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 15 of some 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 gram-worthy getaway blending original charm and modern flare, and is 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
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
- All the essentials plus an 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
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 and 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
- Smart TV, wraparound front porch, hot tub, and saltwater pool
New Downtown Luxury
Right near the beautiful campus of Transylvania University and Gratz Park, this property sleeps up to 13 people with fresh renovations completed in the fall of 2022.
- ~$1,200 a night
- 5 BD | 3 BA
- Open-concept kitchen, fire pit, game room, pet-friendly
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
Wildcat Hideaway I
UK fans will love the close proximity to both Kroger Field and Rupp Arena, with a spacious backyard area for entertaining.
- ~$255 a night
- 3 BD | 1 BA
- New appliances, backyard entertainment space, pet-friendly
White House
Conveniently located to Woodland Park and Chevy Chase neighborhood, this 1890s bungalow is full of historic charm with modern upgrades and amenities.
- ~$160 a night
- 2 BD | 1.5 BA
- Clawfoot tub, kitchen cooking essentials, front and back porches
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
- Bar and gaming room, memory foam mattresses, 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, fully-stocked 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
