448 Lexington Vacation Rentals & Short Term Rentals

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Compare Lexington vacation rentals from 6 rental sites including HomeAway, Booking.com, HRS Holidays and more, ranging from $25 to $1670 a night.

Information about Lexington

About Lexington

Lexington, Kentucky is a “first class” city in more ways than one. It is just one of two cities—the other being Louisville—designated as a “first class” city based on its population and form of government. But Lexington is also “first class” in terms of the local people, attractions, and cuisine. The city is in the center of the inner Bluegrass Region, and is noteworthy for its fertile soil, excellent pastureland and horse and stock farms. It’s called “the horse capitol of the world” for a number of reasons, including the fact that Lexington was the first city outside of Europe to host the World Equestrian Games, and that there are over 500 horse farms in the area. Lexington is also a very smart city, coming in 10th among US cities in terms of college education rate. It turns out that around 40% of the population has at least a bachelor’s degree. It’s a smart place to visit for those who enjoy culture and natural beauty—and a love of horses.

Things to Do in Lexington

Lexington is known as the best place in the world for raising thoroughbred horses, and there’s a story of how all that came to be. The 1,200 acre Kentucky Horse Park is a good place to start learning more about Lexington’s horse industry, from its museums, galleries, demonstrations, and 40+ breeds of horses. The American Saddle Horse Museum will clue you in on the native Kentucky breed, and the Keeneland Race Course is open for tours all year round, even when there’s no meet taking place. You can also try a Horse Farm Tour to visit Kentucky’s four-legged celebrities in their natural element. If horses don’t float your boat but you still enjoy the great outdoors, the Raven Run Nature Sanctuary has hiking trails through historic landmarks, and guided tours at night for stargazing. The largest mall in Kentucky is in Lexington, but Downtown Lexington also has a wide selection of shops, sights, and restaurants. If you’re planning a summer trip into Lexington, the Mayfest Arts Fair takes place in Lexington over Mother's Day weekend every year. In June, there’s the Festival of Bluegrass, Kentucky’s oldest bluegrass music festival, followed by the Broadway music festival. Lexington’s Fourth of July festival is also a big deal, lasting for several days before the grand finale. Festivities in Lexington continue throughout August and September with the Woodland Arts Fair and Festival Latino de Lexington, the biggest fiesta in September.

Lexington Day Trips

The largest restored Shaker Village in the world is in Pleasant Hill, which is less than 30 miles from Lexington. It was named a top hidden travel destination by BBC News, although with 34 buildings on 3,000 acres of land, “hidden” is debatable. Visitors can spend a day exploring the preserve and experiencing the life of a Shaker, or stay awhile in one of the unique accommodations in Shaker Village. Frankfort, the capitol of Kentucky, may not be as well known as Louisville or Lexington, but has an interesting history despite being the fifth-smallest state capitol in the United States. Frankfort is around a 40-minute drive from Lexington, but has a free trolley in the city that provides access to local historic sites. Louisville, possibly one of the better-known cities of Kentucky, is about an hour and a half drive from Lexington. There are buses to and from Louisville for as low as $14, and the city has much to offer in terms of attractions and things to do. Louisville is the legendary home of the Kentucky Derby, the world’s largest underground zip line and the Muhammad Ali Center.

Lexington Accommodation

If you want to be right in the center of things, then Downtown Lexington is your best bet. Downtown hotels are close to the Bluegrass Airport, the Convention Center, Keeneland Race Course and the Kentucky Horse Park. This area has abundant dining options and nightlife. The Keeneland Race Course area is popular for those in town specifically for the races. However, its still close enough to Downtown Lexington and Blue Grass Airport in terms of convenience and getting around. If you want a change of pace or atmosphere, the University of Kentucky campus is right on the edge of downtown. This area will have a lot more student and school-affiliated traffic. If you want to get away from the city vibe entirely, accommodations near the horse parks may provide just the seclusion you need. There’s a lot more breathing room out towards the farms, with stretches of pastureland all around.

Lexington Transportation

The LexTran, or Lexington Transit Authority, is the main form of public transportation in the city. There are 42 buses that navigate 10 routes, with the main line that runs from 5:30 AM to 8:20 PM. The bus fare is $1 including unlimited transfers on one-way trips, and children under the age of 6 ride free of charge. If you want to catch a ride out of Lexington, the Greyhound Bus station is on the north side of town. Another option is the Hoosier Ride service, provided by Miller Transportation, which also has routes throughout Kentucky, Indiana, Ohio, and even Tennessee.

Vacation Rentals in Lexington

Find the best Lexington vacation rentals with Tripping.com. Choose from 449 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $1670 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 285 of homes in Lexington offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 152 rentals with pool or jacuzzi, or relax with the family in one of the 203 homes with cable TV.

For all those dog lovers and cat lovers, Lexington offers 111 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 6 rental sites in Lexington where the top providers in that area are HomeAway, Booking.com, and HRS Holidays. There are 138 HomeAway rentals, 135 Booking.com short term rentals and 94 HRS Holidays vacation rentals.