Vacation rentals in Lexington

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Top-rated vacation rentals in Lexington

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

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Top guest favourite
A modern kitchen features sleek dark cabinetry and stainless steel appliances, offering ample counter space. Natural light floods the room, highlighting the herringbone-patterned floor. A wooden dining table with white, upholstered chairs invites meals together, while decorative shelves accentuate the wall.
Home in Woodward Heights
4.93 out of 5 average rating, 875 reviews

Updated 1910 charm! Walk to Rupp/near Keeneland!

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/sporting event at nearby Rupp Arena (5 min walk), stroll through Gatton Park (2 min walk), view the horse races at Keeneland (10 min drive), tour the Alltech bourbon distillery around the block, or explore the offerings of downtown just outside your front door

Guest favourite
A close-up view captures the bubbling surface of a hot jacuzzi, steam rising gently into the air under a bright sun. The light reflects off the water, creating a serene atmosphere, while trees in the background provide a natural setting.
Home in Lexington
4.91 out of 5 average rating, 225 reviews

Cottage w/Jacuzzi - centrally located, comfy beds!

Keep it simple at this peaceful & centrally-located house with hot, clean jacuzzi year-round (jets are old!). Comfy beds, cozy linens & a good sleep are the hallmark of our BnB. The focus is family, friends & interacting through good ol’ conversation. Plenty of room in kitchen for good meals! Lots of books in the library for a good read & art from local artists - all for sale. Close to downtown, campus, NOLI District, New Circle, I-75/I-64. Great stay for traveling professionals, nurses/doctors.

Top guest favourite
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, 384 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.

Superhost
A spacious sleeping area includes a bed with a light-colored duvet, framed by large windows. A cozy seating area features a plush chair and small table, while an artwork with vibrant colors adds character to the wall. Warm wooden flooring enhances the inviting atmosphere.
Loft in Lexington
4.95 out of 5 average rating, 306 reviews

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!

Top guest favourite
An open living area features large glass doors that provide views of the greenery outside. Industrial elements, such as exposed beams and metal accents, complement a cozy seating arrangement with a sectional sofa and wooden coffee table. A dining table with bar stools is visible in the background.
Condo in Lexington
4.95 out of 5 average rating, 254 reviews

Top Shelf the only Airbnb in KY above a Distillery

The Top Shelf is a space carefully crafted with amenities aplenty! Perched on top of the 90-year-old Pepper Bourbon Distillery, this condo is for the Lexington visitor who likes to be in the middle of the action. Soaring views, three balconies, and all the amenities to make your Bluegrass visit one of a kind. The Top Shelf is perfect for a discerning couple, an adventuring family, or for a group of fun-seekers. Large parties are not allowed. Maximum guests, per LFUCG code restrictions =10

A bright bedroom area features large windows that offer views of Downtown Lexington's skyline. A spacious bed is positioned against a wall, and light-colored curtains frame the windows, allowing natural light to fill the room.
Condo in Lexington
4.81 out of 5 average rating, 134 reviews

175 LEX - Stunning Downtown Views on Main Street!

Offering unparalleled views of Downtown Lexington, immerse yourself into living like a local at 175 LEX! Condo 508 has recently been renovated featuring all the modern-day amenities a guest would desire when visiting Central KY. Residing on the 5th floor, this condo-hotel features one bedroom with a queen-sized bed, living room with sleeper sofa, full kitchen w/ quartz and washer/dryer in-unit. Walkable to Rupp Arena, local restaurants like Carson's, coffee shops, retail shops, & more!

Guest favourite
A spacious living room is highlighted by a large chandelier and a classic fireplace. Elegant furniture includes a gray sofa and two armchairs surrounding a coffee table. Natural light streams through tall windows, and the rich area rug adds warmth to the inviting space.
Townhouse in Lexington
4.88 out of 5 average rating, 249 reviews

The Statesman / Walk to Rupp / Superb Deck

The Statesman, in the heart of Lexington, allows opportunity to experience the conveniences of downtown by foot. This 3-story (stairs only) historic townhouse has undergone a face lift, having spared no expense with high end finishing. Enjoy modern day conveniences while maintaining the old-world charm. **Located above a local bar Henry Clay's Public House; noise is a potential on the second-floor bedroom/living room (3rd floor is less disturbed) from the live music; no parties allowed**

Top guest favourite
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, 611 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 favourite
The exterior of The Dew Drop In is framed by two large trees, showcasing a well-manicured lawn. The house, painted in light colors, is set back from the foreground, with a wraparound porch visible. A wooden fence outlines the property, enhancing the natural setting.
Farm stay in Midway
5 out of 5 average rating, 119 reviews

Saxony Farm - The Dew Drop In

Nestled in the heart of Kentucky's Bluegrass region, The Dew Drop In, (newly constructed in 2018) is located on Saxony Farm, a working Thoroughbred horse farm, family-owned and operated for over 50 years. More than just a place to rest your head, guests will experience a home-away-from-home location, & enjoy the peace and quiet of farm life, all within striking distance of downtown Lexington, KY's Bourbon Trail, locally-owned restaurants, shops and numerous family-friendly activities.

Top guest favourite
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, 538 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

Guest favourite
Two outdoor bathtubs are positioned on a wooden deck, surrounded by trees and views of the creek. An Adirondack chair sits nearby, providing a space for relaxation while enjoying the natural surroundings.
Treehouse in Georgetown
4.92 out of 5 average rating, 282 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

Top guest favourite
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

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.

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 $28 CAD 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 and 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

  • Wifi availability

    1,370 of Lexington vacation rentals include wifi 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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