
Places to stay near Rupp Arena
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Top-rated vacation rentals near Rupp Arena
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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

Man O'War @ The HoM- KY Horse Park, Ark, Historic
Welcome to Man O War! A 1500 sq ft luxury 1st floor condo located inside the Historic House on Main. This 2-bedroom, 2 bath condo offers a perfect blend of modern luxury & style coupled with the elegant charm of a Historic Kentucky home. Originally built in 1872, The House on Main functions as a charming boutique hotel property with 4 units: Secretariat - 1st floor 2bed/2ba Man O’ War - 1st floor 2bed/2ba Sir Barton - 2nd floor 1bed/1ba (w/sleeper) War Admiral - 2nd floor 1bed/1ba (w/sleeper)

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.

Graffiti Art Haus - Walk to Central Bank Arena
Industrial art haus just 3 blocks to Rupp Arena, a short walk to Gatton Park & only one block from Jefferson Street, with lots of dining & drinking options! Less than 1 mile to the Distillery District. Our guests will enjoy covered parking, luxury bedding, 2 smart TVs, a well-stocked kitchen & commercial laundry with sleeping arrangements for 4 people (1 king bed & 1 sofa bed). Whether you're in town for a concert, Keeneland, a wedding, graduation or work - this art haus is the ideal getaway!

1st Boarding House Lexington / Free Late Checkout
Welcome to Lexington’s oldest boarding house. Built in 1880 this massive landmark was constructed into rooms to accommodate train travelers. The property is found in the historic Woodward Heights, one block away from Rupp Arena and Lexington Center. Also, adjacent to the Lexington Brewing and Distilling Co. You can walk .5 miles the to downtown attractions or the distillery district. The home has been in our family for almost 40 years and, we are excited to welcome travelers, once again.

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**

My Old Kentucky Home-Downtown LEX's Premier Stay!
Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

LUXURY Downtown Retreat 💙 w/ King Tempur-Pedic Bed
Welcome to your Kentucky Home This beautifully remodeled historic property is located in Downtown Lexington. Walk to Rupp Arena, several cool bars/breweries and upscale restaurants. King Tempur-pedic mattress with sleeper sofa. 2 smart TV's and high speed internet service. Beautiful kitchen with gas range and stainless steel appliances. * Rupp Arena - 1 mile * Keeneland Racetrack - 7 miles * Kentucky Horse Park - 8 miles * STR Reg #15062369-5 - Maximum occupants 4

Swanky Boho - Downtown
Discover a trendy and stylish bohemian-inspired oasis. Immerse yourself in the vibrant and artistic ambiance, perfect for a memorable stay. Relax amidst eclectic decor, embrace the laid-back bohemian lifestyle, and indulge in the inviting atmosphere. With modern amenities and a prime downtown location near hip cafes, coffee shops, and nightlife, this is the ultimate choice for those seeking the boho-chic vibe. Unforgettable memories await in this captivating retreat.

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.

Big Rock Cottage
Charming Cottage located in Downtown Lexington. Completely remodeled - clean and pristine. Two bedrooms and two full baths. Fully equipped kitchen, Waher / Dryer and large back porch. Only 1/2 a block away from Legacy Trail and walking distance to Rupp arena and all downtown activities. Please note that this is located downtown you will see diversity both in culture and socio-economic status. :1506321-1:

*One Bed Apartment|One Mile to Rupp Arena*
Our brand-new 1-bedroom apartment is conveniently located near University of Kentucky, Transylvania, National Avenue Warehouse District, The Legacy Trail, Restaurants, fine dining & nightlife. Walkable to nearby yoga studios, Historic Lyric Theatre, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Martine's Pastries next door is a perfect spot for coffee and pastries. Approximately, 5 miles from I75\64.
Popular amenities for vacation rentals near Rupp Arena
Condo rentals with wifi

Boho Bungalow

*Bluegrass Getaway*

Lexington's Artistic Bunker / 1BR Downtown Condo

Thoroughbred Retreat Unit 803

The FLAT at Bell Place - Downtown/Horse Park

Top Shelf the only Airbnb in KY above a Distillery

Paradise Inn B&B - Lover's Suite

Private Condo Downtown, Walk to Rupp Arena
Family-friendly house rentals

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

KY & Bourbon & Horses, Oh My! Close to Keeneland

Distillery District Diamond-pet friendly

Maryland Luxury Downtown Manor

Quaint little farm house close to Keeneland/horses

Cottage w/Jacuzzi - centrally located, comfy beds!

Cozy 1-bedroom in Lexington

Quaint cottage on scenic horse farm
Apartment rentals with air conditioning

Canopy of trees

Downtown Digs-Spacious Loft

The Guesthouse on Lime

Cozy Broadway Apartment

The Blue House and Gardens: Unit 2

Charming Downtown Apartment in Georgetown, KY

Victorian Apt Downtown Lexington

A Little Piece of Versailles
Other great vacation rentals near Rupp Arena

Walk to Rupp Arena/3Bedroom/Parking

Sleep-easy Lex steps to restaurants and Rupp Arena

Downtown 2BR | Walk to Rupp · Porch · Parking

BoHo Paradise - Fire Pit- Downtown - Rupp Arena

Lexington Manor

Carriage House

Absolutely perfect downtown location

Lovely Private Suite • Walk to Rupp • Free Parking
Destinations to explore
- Ark Encounter
- Kentucky Horse Park
- Buffalo Trace Distillery
- University of Kentucky
- Castle & Key Distillery
- Four Roses Distillery Llc
- The Arboretum, State Botanical Garden of Kentucky
- Raven Run Nature Sanctuary
- Shaker Village of Pleasant Hill
- McConnell Springs Park
- Old Fort Harrod State Park
- Talon Winery & Vineyards
- Lovers Leap Vineyards and Winer
- Cove Spring Park
- Equus Run Vineyards
- Kroger Field
- Masterson Station Park
- Fort Boonesborough State Park





