Holiday houses in Lexington

4.91 out of 5 average rating, 291 reviews

Bungalow in Lexington

Cozy BoHo Paradise - Downtown - Rupp Arena

Start your mornings with a fresh cup of coffee and unwind in the indoor hammock with your favorite book. This charming, bohemian-style cottage offers a cozy, fully furnished retreat right in the heart of Lexington’s lively Distillery District. Just 1.5 miles from Rupp Arena and 5 miles from Keeneland, perfectly positioned to explore the city's best. Surrounded by local cafés, great restaurants, and the buzz of downtown, this inviting hideaway is the ideal home base for your Lexington adventure.

4.93 out of 5 average rating, 773 reviews

Restored charm! Walk to Rupp. Easy Keeneland drive

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 or sporting event at nearby Rupp Arena (5 minute walk), watch the horse races at Keeneland (10 minute drive down the road), tour the bourbon distillery right around the corner, or explore the unique offerings of downtown Lexington. Stay in the heart of it all!

4.92 out of 5 average rating, 271 reviews

Trendy 2 bedroom in the Distillery District

This trendy two-bedroom apartment is located in Lexington’s coolest new spot, the Distillery District (Breweries, Restaurants, Bars, Pizza, Ice Cream, and Live Music). You can’t ask for a more convenient location… 2 blocks from The Burl 5-minute walk to the Distillery District Less than 1 mile to Manchester Music Hall 1.5 miles to Rupp Arena 2 miles to Downtown Lexington 20 minutes to Keeneland and the Airport We provide all the amenities you might need, including a fully supplied kitchen.

4.88 out of 5 average rating, 483 reviews

Townhouse in Lexington

Cozy, cute 2BR townhouse near downtown, businesses

Registration#15019537-1 Comfy, cozy Five Squared is tucked in a quiet neighborhood near downtown's restaurants, bars and arts; Rupp Arena and UK basketball games and concerts; the hip Distillery District's restaurants; and Meadowthorpe's antique shops. For business travelers, it's also convenient to New Circle Road and local industry. Our place is great for couples, solo travelers, families with kids, and anyone who likes cotton sheets, exposed brick and the gentle rumble of passing trains.

4.95 out of 5 average rating, 323 reviews

Enjoy Downtown Lex from your Private Deck

Walkable to downtown, Rupp/Convention Center, Town Branch Distillery & less than 1 mi to UK student center. 12 min drive to Keeneland, 19 min to horse park. Sleeps 2-3 with 1 queen size bed and a couch bed. Equipped with basic kitchen amenities, all new appliances, washer/dryer, 2 Smart TVs & WIFI. Bedroom features a glass garage door that opens to a private patio. This apartment is located in a brand new building with free parking on premises. Energy efficient, simple, center of it all!

4.98 out of 5 average rating, 573 reviews

Haven on High Street Private Apt Historic Home

Haven on High St. Quiet-gracious-comfy-one bedroom apartment in 1842 home. Off street parking. King bed in bedroom, comfy queen sofa bed in living room, claw foot tub. Eclectic decor-a visual artistic treat. By design, the space is not kid or pet friendly. Fully furnished kitchen+coffee, tea, snacks. Private apartment-shared courtyard. Walk to coffee shop, UK, Rupp, downtown dining. Beautifully landscaped gardens with patio and porch seating. Host lives next door and available-as needed.

4.98 out of 5 average rating, 484 reviews

Game of Thrones - Downtown

Be the lord or lady of this palatial chamber, in the center of downtown‘s hottest spots. Your OMG stay comes w/royal features inspired by your favorite fantasy series. •Custom Calif. King wooden bed w/playroom features and a mini-dungeon (not just for containing dragons!) •Luxurious bathroom w/steam shower for two •Decor from Old World Europe: hand-crafted torch sconces, medieval-style weaponry and an iron throne •Custom Coffee Bar w/touch-screen access to your favorite cafe coffees

4.97 out of 5 average rating, 367 reviews

Cabin in McKee

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

4.93 out of 5 average rating, 199 reviews

Guesthouse in Winchester

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

4.93 out of 5 average rating, 221 reviews

Treehouse in Georgetown

Treehouse with TWO outdoor tubs by the creek!

Welcome to your romantic treehouse getaway! Nestled among the trees, this one-bedroom treehouse is the perfect spot if you're looking for a unique & unforgettable experience. The treehouse features a large glass rolling garage door allowing stunning views of the sunset, but the highlight is undoubtedly the double tubs overlooking the creek. ✔ Queen Bed ✔ Outdoor Deck with Seating ✔ Double Outdoor Bathtubs ✔ Outdoor Shower ✔ Composting Toilet ✔ Creek Access ✔ Indoor Cooking Station

4.95 out of 5 average rating, 205 reviews

Canopy of trees

Enjoy this peaceful and centrally-located apartment. Across the street from the historic Henry Clay estate. Just a few miles from Rupp arena, Uk, stadium and downtown. A short drive to the horse park. Walking distance to restaurants. There is a $50 per pet fee. Please be sure to include pet in your booking. This is a one bedroom with a queen bed. The couch folds into a sleeper and there are curtains for privacy.. Street parking only. The back and driveway are our private areas

Superhost

4.9 out of 5 average rating, 112 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.

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Popular amenities for Lexington holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Lexington

4.92 out of 5 average rating, 151 reviews

Farm stay in Winchester

LenMar Farm Country Stay near Lexington KY

ElizabethRating, 5 stars1 week ago

Nice place to stay quiet and pretty! Didnt like the parking in front and walking around the back otherwise was great clean place!! Host was nice and responsive

4.98 out of 5 average rating, 119 reviews

The Guesthouse on Lime

DavidRating, 5 stars6 days ago

One of the best places I have rented. I walked back and forth through Tarp's space for over half an hour just taking it in when I first arrived. I'll be back.

4.94 out of 5 average rating, 137 reviews

Nonie's Abode

JeanneRating, 5 stars2 weeks ago

we had a relaxing and peaceful stay at Nora's place. The beds were very comfortable, great shower and spacious living space. also a beautiful deck and gardens outside! thank you!

4.97 out of 5 average rating, 159 reviews

Bungalow in Lexington

Cozy Kenwick Bungalow in the Heart of Lexington

AndreaRating, 5 stars2 weeks ago

Super cute house in a great location! The backyard was perfect for our dogs. It was large and completely enclosed. Host answered all of our questions and gave us a great recommendation for morning coffee!

4.82 out of 5 average rating, 576 reviews

Cabin in Lexington

Unique Stay - 1907 Log Cabin Near Kentucky River

RachelRating, 5 stars1 week ago

Laura’s place was perfect for our family of four. It was very quiet and peaceful, while still being located conveniently to everything we wanted to visit in Lexington. Laura was very responsive when we had issues with our arrival and came quickly to help us. We throughly enjoyed our stay and will happily stay again when we return to Lexington.

4.95 out of 5 average rating, 356 reviews

Horse Farm Creekside Cabin- 6 min to KY Horse Park

DavidRating, 5 stars3 weeks ago

Had a blast. The zip line was a hit for the girls. They loved feeding horses. It was a great get away. We definitely will stay here again the next time we are in Lexington.

4.88 out of 5 average rating, 136 reviews

El Retro- Mid Century Ranch near Horse Park & Rupp

TonyaRating, 5 stars4 days ago

Brayhan’s place was clean and neat. We needed last minute accommodations on a long road trip and we appreciate Brayhan accommodating. It was convenient to I-64 and had lots of great surrounding restaurants.