Places to stay near Rupp Arena

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.

4.93 out of 5 average rating, 935 reviews

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

ValueFamilyWalkability

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.

ValueFamilyCleanliness

The Victorian home is illuminated at dusk, showcasing intricate architectural details. The facade features bright red brick and stone accents, complemented by a decorative arched entryway and porch. Windows with warm light hint at the inviting atmosphere within.

4.82 out of 5 average rating, 301 reviews

Arcadium Downtown KING BED / Free Late checkout

Located in a Victorian home this apartment is perfect for a trip into Lexington! Located just a block away from the Central Bank Center, the location is great. The beds are comfortable and the space is great for a night in or a quick walk downtown. We are located just minutes from Keeneland. UPDATE: Just added a 4player Arcade Emulator machine, with up to 5,000 games to keep you entertained. This custom arcade is a gamer’s dream, featuring thousands of console games and classic arcade games.

LocationValueCheck-in

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.

4.96 out of 5 average rating, 150 reviews

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!

LocationFamilyAir conditioning

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.

4.94 out of 5 average rating, 269 reviews

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

FamilyLocationNearby

4.89 out of 5 average rating, 272 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**

LocationValueIndoor spaces

A comfortable living area features a gray sectional sofa adorned with green and white cushions. A round coffee table sits at its center, topped with a vase of flowers. Soft lighting is provided by a chandelier above, and a television is mounted on a textured wall.

4.98 out of 5 average rating, 183 reviews

Historic Mansion in Heart of Downtown Lexington!

Located in the heart of historic downtown Lexington, the home combines original craftsmen woodwork from 1902, yet modern amenities to provide an upscale stay. Fully remodeled in 2018, the home is walking distance to Rupp Arena, both the University of Kentucky and Transylvania University's campuses, fine dining at Jeff Ruby's, Tony's, Frank & Dino's and many others, as well as event spaces at the Limestone Hall, the Grand Reserve, and the newly completed Lexington Convention Center!

ValueLocationTV

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.

FamilyValueComfort

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, 238 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!

ValueFamilyIndoor spaces

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, 127 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.

FamilyLocationSleep quality

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.

LocationValueAccess

4.9 out of 5 average rating, 198 reviews

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon

Historic charm w/ modern comforts in this immaculate downtown first floor flat. Positioned at the entrance to Town Brach Distillery, this beautiful home is walkable to incredible restaurants and bars downtown Lexington - Don’t park in the front of the house, they will issue a ticket. * Rupp Arena 0.5 miles * Keeneland Racetrack 5.5 miles * Kentucky Horse Park 8 miles * STR Reg #15062369-2 - Maximum occupants 4

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Popular amenities for vacation rentals near Rupp Arena

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Condo rentals with wifi

4.92 out of 5 average rating, 176 reviews

Graffiti Art Haus - Walk to Central Bank Arena

LocationFamilyCheck-in

4.96 out of 5 average rating, 261 reviews

The FLAT at Bell Place - Downtown/Horse Park

LocationFamilyView

A modern living area features a comfortable gray sofa with colorful accent pillows, complemented by an elegant coffee table. An artistic mural adorns the wall behind, creating a vibrant focal point. Ambient lighting is provided by stylish floor lamps, enhancing the contemporary decor.

4.86 out of 5 average rating, 284 reviews

Lexington's Artistic Bunker / 1BR Downtown Condo

FamilyLocationParks

A playful artwork of a panda wearing colorful glasses, showcasing vibrant and textured brush strokes. The panda's joyful expression is highlighted with round, twinkling eyes, surrounded by a mix of colors that enhance its charming features. The background remains neutral, allowing the panda to stand out.

4.94 out of 5 average rating, 202 reviews

Across From UK Hospital-Weekly/Monthly Discounts!

LocationValueNearby

The bedroom features a spacious bed with a decorative bedspread, flanked by two bedside tables topped with lamps. Light grey walls and soft carpeting create a calming environment, while decorative wall elements enhance the overall appeal.

4.92 out of 5 average rating, 184 reviews

*Private Apartment with Balcony | W/D inside apt*

ValueLocationDecor

The bedroom features a spacious bed dressed in white linens, accented by vibrant green pillows. Tall green curtains frame two windows, allowing natural light to enhance the room. A large artwork adorns the wall above the bed, while a plush bench sits at the foot of the bed.

4.98 out of 5 average rating, 169 reviews

Keenland Special- 2 Mi. to Downtown - Rupp - UK

LocationValueBackyard

4.95 out of 5 average rating, 107 reviews

The exterior of the Paradise Inn B&B showcases a charming three-story building with a vibrant yellow and red brick façade. Large windows are framed in white, allowing natural light to illuminate the interior. A sign for Paradise Cafe is prominently displayed at the entrance.

Condo in Paris

Paradise Inn B&B - Honeymoon Suite

FamilyLocationKitchen

5.0 out of 5 average rating, 17 reviews

Thoroughbred Retreat Unit 803

LocationCleanlinessParking

Family-friendly house rentals

4.98 out of 5 average rating, 514 reviews

Distillery District Diamond-pet friendly

LocationFamilyAir conditioning

A welcoming front porch features a solid door with an address number visible. A small, potted evergreen plant stands next to the door. A black chair with a red cushion is positioned nearby, alongside a geometric decorative table. The porch floor is finished in dark wood.

4.93 out of 5 average rating, 471 reviews

Big Rock Cottage

ValueLocationHeating

An inviting exterior view showcases a modern building at dusk, featuring warm light from hanging fixtures. A raised planter with vibrant greenery adorns the front, complemented by a wooden railing along the entrance, with a paved sidewalk lined by trees.

4.88 out of 5 average rating, 324 reviews

IT WAS ALL A DREAM - Modern Luxury in downtown LEX

LocationFamilyKitchen

A bright living space features two sofas, one in teal and one in cream, accompanied by a wooden coffee table. Artwork adorns the walls above a decorative fireplace. A large television is positioned in the corner, while natural light streams through the windows, enhancing the welcoming atmosphere.

4.89 out of 5 average rating, 135 reviews

Historic West Second Downtown Home

ValueFamilyLayout

4.85 out of 5 average rating, 124 reviews

Home in Chevy Chase

*Chevy Chase TH (1) mile to UK | EV Charging*

FamilyLocationPets

The kitchen features white cabinetry contrasted against vibrant green walls. A spacious countertop is equipped with modern appliances, including a gas stove and microwave. Natural light is provided by a large window, complemented by a dining area with minimalist seating.

4.92 out of 5 average rating, 265 reviews

My Old Kentucky Home

ValueLocationHeating

4.95 out of 5 average rating, 249 reviews

A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.

Home in Versailles

Quaint little farm house close to Keeneland/horses

LocationValueCleanliness

A cozy sitting area features exposed wooden beams and a decorative fireplace. Colorful armchairs are arranged around a central table, with a large flat-screen TV mounted on the wall. Natural light filters through the windows, enhancing the elegance of the space.

4.89 out of 5 average rating, 168 reviews

Historic and elegant Morrison Cabin built in 1787

ValueLocationAir conditioning

Apartment rentals with air conditioning

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

FamilyValueKitchen

4.96 out of 5 average rating, 113 reviews

Witchy Boutique Studio in 1890s Saloon Downtown

FamilyLocationBathroom

An aerial view captures a two-story house with a dark roof and a white exterior, positioned next to a well-maintained lawn. A concrete driveway leads to the entrance, with paths of grass lining the edges. Surrounding buildings and greenery are also visible.

4.92 out of 5 average rating, 129 reviews

Victorian Apt Downtown Lexington

FamilyLocationOutdoor spaces

A spacious bedroom features a king bed with a light-colored coverlet against a backdrop of eclectic wall decor and built-in shelving. Textured rugs cover the hardwood floor, while large windows with patterned drapes allow natural light to fill the room, creating a cozy atmosphere.

4.98 out of 5 average rating, 648 reviews

Haven on High Street Private Apt Historic Home

ValueLocationLaundry

A spacious living area is highlighted by a light-colored sofa adorned with decorative pillows. Artwork featuring playful horse designs decorates the gray walls. A glass coffee table sits atop a patterned rug, and a TV is positioned on a white media console, creating a cozy atmosphere.

5.0 out of 5 average rating, 116 reviews

Downtown 2BR | Walk to Rupp · Porch · Parking

ValueLocationCheckout

A cozy living area features a brown sofa with a textured blanket, positioned near a circular coffee table set with glassware. Exposed brick walls and wood beams add character, while a subtle lighting fixture highlights the space. An antique painting adorns the wall beside a decorative fireplace.

4.96 out of 5 average rating, 341 reviews

Cozy Private Upstairs Loft in Historic DT Home

LocationValueDecor

A welcoming living area features a warm beige sofa adjacent to a wooden coffee table. Large windows allow natural light to fill the space. Decorative artwork hangs on the walls, and a tall floor lamp adds soft illumination. A vibrant area rug complements the overall decor.

4.9 out of 5 average rating, 431 reviews

Trendy 2 bedroom in the Distillery District

LocationFamilyComfort

The exterior of a two-story brick building is displayed, featuring a welcoming porch with white railings. Lush green trees frame the entrance, and a path leads to the front door. The property exhibits a blend of classic architecture and natural surroundings.

4.95 out of 5 average rating, 260 reviews

Canopy of trees

LocationValueHospitality

Other great vacation rentals near Rupp Arena

4.86 out of 5 average rating, 272 reviews

A welcoming chalkboard wall displays a map of Bourbon attractions and a list of local distilleries, breweries, and restaurants. A modern kitchen area is visible, featuring wooden countertops and bar stools, while the living room beyond offers a comfortable seating arrangement and a serene atmosphere.

Townhouse in Lexington

*Bourbon, Bourbon, Bourbon*

ValueLocationOutdoor spaces

4.9 out of 5 average rating, 409 reviews

Bungalow in Lexington

BoHo Paradise - Fire Pit- Downtown - Rupp Arena

LocationFamilyAmenities

A well-lit room features a spacious bed dressed in crisp linens, accented by decorative pillows. A large flat-screen TV is mounted on the wall, above a stylish fireplace. Two cozy armchairs are positioned around a coffee table, with window views framed by curtains.

4.96 out of 5 average rating, 50 reviews

Stylish Downtown Apt in Historic Bldg | Walk2Rupp

FamilyLocationSleep quality

4.99 out of 5 average rating, 86 reviews

Ralph Lauren Inspired, Walk to Rupp Arena, Parking

FamilyValueHospitality

An updated kitchen showcases stainless steel appliances and quartz countertops, complemented by blue cabinetry. A central island includes a gas cooktop. A dining area is featured, equipped with a table that seats six. Natural light floods the space through multiple windows.

4.9 out of 5 average rating, 82 reviews

Walk to Rupp Arena/3Bedroom/Parking

LocationFamilyAmenities

A well-lit bedroom features a spacious bed with decorative pillows, complemented by a cozy seating area with two armchairs. Exposed wooden beams provide character to the ceiling, and shelves are visible in the background, enhancing the open feel of the space.

4.64 out of 5 average rating, 36 reviews

Sleep-easy Lex steps to restaurants and Rupp Arena

LocationValueCheck-in

4.98 out of 5 average rating, 61 reviews

Modern Townhouse Near Rupp and Distillery District

ValueLocationKitchen