Whether you’re looking to visit Lexington in style for the weekend or are a local in need of an unforgettable staycation, we’ve compiled a list featuring 20 extraordinary rentals in the Horse Capital of the World that are worthy of a trip for you, your partner, the bestie, or the whole squad this year.
Just a heads up: Prices may vary depending on dates selected, taxes, and booking and cleaning fees (sorry, Airbnb and Vrbo make the rules, we just follow them).
Modern + trendy
Top Shelf
Literally 48 steps above Goodfellas in the Distillery District, you’ll be able to walk home to a rustic, yet modern condo after a fun-filled day of games, cider, and live music.
- ~$343 a night
- 3 BD | 2 BA
- Three balconies, full laundry room, modern kitchen
Lexington’s Carriage House
This 1855 Carriage House is the perfect Instagram-worthy getaway, blending original charm and modern flare, while being conveniently located downtown near Rupp Arena.
- ~$220 a night
- 3 BD | 2 BA
- Two parking spaces, washer + dryer, full kitchen with the basics
Italianate House
Booking this historic 1880s downtown duplex will give guests access to both properties — each featuring beautiful hardwood floors, a kitchen, a living room, and a shared backyard garden space.
- ~$360 a night
- 4 BD | 3 BA
- Three parking spots, washer + dryer, electric vehicle charging
L.A.-inspired Living
The high-end finishes in this two-story modern home will have you questioning whether you’re in LEX or LAX. Enjoy a cozy evening in the on the patio complete with a grill, hot tub, and fire pit.
- ~$250 a night
- 3 BD | 2 BA
- Onsite-parking, spacious private backyard, fire pit
Graffiti House
This unique condo is located within walking distance to some of Lexington’s best restaurants on Jefferson Street. It features simple, sleek amenities with bright mural-filled walls, and a covered parking garage.
- ~$200 a night
- 1 BD | 1 BA
- Washer + dryer, small patio, shower-tub combo
Escape the city
Private Country Estate
Imagine grilling out and relaxing on the comfy back patio while overlooking beautiful Bluegrass farmland, complete with a rescue horse and pet donkeys.
- ~$996 a night
- 5 BD | 5.5 BA
- Gated property, three-car garage, washer + dryer
Seclusion Cabin
This custom-built cabin — complete with new appliances and handmade furniture — sits on two acres in the heart of the Red River Gorge, making it the perfect place for a little R&R.
- ~$220 a night
- 2 BD | 1.5 BA
- Observatory tower, koi pond, and hot tub
O’Neal Cabin
This cozy two-story, 1820s cabin — completely updated in 2019 — offers a peaceful place to rest nestled among 10 acres. Bonus: It’s listed on the National Register of Historic Places.
- ~$150 a night
- 2 BD | 2 BA
- Full kitchen, wood-burning fireplace, beautiful ceiling beams
Bluegrass Country Cottage
Take in the rolling Bluegrass hills with a backdrop of breathtaking sunsets. Then, get some fresh air by roaming the farm or take a short trip to the nearby towns of Versailles + Midway.
- ~$150 a night
- 1 BD | 1 BA
- Pet-friendly, additional sleeping options available, access to walk the farm
Luxury
Historic South Hill Mansion
This expansive downtown home features original 1902 craftsmen woodwork with all the modern upscale amenities — all within a short walk’s distance to Jeff Ruby’s and Rupp Arena.
- ~$5,500 a night
- 6 BD | 4.5 BA
- Downtown parking included, washer + dryer, two living rooms
The Bungalow at 2nd St.
This 1915 fully-updated bungalow offers a blend of glamour and charm in the heart of historic downtown.
- ~$900 a night
- 2 BD | 2 BA
- Wraparound front porch, hot tub, and saltwater pool
New Downtown Luxury
Nestled near the beautiful Transylvania University campus and Gratz Park, this property sleeps up to 13 people with fresh renovations completed in 2022.
- ~$1,200 a night
- 5 BD | 3 BA
- Open-concept kitchen, fire pit, game room, pet-friendly
Historic Castle in Downtown
History and elegance converge at this lavish home that is ideal for both those looking for seclusion from the city and anyone looking to be close to the action.
- ~$471 a night
- 4 BD | 3.5 BA
- Historic details, large kitchen, and outdoor space with a hot tub + firepit
Home away from home
Rosewood Cottage
This charming 1920s cottage boasts a newly renovated kitchen complete with a fresh and relaxing color palette for a touch of elegance.
- ~$270 a night
- 3 BD | 2 BA
- Private fenced backyard, games and books, washer + dryer
Maryland Luxury Downtown Manor
While this space screams vintage chic in the heart of downtown, an indoor slide offers a touch of whimsy in this historic home.
- ~$434 a night
- 2 BD | 2.5 BA
- Features a private backyard and patio
Chevy Chase Charmer
Situated near dozens of restaurants + shopping, this charming bungalow has all the modern amenities and finishes. Go through the gated backyard, and you’ll be treated to a beautifully landscaped outdoor entertainment oasis.
- ~$350 a night
- 3 BD | 2.5 BA
- Two living areas, formal dining room, eye-catching backyard
Themed Gems
Bourbon Hous
This newer construction property is like staying in your own high-end boutique hotel — the perfect place for entertaining during your fun stay in the Bluegrass.
- ~$1,600 a night
- 7 BD | 7.5 BA
- Gaming room, bourbon bar, washer + dryer
The Distillery House
If you like bourbon, horse racing, and a primary suite that opens to a beautiful backyard oasis, this one’s for you.
- ~$350 a night
- 3 BD | 2 BA
- Hot tub, bourbon bar, plush bathrobes
Equine Estate
This sprawling equine estate is located on picturesque Paris Pike overlooking a beautiful horse farm with open-concept entertaining areas and lots of room (inside and out) to relax.
- ~$1,750 a night
- 5 BD | 4.5 BA
- Fire pit, washer + dryer, spacious bedrooms
Homey Horse Farm Hideaway
It wouldn’t be a stay in LEX if you didn’t see a horse up-close-and-personal. Equine enthusiasts will love this cozy farm house that puts you front-and-center on a working farm.
- ~$150 a night
- 1 BD | 1 BA
- Outdoor dining space, wood-burning stove, surrounded by stables.
