Holiday rentals with a fireplace near Rupp Arena

4.93 out of 5 average rating, 184 reviews

Farm stay in Winchester

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the KY Horse Park and downtown Lexington. 30min to Keeneland. 45min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, fooseball and butlers pantry w/ coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

A view from a kayak on the water reveals a cabin nestled among trees on a grassy hillside. The sunlight filters through the leaves, casting soft shadows. The gentle ripples of the water reflect the surrounding greenery.

4.95 out of 5 average rating, 391 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

*Fiberoptic wi-fi added 10/11/22*Gorgeous N. Elkhorn Creek views from every room in this 1200 ft cabin on a private, gated horse farm. Your only neighbors are friendly horses! Wi/fi, SatTV/Netflix or enjoy wildlife viewing on the screened porch. Big Green Egg for grilling on the spacious deck. Fire pit and zipline. Living room/bedroom dual wood burning fireplace for chilly nights. Fully stocked granite kitchen. Kayaks available. Minutes to the Legacy Trail. 15 min to downtown Lex/G’town.

Superhost

The exterior of the cabin is showcased, featuring traditional log construction and a vibrant wooden door. A window with a flower box adds color, while the stone foundation provides structural support. Sunlight illuminates the rustic textures, highlighting the historical character of the building.

4.9 out of 5 average rating, 158 reviews

Historic and elegant Morrison Cabin built in 1787

The 1787 Morrison Log Cabin is located in the Gratz Park Historic District in Downtown Lexington & is the oldest house in Lexington on its original site. It’s a short walk to wedding venues,historic sites,the Convention Center,Opera House,Rupp Arena & the best dining and nightlife Lexington has to offer. Convenient to the Horse Park. The house is great for couples, business travelers & families.The completely renovated 1805 Thomas January Hemp House located next door is also available to rent.

4.93 out of 5 average rating, 202 reviews

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

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.

A bright and airy kitchen and dining area features a round table surrounded by four chairs, accented by greenery on the walls. A spacious countertop holds seating for two, complemented by modern appliances and a large window showcasing views of the outdoors.

4.99 out of 5 average rating, 144 reviews

Newly renovated upscale house with high ceilings

Get away and cozy in at this clean and comfortable two bed, two bath private home centrally located in a convenient, quiet neighborhood less than a five-minute walk to Kroger, restaurants, coffee, and a yoga studio. Easily accessible to Fayette Mall and UK by car. Fully equipped kitchen for cooking meals, reclining sofa for relaxing, 65" TV, books and games. One new Sealy king bed and a bunk bed with one double and two twin mattresses (one trundle). Washer and dryer available for your use.

4.99 out of 5 average rating, 138 reviews

Home in Georgetown

Hot Tub Glow Hill Home Near Horse Park and Ark

✨ Glow Hill — fun 2BR stay near downtown Georgetown 🛏️ 1 queen bed + flexible sleeping options: queen air mattress, twin futon chair & oversized 7ft lounge bean bag 🎮 Arcade games + game console for nights in 🛁 Private patio with gazebo, inflatable hot tub & LED glow ⚡ Fast Wi-Fi, workspace, full kitchen, washer/dryer 🔥 Fire pit, fully fenced yard, easy self check-in, free parking 👶 Family friendly with Pack n Play, baby bath & toys 🚗 13 min to Horse Park • 30 min to Ark Encounter

4.96 out of 5 average rating, 105 reviews

The exterior of a two-story duplex is showcased, featuring tall columns and a welcoming front porch. Lush green grass surrounds the building, complemented by trees and shrubbery. A flag hangs prominently from the porch, and a red vehicle is visible nearby.

Apartment in Lexington

Location Location Location-#15015318-1

Conveniently located across the street from Baptist Health hospital, and down the street from UK, this large 2 bedroom duplex is centrally located to all of Lexington. A 10 minute walk to Kroger Stadium. A 5 minute drive to downtown and a 10 minute drive to Keeneland. The city ordinance states, “The maximum number of occupants of this Short-Term Rental cannot exceed 4 people”. “Guests are prohibited from allowing more individuals than the maximum occupancy allows”, which is 6. Thanks!

The exterior of the condo features a two-car garage with a red vehicle parked in the driveway. A brick facade complements the structure, with large windows and a light entry door visible. A well-maintained lawn lies in front of the building.

4.99 out of 5 average rating, 114 reviews

HORSES, WILDCATS & BOURBON

3 bedroom/2.5 bath, 1900 sq ft condo less than 1 mile from I75 and 2 minutes from Griffin Gate Golf Course! Only 10 minutes from downtown, 10 minutes from Keeneland, 10 minutes from the KY Horse Park & 10 Minutes from UK!! 2 Car Garage. Great room features a floor to ceiling slate wall with built in electric fireplace. Kitchen features all NEW appliances & a breakfast bar. Large dining area easily seats 8. Wi-fi & Amazon Alexa! Licensed & Approved by City of Lexington.

The exterior of a ranch-style home is showcased, featuring a brick facade, a central entrance with a decorative door, and well-maintained landscaping. Two neatly trimmed shrubs flank the entrance, and a path made of bricks leads to the front door, set against a backdrop of green lawn.

4.95 out of 5 average rating, 114 reviews

Chevy Chase-RUPP/Kroger Field-Pet friendly w/fence

You will love this centrally located 3 bedroom, 2 bathroom home in the Chevy Chase area. Your pets will love our fenced in 'dog park' in the back yard. (This is a shared space with the apartment tenants next door) Our house is: - 1 walking mile to RUPP arena, downtown, The University of Kentucky Campus, Marriott City Center. - 3 minute WALK to Woodland Park. - 1.5 mile drive to Kroger Field - Just a short 8 mile drive to Keeneland, and 9.8 mile drive to the Horse Park.

4.94 out of 5 average rating, 580 reviews

A charming cottage exterior features a light grey facade with wooden accents. Two large black-framed doors open to a welcoming garden path, surrounded by lush greenery and blooming flowers. Planters with vibrant plants adorn either side of the entrance, complemented by decorative lanterns.

Guesthouse in Lexington

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

Superhost

The charming exterior of the house features a welcoming front porch supported by black columns. Two seating areas are visible on the porch, alongside plants and colorful hanging decorations. Lush green grass and landscaped shrubs frame the pathway leading to the entrance.

4.88 out of 5 average rating, 220 reviews

Luxe Home Downtown - Sleeps 6. Off-street parking

This dreamy getaway is located in the heart of Lexington's NoLi district where you can walk to breweries, boutiques & restaurants. Enjoy luxurious bedding & modern amenities while relaxing with family & friends. Our chef's kitchen features stainless cookware, quartz countertops & a granite island. Guests will enjoy our hi-speed wifi, a 55" smart TV in the living room & 43" smart TVs in each bedroom for streaming your favorite apps. Check-in easily w/ keyless entry.