Places to stay near Rupp Arena

4.93 out of 5 average rating, 934 reviews

A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.

Home in Lexington

Updated 1910 charm! Walk to Rupp/near Keeneland!

If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This renovated Victorian home in downtown Lexington is within walking distance of excellent dining, distilleries, and entertainment. Attend a concert/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

A stylish bedroom features a spacious bed with light grey bedding and a decorative throw. Natural light fills the room from multiple windows, complemented by a ceiling fan and wooden beams above. A small seating area and a blue dresser add functional elegance.

4.92 out of 5 average rating, 320 reviews

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Pioneer Split Units for AC and Heat. Free parking for easy access to conventions, concerts, and games.

4.96 out of 5 average rating, 150 reviews

A spiral slide in vibrant burgundy extends from a wooden ceiling to the floor, creating a playful focal point in the space. Natural light filters through windows, illuminating the smooth wood flooring and surrounding area, which includes modern appliances and a stylish chair.

Home in Lexington

Maryland Luxury Downtown Manor

Our Maryland Manor was designed to be a true Home away from Home.. with an indoor Slide for extra Fun!! Grab coffee, sit in the sleeping porch and slide back down for a refill! A creative, historic oasis perfect for exploring downtown Lexington! Located Downtown, Minutes walk to Rupp, Dining, Galleries, Night Life and Next Door to the Apiary. Paired with Off Street Parking and a large backyard, this stylish place to stay is perfect for group trips. We can’t wait to welcome you to our Home!

4.94 out of 5 average rating, 269 reviews

An open living area features large glass doors that provide views of the greenery outside. Industrial elements, such as exposed beams and metal accents, complement a cozy seating arrangement with a sectional sofa and wooden coffee table. A dining table with bar stools is visible in the background.

Condo in Lexington

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

4.89 out of 5 average rating, 271 reviews

The historic townhouse is showcased from the street, featuring a two-story facade with large windows and a decorative balcony. A tree is positioned in front, while outdoor seating is visible on the sidewalk. The building is bordered by brick and modern structures, reflecting downtown Lexington.

Townhouse in Lexington

The Statesman / Walk to Rupp / Superb Deck

The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

Superhost

Two comfortable armchairs are positioned facing each other, adorned with contrasting black and brown cushions. A small wooden table is placed between them, featuring a colorful book about horses. A large, framed artwork of a horse and rider decorates the wall behind.

4.8 out of 5 average rating, 301 reviews

Historic Distillery View Apartment. KING BEDS!

Enjoy a stylish experience at this centrally-located apartment. Our historic Airbnb is located in Lexington’s first boarding house. Originally built in the 1800s as a place for travelers to stay as they passed through town. We are bringing the boarding house back to its initial intention. Thoughtfully decorated with comfort in mind you can sit back and relax while enjoying our cotton sheets, comfortable sofa, and unique touches that will make you feel like you live in a historic palace.

A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.

4.98 out of 5 average rating, 563 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

A stylish living area features a spacious sofa adorned with decorative pillows, complemented by a glass coffee table. An ornate gold-framed mirror adds elegance to the wall, while a nearby lamp and art pieces create a cozy yet sophisticated ambiance.

4.98 out of 5 average rating, 174 reviews

The Guesthouse on Lime

A hidden treasure in the heart of the city. The space has a modern feel in a historic setting. Built in 1897, the building was first purposed as a tavern, and then housed several businesses through the years. In the 1980s, the building was renovated and transformed into two living spaces. This space is the first level, The Penthouse On Lime is the top level and is also available for rent. Original hardwood floors and high ceilings add to the charm of this gorgeous urban space.

A vintage living space features ornate floral wallpaper and rich, dark drapes. An elegant sofa and armchair provide seating, while a round dining table is adorned with a decorative bowl at its center. Golden light fixtures illuminate the area, enhancing the historic charm.

4.97 out of 5 average rating, 237 reviews

The Prohibition - Downtown Speakeasy with Hot Tub

Welcome Flappers and Gents to 1928 the height of the Roaring 20's! The Prohibition is a historic Victorian home in the heart of Downtown Lexington, walkable to everything! Your stay will transport you to the greatest time and party in history! Victorian and Art-Deco Antiques and Décor Flapper and Gent Cloths for Photos Hidden Speak Easy Bed Room Bourbon Mixing Bar (No Alcohol) Private Hot tub Scavenger Hunt Bicycles Private Parking and Entrance So much more!

A spacious living area features exposed brick walls and a stylish combination of furnishings. A plush blue sofa is positioned alongside an armchair, with a glass coffee table at center. Large windows provide natural light and views of the surrounding downtown scenery.

5.0 out of 5 average rating, 126 reviews

The Horse on High Knoll - DOWNTOWN Lexington!

Experience The Horse on High Knoll where historic Lexington charm meets modern comfort. Located in the heart of downtown, this unique stay features exposed brick, stylish finishes, and all the amenities you need for the perfect getaway. Walk to Lexington’s best restaurants, bars, coffee shops, and nightlife while enjoying the energy of the city. Whether you’re in town for Keeneland, bourbon, UK sports, or a weekend escape, you’ll be right in the middle of it all.

Superhost

A spacious living area features a blue sofa, a decorative wall art of an elephant, and a small dining table with two chairs. Natural light illuminates the room through several recessed lights, highlighting the warm wood flooring.

4.9 out of 5 average rating, 301 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.