Holiday rentals with a fireplace near Rupp Arena

A private entrance is framed by trees displaying vibrant autumn foliage, adding bursts of red and orange. A gravel driveway leads toward a gated entrance, while fallen leaves create a colorful carpet along the pathway. Clear blue skies provide a bright backdrop.

4.95 out of 5 average rating, 381 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

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.

4.91 out of 5 average rating, 156 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, 191 reviews

A charming cottage is surrounded by a manicured lawn and mature trees, showcasing a brick exterior and a circular front path leading to the entrance. Nearby houses reflect uniqueness, contributing to the friendly neighborhood atmosphere.

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.

The living room features vaulted ceilings and an open layout. A sectional sofa and a reclining chair offer comfortable seating, while a coffee table sits centrally. Light hardwood flooring and soft wall decor contribute to a bright and airy ambiance. A large TV is mounted on a nearby wall.

4.99 out of 5 average rating, 134 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.

4.89 out of 5 average rating, 114 reviews

A spacious living room featuring a light-colored sectional sofa with ample seating, complemented by a dark wood coffee table. Large windows allow natural light to fill the space, framed by navy blue curtains. A ceiling fan enhances airflow in this modern area.

Apartment in Lexington

Penthouse @ 175 LEX -Walk to Rupp Arena on Main St

Offering unparalleled 270-degree views of Downtown Lexington on Main Street with a private balcony! The Penthouse is newly constructed featuring a full kitchen with quartz countertops & breakfast bar, dining table, balcony, 3 bedrooms each with queen-sized beds, two bathrooms, full living room with two sleeper sofas and private washer/dryer. Located in the heart of Lexington, walkable to Rupp Arena, Keeneland and Carson's, there isn't a more convenient spot to stay close to the action!

The kitchen showcases wooden cabinetry extending to the ceiling, paired with a dark granite countertop. Stainless steel appliances, including a microwave and oven, are featured. The backsplash is adorned with a mosaic pattern, and ample lighting illuminates the space from recessed ceiling fixtures.

4.99 out of 5 average rating, 111 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.

A spacious bedroom features a large bed with neutral-toned bedding, flanked by two wooden nightstands with table lamps. Natural light filters through two windows, and an abstract painting is displayed above the bed, adding a touch of color to the serene space.

4.93 out of 5 average rating, 200 reviews

Bright Cozy Stay| Fenced Yard| Near I-75 Horsepark

The Kearney: newly renovated home in the beautiful 'Kearney Hall' neighborhood, primely located off the 64/75 intersection. This home is a perfect 'trifecta' between Lexington, Louisville, & Cincinnati! Situated only 8 minutes from the KY Horse Park, 15 minutes from Downtown Lexington and Keeneland Racecourse. This quaint home blends cozy with natural, modern elements for a pleasant stay. Bring your crew to experience a day at the tracks, a bourbon tour, or a KY family getaway!

The exterior of the home features natural stone accents, complemented by brown shutters on the windows. A well-maintained lawn with shrubs and seasonal foliage enhances the inviting entry. A concrete driveway provides parking, while a wooden deck is visible at the side of the house.

4.99 out of 5 average rating, 120 reviews

Creekside cabin in city. King bed. Walk in shower

Unwind in the perfect fusion of City convenience with Nature Vibes. The backyard is privately lined with Native shrubs, Creek and abundant hardwoods. Listen to the birds while enjoying your morning coffee on the spacious deck. Visit the prayer garden in the back of the property or swing next to the creek and fire pit. Shillito Park is within walking distance. The Bluegrass Airport, UK and Keeneland are approx 10 min. King bed and private bath in Master. TV in all rooms.

4.94 out of 5 average rating, 567 reviews

A polished copper bar counter reflects a variety of bourbon bottles and mixers. A cocktail shaker and glass sit ready for use, accompanied by a stylish ice bucket. The arrangement provides a glimpse into a well-equipped space for cocktail preparation.

Guest house 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

A bright and airy living space features a yellow sofa accented with colorful pillows, a cozy brown chair, and a round wooden coffee table. Natural light floods in through a large window with sheer curtains, illuminating the open layout that connects to a modern kitchen at the back.

4.87 out of 5 average rating, 213 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.

The living room showcases a combination of blue and brown sofas with colorful throw pillows, centered around a natural gas fireplace. A Smart TV is mounted above the mantel. Open space leads to a kitchen with a breakfast bar and dining area in the background.

4.98 out of 5 average rating, 130 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.