Also, see which former Wildcats are coming to Rupp this weekend

Home sweet Airbnb

Amazing Airbnb and Vrbo rentals around Lexington

A spacious backyard with a saltwater pool and green turf and patio
The Bungalow at 2nd St. | Photo by Vrbo
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).

Luxury

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
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

Modern + trendy

A bathroom with emerald green tile walls and gray floors

Lexington Carriage House | Photo by AirBNB

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
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

Themed Gems

LEX bourbon haus UCG.jpeg

Bourbon Haus | Photo via Vrbo

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, pet-friendly
10 MORE EXTRAORDINARY RENTALS
Let’s settle this once and for all — what’s the coolest rental home feature?

A. Hot tub
B. Foosball table or pool table
C. Outdoor games like putt-putt
D. Rain showers or jetted tubs
E. An incredible view
F. I don’t care as long as it’s sparkling clean
CAST YOUR VOTE

Click here to have your event featured.

Thursday, Feb. 16
Friday, Feb. 17
  • Presidents’ Day Family Open House | Friday, Feb. 17 | 10 a.m. | Mary Todd Lincoln House, 578 West Main St., Lexington | $0-$10 | Celebrate Presidents’ Day with special programming including games and activities inspired by the activities of the Lincoln family.
Saturday, Feb. 18
  • Discovery Saturday | Saturday, Feb. 18 | 11 a.m.-2 p.m. | Living Arts & Science Center, 362 N. Martin Luther King Blvd., Lexington | Free | Kids of all ages will enjoy STEAM projects, planetarium shows, a meet and greet with the New Orleans Princess, and a fairy friend from Pixie Dust Playdates.
  • ArtWorks Symposium | Saturday, Feb. 18 | 6-9 p.m. | Artworks at Carver School, 522 Patterson St., Lexington | Free | Celebrate Black History Month with printmaking activities, food trucks, as well as stories from inspiring guest speakers.
We have a calendar filled with events and activities you can plan for in advance. Click the button below to bookmark ideas for upcoming date nights, family outings, and time with friends.

100+ MORE EVENTS

Weather
  • 65º | Strong storms + wind | 94% chance of rain
Community
  • The City of Lexington has donated East End’s historic Palmer Pharmacy building to United Way of the Bluegrass. It will now be known as the Marksbury Family WayPoint Center at the Historic Palmer Pharmacy Building and serve the community with vital resources and programming.
Sports
  • UK men’s basketball teams from the 1996, 1997, and 1998 seasons will be honored at this Saturday’s home game against Tennessee at 1 p.m. Fans can expect to see former players like Derek Anderson, Anthony Epps, Cameron Mills, Jeff Sheppard, and Wayne Turner celebrate 25 years of their dominant run. (Lexington Herald-Leader)
Eat
  • Dust off your March Madness skills... with donuts. North Lime Coffee + Donuts Donut Madness 2023 will run from March 3 to April 7. Customers can fill out a bracket to help their favorite flavor compete for the crown (and get a chance to win a $200 gift card). 🍩
Arts
  • Community Ventures and Art Inc. KY will host “The Art of Approaching Galleries to Represent Your Work” virtual workshop on Saturday, Feb. 18 at 10 a.m. Led by local retired gallery owner Mary Rezny, aspiring artists can sign up to get one-of-a-kind guidance. 🎨
Closing
  • Dogwood Home Furnishings, located at 1591 Winchester Rd., is closing its doors on March 31, as the owners are retiring. If you’re in the market for new furniture, artwork, lighting, and home decor, stop by 10 a.m.-6 p.m. Monday-Saturday to shop its retirement sale.
Travel
  • Ready to plan springtime adventures? A ~5 hour drive from LEX, Greenville, SC is filled with natural beauty, outdoor activities + dining delicacies. Pro tip: Order a free Visitor’s Guide to start planning your trip, and check out VisitGreenvilleSC’s Instagram for itinerary inspo.*
  • How does Going (formerly Scott’s Cheap Flights) work? Sign up for free, follow up to five airports, and Going will notify you when flights are 40-90% off. Bonus: You can browse deals immediately after signing up (like a $500+ flight to Italy). 🍝*
Wellness
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THE WRAP

Today’s issue was written by Molly.

Editor’s pick: This Saturday, Feb. 18 at the Texas Roadhouse on Richmond Road is the 2023 Polar Plunge benefiting Special Olympics of Kentucky, and the Lexington Sporting Club wants you to join them. Learn more.

Missed yesterday’s newsletter? See our ideas for taking a mental health day in Lexington.
Connect with us.

Editorial: Molly Thompson, Britt Thorson, Emily Shea, Jessalin Heins-Nagamoto, Dayten Rose, Sarah Leonhardt, Katie Smith | Send us a scoop, question, or feedback.

Sales: Marin Fiske | Advertise with us.

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