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Lexington vacation rentals

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Top-rated vacation rentals in Lexington

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

Guest favorite
Loft in Lexington
Spring Street Loft by Rupp-Covered Parking + Deck
Brand new 2nd-level loft with free covered parking spot beneath, a huge deck and outdoor dining option. Directly across Maxwell St. from Rupp Arena's parking lot-you can't get any closer! This single unit building was built on stilts to maximize outdoor space and downtown views. Your perfect oasis in the middle of the action includes a full kitchen, laundry room, bathroom, living area and Smart TV. Come for a concert or stay awhile, you'll have everything you need during your trip to Lexington!
Oct 22 – 29
$91 per night
Guest favorite
Home in Lexington
Updated historic home! Walk to Rupp/UK/restaurants
If you’re looking for a chic, clean, and comfortable stay in Lexington, look no further. This newly 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.
Aug 9 – 16
$93 per night
Guest favorite
Home in Winchester
Cozy Cottage
Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.
May 12 – 19
$54 per night

Popular amenities for Lexington vacation rentals

Stay near Lexington's top sights

Rupp Arena140 locals recommend
Keeneland164 locals recommend
Hamburg Pavilion46 locals recommend
Fayette Mall38 locals recommend
Kroger Field34 locals recommend
University of Kentucky66 locals recommend

House rentals in Lexington

Guest favorite
Home in Lexington
Distillery District Diamond-pet friendly
Jul 10 – 17
$96 per night
Guest favorite
Home in Lexington
Nomi House, Renovated 1880's shotgun, downtown Lex
Aug 2 – 9
$103 per night
Guest favorite
Home in Lexington
Cozy Country Setting
Oct 12 – 19
$94 per night
Guest favorite
Home in Lexington
Adorable, Clean Lexington Cottage, Convenient to Everything
Feb 20 – 27
$113 per night
Guest favorite
Home in Lexington
Downtown Blue - A new remodeled house in Lexington
Jan 5 – 12
$80 per night
Guest favorite
Home in Lexington
KY & Bourbon & Horses, Oh My! Close to Keeneland
Mar 12 – 19
$92 per night
Guest favorite
Home in Stamping Ground
Buffalo Springs Distilling Company
Jul 17 – 24
$138 per night
Guest favorite
Home in Lexington
My Old Kentucky Home
Jun 8 – 15
$83 per night
Guest favorite
Home in Lexington
Horse Farm Creekside Cabin- 6 min to KY Horse Park
Jul 26 – Aug 2
$199 per night
Guest favorite
Home in Lexington
3BR-4 Beds-2BA close to UK/Chevy Chase/Downtown
Jun 11 – 18
$154 per night
Guest favorite
Home in Harrodsburg
Kentucky Horse Farm Barndo On The Bourbon Trail
Jan 26 – Feb 2
$90 per night
Guest favorite
Home in Lexington
Aldridge- Harris Historic House, Gratz Park
Jul 11 – 18
$84 per night

Other great vacation rentals in Lexington

Guest favorite
Apartment in Lexington
1st Boarding House in Lexington Most Histortic BNB
Jan 3 – 10
$101 per night
Guest favorite
Apartment in Lexington
Game of Thrones - Downtown
Sep 23 – 30
$135 per night
Guest favorite
Cabin in Lawrenceburg
River Side Cabin - Bourbon Trail - HotTub
Nov 7 – 14
$243 per night
Guest favorite
Apartment in Lexington
Private Apartment-Historic Home-Walk Downtown & UK
Feb 1 – 8
$78 per night
Guest favorite
Apartment in Versailles
High style on the Bourbon Trail
Jul 17 – 24
$106 per night
Guest favorite
Condo in Lexington
Top Shelf the only Airbnb in KY above a Distillery
Aug 21 – 28
$332 per night
Guest favorite
Barn in Lexington
Stay with our horses and goats on a private farm
Nov 4 – 11
$81 per night
Guest favorite
Guest suite in Lexington
Close to Keeneland Charming Guest Suite
Jun 5 – 12
$72 per night
Guest favorite
Townhouse in Lexington
Cozy, cute 2BR townhouse near downtown, businesses
Oct 23 – 30
$58 per night
Guest favorite
Guesthouse in Nicholasville
Cottage Retreat - Wine, Horses, Convenient
Jul 14 – 21
$98 per night
Guest favorite
Cabin in Lawrenceburg
Bourbon Trail Cabin on the Farm
Dec 1 – 8
$96 per night
Guest favorite
Guesthouse in Winchester
Carriage House on the Park
Apr 13 – 20
$56 per night

Quick stats about vacation rentals in Lexington

Total rentals

1.6K properties

Rentals with dedicated workspaces

890 properties have a dedicated workspace

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

660 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

89K reviews

Your guide to Lexington

All About Lexington

Located 70 miles east of Louisville in central Kentucky, Lexington has long attracted horse lovers. There are more than 450 horse farms here, surrounded by miles of rolling hills and pastures covered in the lush bluegrass. But there’s more than horses on the brain here.

Kentucky’s second biggest city is also home to a thriving arts scene, including numerous galleries, theatres, music venues. Some of the performance spaces have a long history, such as the Lexington Opera House, which dates back to 1886. Lexington’s universities add to the city’s robust arts calendars at venues like the University of Kentucky Opera Theatre and the Singletary Center for the Arts at the University of Kentucky College of Fine Arts.

You’ll find numerous parks to explore around town and an eclectic range of dining and drinking options, including several wineries and bourbon distilleries. Lexington is also part of the Kentucky Bourbon Trail, which highlights notable distilleries around the state.

The best time to stay in a vacation rental in Lexington

Spring and fall offer pleasant temperatures, making these great times to look for vacation rentals in Lexington. From April through October, the warm weather permits plenty of events to occur, such as a bluegrass festival, one of Kentucky’s oldest music festivals featuring three music stages and a music camp for kids. The Fourth of July celebrations are lively in Lexington as well and include several days of events with musical performances, a parade, food, and a firework display.

As the temperatures drop in late fall and winter, pack a warm coat and boots; however, it’s still a perfect time to tour one of the many distilleries in the area.

Top things to do in Lexington

Raven Run Nature Sanctuary

Located just outside of Lexington, Raven Run is a 734-acre nature sanctuary on the border of the Kentucky River. Miles of hiking and biking trails of varying difficulty levels pass through woodlands, meadows, and streams and provide you with scenic views of the native flora and fauna.

The Arboretum

The State Botanical Garden of Kentucky, also known as the Arboretum, offers 100 acres of green space and tranquility in the middle of busy downtown Lexington. You can wander along two miles of paved pathways and past manicured landscapes that include a Fragrance Garden of roses. Check out the Home Demonstration Garden to gather inspirational ideas for how to best make use of personal green space.

Aviation Museum of Kentucky

Located at the Blue Grass Airport in Lexington, the Aviation Museum of Kentucky covers 20,000 square feet with different aircraft, aviation artifacts and equipment, simulators, and interactive displays. You can watch from the observation area as they work on the airport’s planes or experience a jet taking off from the outdoor viewing area.

Destinations to explore

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