Vacation rentals in Lexington

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Top-rated vacation rentals in Lexington

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Top guest favorite
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.
Home in Lexington
4.95 out of 5 average rating, 382 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.

Top guest favorite
A warm living area is highlighted by natural light from a front window. A cozy seating arrangement is set against a decorative fireplace. A wooden dining table stands nearby, with greenery and décor enhancing the space. A wooden ladder and plants add character to the room.
Home in Lexington
4.98 out of 5 average rating, 122 reviews

The Flower Pot

Welcome to The Flower Pot! Come and stay at our newly renovated mid century modern home complete with a record player collection and great natural sunlight. This location is a hidden gem in Lexington! HIGHLIGHTS: - One turn off main road for easy access to ALL attractions and necessities in Lexington - The Distillery District, Rupp Arena, Keeneland, Red Mile(Railbird Music Festival), UK Campus all approximately 10 MINUTES OR LESS - 1 King bed/ Two Queen Beds with smart TVs - New luxury bathroom

Top guest favorite
A paved driveway stretches into the distance, flanked by lush green grass and a large tree. Wooden fencing borders the property, offering views of rolling hills and a colorful sunset sky above.
Farm stay in Frankfort
4.99 out of 5 average rating, 143 reviews

The Cottage at Seldom Scene Farm - Bourbon Trail

SELF CHECK-IN, CLEAN, PRIVATE OASIS. Restored log home on gorgeous 273 acre farm along the KY RIVER. Serene & natural setting, close to several popular BOURBON TRAIL sites & horse farms. 10 MIN to WOODFORD RESERVE and CASTLE & KEY distilleries. 8 MIN to STAVE Restaurant & Bourbon Bar. Scenic horse farms (ASHFORD, AIRDRIE, WINSTAR). Convenient to KEENELAND, KY HORSE PARK, Versailles, Midway, Frankfort, Lexington, Louisville! Hike, bike, fish, wildlife, sheep, goats, chickens, stars & campfires.

Guest favorite
A stylish bedroom features a spacious bed with light grey bedding and a decorative throw. Natural light fills the room from multiple windows, complemented by a ceiling fan and wooden beams above. A small seating area and a blue dresser add functional elegance.
Apartment in Lexington
4.92 out of 5 average rating, 279 reviews

Sunset Over Lex-Downtown w Deck at Rupp Arena

Spacious, light-filled apartment across from Rupp Arena, walkable to downtown and UK's campus. The bedroom features a king sized Sealy mattress and plush bedding. Enjoy a gorgeous bathroom, full kitchen, and huge second level deck overlooking Rupp. Located in a historic building but newly renovated, top to bottom. Equipped for remote work or relaxation with high speed internet and a Smart TV. Pioneer Split Units for AC and Heat. Free parking for easy access to conventions, concerts, and games.

Top guest favorite
A spacious living area features a comfortable sofa and a cozy chair, complemented by a geometric patterned rug. A coffee table sits in the center, with natural light illuminating the space. The open layout leads to a kitchen visible in the background, enhancing the inviting atmosphere.
Townhouse in North Limestone
4.98 out of 5 average rating, 297 reviews

Explore Bourbon Trail ♥Downtown & Free Parking

#15066671-2 Two spacious bedrooms, each with its very own full on-suite bathroom – think of it as a double dose of hotel-style comfort for the price of one! Not only is our place a cozy haven, but it's also nestled within a vibrant neighborhood...a leisurely stroll away from over a dozen restaurants, bars, craft breweries, a lively farmers market, & the opera house. If you peek out the window, you'll catch a glimpse of the charming Transylvania University campus, which is just a block away.

Top guest favorite
Home in Lexington
4.98 out of 5 average rating, 461 reviews

Distillery District Diamond-pet friendly

This 1948 bungalow in an up-and-coming neighborhood has two bedrooms/one bath. This house has all the updates you could ask of modern living including internet access, TVs with Roku, and keyless entry. Each bedroom has blackout curtains, ceiling fan and bedside power station. The bath is fully stocked with essential personal care items. The fenced-in back yard has a deck and a fire pit. STR Reg #15075605-1. Maximum occupants 4-Guests are prohibited from allowing more than maximum occupancy

Top guest favorite
A red farmhouse tractor is positioned prominently in the foreground, with a vibrant red caboose labeled 'SOUTHERN X525' in the background. An outdoor pavilion with a gabled roof is partially visible, bordered by trees displaying autumn foliage.
Train in Lawrenceburg
4.99 out of 5 average rating, 511 reviews

Bourbon Trail: Caboose on the Farm

Nestled under the shadows of 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 bunkbeds, full bath, kitchenette. Beautiful outdoor pavilion with grill and fire pit. Working cattle farm, see cattle, goats, a donkey, a horse, and a pig!

Top guest favorite
A spacious bedroom features a king bed with a light-colored coverlet against a backdrop of eclectic wall decor and built-in shelving. Textured rugs cover the hardwood floor, while large windows with patterned drapes allow natural light to fill the room, creating a cozy atmosphere.
Apartment in Lexington
4.98 out of 5 average rating, 608 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.

Top guest favorite
A custom California King wooden bed is featured within an immersive room, surrounded by dark hues and dramatic lighting. Adjacent is a unique chair and a traditional rug, enhancing the room's historical charm and fantasy theme.
Apartment in North Limestone
4.98 out of 5 average rating, 534 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

Top guest favorite
The exterior of a two-story brick building is displayed, featuring a welcoming porch with white railings. Lush green trees frame the entrance, and a path leads to the front door. The property exhibits a blend of classic architecture and natural surroundings.
Apartment in Ashland
4.95 out of 5 average rating, 237 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
A modern living area features a comfortable gray sofa with colorful accent pillows, complemented by an elegant coffee table. An artistic mural adorns the wall behind, creating a vibrant focal point. Ambient lighting is provided by stylish floor lamps, enhancing the contemporary decor.
Condo in Bell Court
4.89 out of 5 average rating, 253 reviews

Lexington's Artistic Bunker / 1BR Downtown Condo

Lexington's Artistic Bunker is a space carefully crafted with amenities aplenty! Perfect for the traveling business, medical, or education professional, the guest visiting family/friends, or those experiencing the beauty of the Bluegrass, this modern condo is located in the heart of downtown Lexington. Featuring one bedroom, concrete floors, original murals, walk-in shower, and vaulted ceilings this high-end industrial condo will leave guests satisfied from every angle.

Superhost
A private heated salt-water pool is surrounded by a spacious concrete deck, featuring two black lounge chairs for relaxation. Lush green trees provide a natural backdrop, enhancing the tranquil outdoor space. The pool's clear blue water invites enjoyment and leisure.
Guesthouse in Lexington
4.86 out of 5 average rating, 331 reviews

Cozy studio with private pool and firepit

Welcome to our charming studio apartment located above our detached garage with a private pool. Whether you're looking for a relaxing getaway or a convenient base to explore the city, our cozy studio has everything you need. Close to the following locations: Fayette mall 1.9 miles Bluegrass airport 4.5 miles University of Kentucky 4.6 miles Keeneland 5.1 miles Manchester Music Hall 5.7 miles Rupp Arena 6.4 miles Lexington Opera House 6.5 Please no smoking in the room.

Popular amenities for Lexington vacation rentals

When is the best time to visit Lexington?

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Frequently Asked Questions

  • What are the best places to stay in Lexington?

    Lexington has vibrant neighborhoods like Chevy Chase, downtown, and the Distillery District, where visitors can explore local dining, shops, and parks. Many options feature historic homes, modern lofts, or quiet residential streets with easy access to attractions.

  • What are the best things to do in Lexington with kids?

    Families frequently suggest the Explorium of Lexington, the Kentucky Horse Park, and Jacobson Park for interactive play, nature areas, and horse encounters. Seasonal events and guided farm experiences are also popular with children.

  • What are some of the best things to do in Lexington?

    Explore historic sites, walk through the Distillery District, and discover art galleries around downtown. The Kentucky Horse Park and local bourbon distilleries give glimpses into the region’s equestrian and spirits heritage.

  • How is the weather in Lexington?

    Lexington has cool winters with temperatures from 25–42°F (-4–6°C) and warm, humid summers that reach 87°F (31°C). Spring and fall are comfortable, though rainfall is common throughout the year.

  • What are the best places to visit in Lexington?

    Visitors frequently suggest the Kentucky Horse Park, Ashland – The Henry Clay Estate, and the Distillery District for their cultural, historical, and culinary experiences. The University of Kentucky campus also has impressive architecture and green spaces.

  • What are some hiking trails in Lexington?

    McConnell Springs Park and Raven Run Nature Sanctuary have walking paths and nature trails with opportunities to spot wildlife and native plants. Urban parks such as the Legacy Trail invite walkers and cyclists through city and countryside scenery.

  • What are some family activities we can do in Lexington?

    Explore hands-on exhibits at the Explorium of Lexington, paddle or play at Jacobson Park, and watch interactive farm demonstrations at the Kentucky Horse Park. Outdoor gardens and local ice cream shops are also favorite family stops.

  • What are some of the best day trip ideas from Lexington?

    Plan a guided tour along the Kentucky Bourbon Trail, hike in the Red River Gorge area, or visit historic towns known for local crafts and markets. Scenic drives through horse farm country are also popular.

  • Are there any pet friendly accommodations available in Lexington?

    Many accommodations in downtown, Beaumont, and the Chevy Chase neighborhoods welcome pets. Lexington’s public parks and trails make it accessible to explore with animal companions.

  • What are some local tips for visiting Lexington?

    Embrace the equestrian culture by planning around horse events or morning visits to the track. Exploring local markets, booking bourbon tastings in advance, and trying seasonal produce are often recommended by residents.

  • What is Lexington known for?

    Lexington is recognized for its deep horse industry roots, with historic racetracks and farms. The city also has a thriving bourbon scene, bluegrass music heritage, and an array of local dining traditions.

  • What are the best hidden gems to explore in Lexington?

    Discover quiet trails at Raven Run Nature Sanctuary, local art galleries in the Distillery District, or lesser-known parks like Triangle Park. Small-batch coffee shops and local bookstores add to the city’s under-the-radar appeal.

  • What are the best foods to try in Lexington?

    Lexington’s food scene includes classic Kentucky hot browns, locally made beer cheese, and fried chicken. Flavors from seasonal produce, bourbon-infused treats, and soul food traditions are also frequently suggested.

  • What should I bring for a trip to Lexington?

    Pack comfortable walking shoes for touring farms and neighborhoods, along with layers to adjust for changing weather. Rain jackets and sun protection are useful, especially in spring and summer.

  • What is the nightlife in Lexington like?

    Downtown and the Distillery District feature live music venues, craft cocktail bars, and local breweries, with college sports often energizing the scene. Poetry readings, open mics, and chef-driven late-night menus add variety.

  • What are the most popular events or festivals in Lexington?

    Lexington has Keeneland horse racing meets in spring and fall, which are a well-known tradition. Railbird Festival celebrates music on historic grounds, and bourbon or food festivals around the city often draw a wide range of visitors.

  • Are there family friendly vacation rentals in Lexington?

    Many vacation rentals in neighborhoods like Chevy Chase, Beaumont, and around the University of Kentucky are well suited for families. Features may include extra bedrooms, full kitchens, and access to parks or green spaces.

  • When is the best time to visit Lexington?

    Spring and early fall are often recommended for mild temperatures, vibrant landscapes, and annual events tied to horse racing and bourbon traditions. These seasons also bring outdoor festivals and blooming gardens.

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.

What are the 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.

Quick stats about vacation rentals in Lexington

  • Total vacation rentals

    Explore 1,400 vacation rentals in Lexington

  • Nightly prices starting at

    Lexington vacation rentals start at ﺩ.ﺇ73 per night before taxes and fees

  • Verified guest reviews

    Over 102,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    920 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 590 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    800 properties have a dedicated workspace

  • Wi-Fi availability

    1,370 of Lexington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Lexington rentals

  • 4.8 Average rating

    Lexington stays are highly rated by guests—averaging 4.8 out of 5!

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