Holiday rentals in Lexington

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Lexington

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

0 of 0 items showing

1 of 3 pages

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.

17–24 Aug

£96 per night

Guest favourite

Home in Lexington

4.92 out of 5 average rating, 159 reviews

My Old Kentucky Home

Historical home located in the heart of Lexington, Kentucky. One 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). Home has G-Assistant so you are able to control lights, speakers, and thermostat. YouTubeTV and Netflix provided as well.

18–25 Aug

£103 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.

10–17 Nov

£90 per night

Guest favourite

Flat in Lexington

4.98 out of 5 average rating, 390 reviews

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

21–28 May

£143 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

17–24 Mar

£123 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.

15–22 Jul

£140 per night

Guest favourite

Home in Winchester

4.91 out of 5 average rating, 672 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

23–30 Jun

£53 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.

9–16 Dec

£103 per night

Guest favourite

Guest suite in Lexington

5.0 out of 5 average rating, 112 reviews

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!

23–30 May

£104 per night

Guest favourite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 441 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

1–8 Mar

£102 per night

Superhost

Cabin in Lexington

4.81 out of 5 average rating, 441 reviews

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

27 Jan – 3 Feb

£83 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

1–8 Jan

£85 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Lexington holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Lexington's top sights

Rupp Arena140 locals recommend

Keeneland164 locals recommend

Hamburg Pavilion46 locals recommend

Fayette Mall38 locals recommend

Kroger Field34 locals recommend

The Kentucky Castle60 locals recommend

Other great holiday rentals in Lexington

Guest favourite

Guest house in Lexington

4.97 out of 5 average rating, 261 reviews

Fully sanitized, private Carriage House + King Bed

15–22 Sept

£113 per night

Guest favourite

Guest suite in Lexington

4.98 out of 5 average rating, 124 reviews

Close to Keeneland Charming Guest Suite

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

9–16 Dec

£106 per night

Guest favourite

Guest house in Nicholasville

4.98 out of 5 average rating, 295 reviews

Cottage Retreat - Wine, Horses, Convenient

8–15 Aug

£90 per night

Guest favourite

Home in Lexington

4.91 out of 5 average rating, 563 reviews

Lower Level of Home near UK, Eateries, 1000 sq ft

19–26 Aug

£80 per night

Guest favourite

Loft in Lexington

4.95 out of 5 average rating, 429 reviews

UNIQUE!! 1BR Loft-Rupp-Downtown w/ Many Extras.

15–22 Jan

£79 per night

Guest favourite

Flat in Versailles

4.99 out of 5 average rating, 265 reviews

High style on the Bourbon Trail

9–16 Dec

£115 per night

Guest favourite

Home in Lexington

4.87 out of 5 average rating, 371 reviews

Elegant & Inviting Home w/ 5.1 Theater

22–29 Sept

£102 per night

Show all

Quick stats about holiday rentals in Lexington

Total rentals	1.6K properties
Rentals with dedicated workspaces	850 properties have a dedicated workspace
Rentals with a pool	100 properties have a pool
Pet-friendly rentals	630 properties allow pets
Family-friendly rentals	1.1K properties are a good fit for families
Total number of reviews	90K reviews

Holiday rentals in Lexington

Top-rated holiday rentals in Lexington

Farm stay in Nicholasville

Home in Lexington

Flat in Lexington

Flat in Lexington

Home in Versailles

Home in Lexington

Home in Winchester

Flat in Lexington

Guest suite in Lexington

Cabin in Lawrenceburg

Cabin in Lexington

Barn in Lexington

Holiday rentals for every style

Flats

Cabins

Cottages

Popular amenities for Lexington holiday rentals

Stay near Lexington's top sights

Other great holiday rentals in Lexington

Guest house in Lexington

Guest suite in Lexington

Flat in Lexington

Guest house in Nicholasville

Home in Lexington

Loft in Lexington

Flat in Versailles

Home in Lexington

Quick stats about holiday rentals in Lexington

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore