Places to stay near Rupp Arena

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Top-rated vacation rentals near Rupp Arena

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The spacious home is set against a clear blue sky, featuring a combination of dark wood siding and a brown roof. A large deck is visible at the rear, while the surrounding green lawn creates a serene outdoor setting.

Chalet in Wilmore

4.91 out of 5 average rating, 137 reviews

Timberframe on Farm Lexington, KY Solar Power

Our home and farm is very secluded and overlooks the KY River situated on the top of the Palisades. Minutes from Lexington, Keeneland, Shaker Village, Bluegrass Airport and the Bourbon Trail 5 bedrooms, vaulted ceilings, a 3000 SF home with screened porch and a hot tub. We have a good layout for wheelchairs and a portable wheelchair ramp if needed. Fire Pit, hot tub and hiking trails available. We use solar power for our energy needs! Our pond has no fish but we can direct u to a place to fish!

Superhost

A spacious dining area is highlighted by a large wooden table surrounded by upholstered chairs. A chandelier hangs above, providing soft lighting. The adjacent living area features a comfortable sofa and large windows, allowing natural light to fill the space.

Home in Lexington

4.87 out of 5 average rating, 107 reviews

Great Location | Patio | Grill | Tempurpedic Beds

This beautifully decorated 2 bedroom and 1 bathroom home is the perfect getaway for a small group looking to explore Lexington. You'll be able to enjoy all Lexington's attractions without having too much trouble getting where you need go! This home is centrally located in one of the most desirable family friendly areas. This home is the perfect place for you to relax after an exhausting day. The professionally decorated interior will make sure everyones taste is satisfied, and with its elegant

Top guest favorite

A spacious backyard features a fire pit surrounded by three turquoise Adirondack chairs. Tall green grass covers the area, while a wooden privacy fence encloses the space. Mature trees provide shade and greenery, creating a peaceful outdoor setting.

Cottage in Lexington

4.93 out of 5 average rating, 155 reviews

Retro Mid-Century English Cottage

Just minutes to Keeneland and Red Mile. You’ll be glad you found this hidden gem in the Horse Capital of the World. Close to everything but in a safe and friendly neighborhood. Within ten minutes (or less) to Keeneland, Downtown, Rupp Arena, The Distillery District, UK, Masterson Station Park, Legacy Trail, The Arboretum or a scenic drive down Old Frankfort Pike. Our cozy cottage boasts two bedrooms with queen beds, a huge back yard with privacy fence to relax in, wi-fi, and large screen tv.

Top guest favorite

A brick pathway leads to a charming cottage with a black front door and dark shutters. The cottage is framed by lush greenery, creating an inviting entrance. Sunlight filters through the trees, illuminating the pathway and surrounding landscape.

Guesthouse in Nicholasville

4.98 out of 5 average rating, 339 reviews

Cottage Retreat - Wine, Horses, Convenient

Just south of Lexington KY. Cottage Retreat - nestled between horse farms & open land this 25 acre farm is a unique & convenient location to relax and spend time unwinding. 7.8 miles from the Bluegrass Airport, 10.8 miles from Rupp Arena, 8.4 miles from Keeneland - you're close to numerous items of interest. Enjoy the fully remodeled private cottage, stroll down the lane, enjoy the close proximity of horses, and perhaps buy a bottle of wine on site. No pets and no smoking. Thank you.

Guest favorite

A welcoming living area features a light gray sofa adorned with patterned cushions. A round pink coffee table is centrally placed, holding a tray of magazines. Natural light enters through large windows, illuminating the space, while a ceiling fan enhances airflow.

Home in Lexington

4.94 out of 5 average rating, 729 reviews

Adorable, Clean Lexington Cottage, Convenient to Everything

You'll love this bright, well-decorated home away from home! Located in an OPTIMAL location for all that Lexington and surrounding areas have to offer. Safe neighborhood. Xtra long driveway. Comfy beds. Fully fenced in backyard and large patio-NEW PHOTOS COMING SOON! *IF YOU HAVE MORE THAN 2 PETS, YOU MUST CONFIRM WITH ME BEFORE BOOKING. $40 P/PET FEE BEYOND 2. TOTAL # OF PETS ALLOWED DEPENDS ON TYPE/SIZE. YOU ARE RESPONSIBLE FOR ANY DAMAGE/STAINS TO BEDDING, FURNITURE, LANDSCAPING, ETC...

Top guest favorite

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

4.95 out of 5 average rating, 173 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Superhost

The entrance features a bright red door framed by two large flower pots filled with vibrant flowers. A clean pathway leads from the door to the sidewalk, and the facade is complemented by gray siding and wooden support beams.

Apartment in Lexington

4.9 out of 5 average rating, 98 reviews

Hidden Gem|One Bedroom Apt Downtown Lexington

Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.

Top guest favorite

Apartment in Lexington

5 out of 5 average rating, 116 reviews

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.

Guest favorite

The charming exterior of the cottage is highlighted by two symmetrical windows and a central door framed with dark wood. Lush greenery properties a potted plant atop a rustic barrel and vibrant flowers adorn the window boxes, enhancing the inviting entrance.

Guesthouse in Lexington

4.94 out of 5 average rating, 511 reviews

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

Top guest favorite

A spacious living room features modern furnishings with a blue sofa and a brown armchair, creating a cozy atmosphere. Natural light illuminates the room, highlighting the decorative fireplace and mounted TV above it. A kitchen and dining area are visible in the background.

Home in Lexington

4.98 out of 5 average rating, 101 reviews

Bluegrass Retreat with Hot Tub! Near Horse Park!

Unbeatable location for the best experiences in Central Kentucky! You will be close to the Kentucky Horse Park, historic Keeneland, downtown Midway, the Ark Encounter, Rupp Arena and downtown Lexington, UK sporting events, golf courses, and several highly desirable distilleries including our personal favorite - Buffalo Trace Distillery. There are so many great restaurants nearby! Be sure to check out our Guidebook when you book a stay at Bluegrass Retreat.

Guest favorite

A wooden railing overlooks a serene river, with trees lining the opposite bank. A cozy plaid blanket drapes over the railing, alongside a glass decanter and two glasses, capturing the golden hues of a sunset.

Apartment in Winchester

4.89 out of 5 average rating, 148 reviews

The River House Floor 2 Getaway, w/a river view.

Enjoy the spectacular views of the Kentucky River from this second floor studio. Located within an easy walk of hiking trails. After your hike (or whenever, you are on vacation), visit the Waterfront Grill or Hall’s on the River. They offer dining, bar, and seasonal outdoor seating. They are about a half mile down the road from the cottage. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby.

Guest favorite

An open kitchen features warm wood cabinetry and granite countertops. Three metal bar stools are positioned at a central island. Stainless steel appliances and modern lighting contribute to a functional space connecting to the living area, with wooden accents enhancing the design.

Apartment in Lexington

4.94 out of 5 average rating, 159 reviews

New! One Bedroom Apt - Close to Everything

This apartment is the perfect location for catching a UK game, a weekend at Keeneland, business trips or clinical rotations. It features an open concept kitchen and living area. The bedroom connects to a master bath with beautiful counter tops and fixtures. Simply pull the barn doors shut for privacy from the living area. Also features new stainless steel appliances, granite countertops, cultured marble shower, washer/dryer, and convenient parking.