10 Unique Airbnbs For Your Next Lexington-Area Event

I’m a big fan of Airbnb and Vrbo. I’ve booked accommodations through these sites everywhere from Rebecca Farm to Red Hills, Luhmühlen to LRK3DE, Badminton to Boekelo. Not only can they be cheaper than a hotel (always a plus for EN, on our quest to cover every important event in the world with a budget of literally zero dollars), they often have character and help create memories in a way that cookie cutter chain hotels just can’t.

In a new series, we are combing Airbnb listings for unique places to stay in some of the most popular eventing destinations. Previous editions: OcalaAiken, Tryon, Rocca di Papa (site of the 2022 WEG). Today we head to Lexington, Kentucky.

Photo via Airbnb.

Vintage Airstream/Downtown

If the idea of camping appeals to you — except for the part about having to set up a tent, and lack of heat/air conditioning or really any basic modern amenities whatsoever — you’re the target “glamping” demographic. This vintage 1960 Airstream is located in downtown Lexington, but feel free to close your eyes and pretend you’re out in the wilderness. It has loads of character and sits behind an 1890 Victorian House with fenced yard, fire pit and outdoor dining area.

Photo via Airbnb.

The Dairy Dream Farm Stay

Moo-oove over, hotels! Three cozy cow-themed bedrooms await guests on this working dairy farm. This would be an especially fun stay for kids, who can experience milking cows, collecting chicken eggs, and play time with sheep and goats. Free coffee, tea and fresh farm eggs for breakfast included. A portion of your stay contributes to the program at Stack-a-Story Inc. to provide farm stays for the underserved.

Photo via Airbnb.

ARCADIA FARM COTTAGE – Luxury Bluegrass Retreat

The word “Arcadia” is often used to describe an idyllically pastoral place, and that checks out with this three-bedroom, four-bath cottage. Located on a historic 384-acre farm, it features include Tempur-pedic mattresses fitted with luxe linens, king bedrooms, classic equestrian decor and a patio with panoramic views.

Photo via Airbnb.


“Is this our Airbnb or are we just at a cool but really empty club?” This downtown loft with a city skyline view is the perfect place to recreate the vibes of Meg Kep’s early “Creepy Dance Party” videos in a more appropriate setting. Includes HDTV with every possible subscription (Hulu, HBO Max, Disney+, Amazon Prime Video, premium cable, Netflix, Apple TV, etc.) and some crazy lights.

Photo via Airbnb.

Estate in The Heart of Horse Country

Looking for a luxury horse show getaway with up to a dozen of your closest barn buds? This opulent five-bedroom, five-bath estate is adjacent to a working winery and overlooks a stately horse farm. It’s the perfect place to kick back with a glass of bubbly and imagine yourself the silk-stockinged owner of a fleet of champion race horses.

Photo via Airbnb.

Unique Stay – 1907 Log Cabin Near Kentucky River

This 1907 log cabin is a bit of a haul from the Horse Park but it’s so unique, we couldn’t leave it out. Perched on the palisades of The Kentucky River, it has king bedroom and a fun two-bed loft (ladder access, of course!) The hosts recommend dinner at the nearby Proud Marys BBQ, and if you’re luck you’ll catch some live music.

Photo via Airbnb.

Modern & Bright Tiny House

No Airbnb highlight reel would be complete without a tiny house (or two!) This one looks like a dollhouse but actually can sleep up to four; it was built and lived in by its hosts until their family started to grow. Here’s another cute one in the area: Purple Door Tiny House.

Photo via Airbnb.

Bourbon Hous – 7 Bdrms, Bar, Billiards, Brand New!

Why go out on the town when you can just stay in? In my experience stay-at-home bartenders mix the strongest drinks, too. This renovated historic house has seven bedrooms and seven and a half baths, making it a fun place for your whole barn crew to stay.

Photo via Airbnb.

 Enjoy Downtown Lex from your Private Deck

This breezy one-bedroom, one-bath loft makes me want to rip out every wall in my house and replace it with a garage door. Brilliant! So cute and cozy and equipped with basic kitchen amenities, all new appliances, washer/dryer and two TVs. About 20 minutes from the Horse Park.