Holiday houses in Lexington

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Top-rated holiday rentals in Lexington

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Guest favourite

Train in Lawrenceburg

4.99 out of 5 average rating, 337 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of elm trees on a working cattle farm, The Southern x525 Caboose is now resting in the heart of the Bourbon Trail. Maintaining the industrial feel of an authentic caboose, while bringing in the warmth of handcrafted woodwork design, the Caboose on the Farm creates a unique experience like no other! Queen bed, twin bunk-beds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Guest favourite

Home in Lexington

4.93 out of 5 average rating, 702 reviews

Restored historic Lex charm!Walk to Rupp/dining/UK

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!

Guest favourite

Cottage in Lexington

4.94 out of 5 average rating, 696 reviews

Little House Dwntwn - Close to Rupp & Restaurants

1 BR, 1 bath, restored house on quiet street in downtown. Patio (with umbrella), & front porch - each with table & chairs, Off-street parking, TV in Living Room and in Bedroom, Broadband Internet, Cntl A/C, Complete kitchen w/microwave, refrigerator - freezer, toaster oven, regular oven and stove, flatware, dishes and cooking utensils, dishwasher, and washer-dryer. 15 min. to Keeneland or Horse Park. 1.5 miles to UK. 1/2 mile to Rupp (10 minute walk.) Walk to many restaurants and attractions.

Guest favourite

Guesthouse in Nicholasville

4.98 out of 5 average rating, 317 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 favourite

Farm stay in Versailles

4.91 out of 5 average rating, 420 reviews

Bluegrass Country Cottage

Enjoy a quaint, private, quiet & charming little place to call your own, on a small, working (seasonal) Thoroughbred horse farm. Green acreage, lovely scenes and sunsets. Located in horse country, between historic Winstar Farm and Lane's End Farm, just a short drive to small town USA, Versailles; historic Midway; and to the nearby City of Lexington, home of the Kentucky Wildcats, Horse Capital of the World, Bourbon Country & so much more. Pets allowed (2 max), well behaved, pet fee applies.

Guest favourite

Townhouse in Lexington

4.89 out of 5 average rating, 430 reviews

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.

Guest favourite

Rental unit in Lexington

4.96 out of 5 average rating, 262 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!

Guest favourite

Rental unit in Lexington

4.98 out of 5 average rating, 537 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.

Guest favourite

Treehouse in Georgetown

4.93 out of 5 average rating, 166 reviews

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

Guest favourite

Serviced apartment in Lexington

4.91 out of 5 average rating, 177 reviews

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.

Superhost

Cabin in Lexington

4.82 out of 5 average rating, 511 reviews

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

Guest favourite

Rental unit in Lexington

4.92 out of 5 average rating, 145 reviews

10 minutes from Keeneland,airport, downtown and UK

Newly renovated 1 bedroom apartment with private bathroom and full kitchen with private entrance. Nestled in a quiet safe neighborhood on the south side of Lexington. Conveniently located 10 minutes from Keeneland, airport, downtown and University of Kentucky campus. King size bed, WiFi, and access to laundry are just some of the great amenities offered in this luxurious dwelling. Owner lives on site and is available for assistance at any time.