse and goats on 12 private acres, minutes from downtown Lexington. Hiking trails around property, and just minutes to several state parks. Three miles to 75 and 64, and 15 minutes to downtown Lexington, the Kentucky Horse Park, UK campus, and 10 minutes to the Hamburg area of Lexington full of restaurants, sports bars, and movie theaters. 50 amp EV charging station

28 Dec – 4 Jan

£85 per night

Guest favourite

Home in Lexington

5.0 out of 5 average rating, 115 reviews

Nomi House, Renovated 1880's shotgun, downtown Lex

Registration ID '15082764-1' Enjoy your stay in comfort and style at the newly renovated NOMI House. Perfectly located in downtown Lexington, KY, walking distance to all the best restaurants and event spaces. Easy drive to equine experiences and the rolling hills of the Bluegrass state.

23–30 Aug

£119 per night