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Holiday houses in Lexington

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Quick stats about holiday rentals in Lexington

  • Total holiday rentals

    Explore 1,360 holiday rentals in Lexington

  • Nightly prices starting at

    Lexington holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 105,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    910 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 640 rentals that welcome pets

  • Holiday rentals with a pool

    100 properties feature pools

  • Rentals with dedicated workspaces

    800 properties have a dedicated workspace

  • Wi-Fi availability

    1,350 of Lexington holiday 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!

Top-rated holiday 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 Lexington
4.93 out of 5 average rating, 924 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

Top Guest favourite
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
4.99 out of 5 average rating, 187 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 favourite
A charming exterior view of a single-story home is framed by a white picket fence, with a small seating area accessible by the entrance. Trees with autumn foliage create a colorful backdrop, and a clear blue sky enhances the welcoming appearance of the residence.
Home in Georgetown
4.92 out of 5 average rating, 132 reviews

The Clayton House | Chic & Cozy

Welcome to our stylish, newly renovated 2-bedroom, 1-bath home, centrally located just minutes away from Georgetown College! This spacious gem boasts an inviting open full-kitchen and living room concept, a back patio, and back yard. Whether you're visiting the college, exploring the town, or simply looking for a comfortable and modern retreat, The Clayton House is the ideal choice for your stay. Experience the perfect blend of convenience and comfort in this newly revitalized space. *No pets

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
4.94 out of 5 average rating, 266 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

Top Guest favourite
Home in Stamping Ground
4.97 out of 5 average rating, 736 reviews

Buffalo Springs Distilling Company

It’s recently been brought to our attention about Airbnb scams! Please reserve with us or someone else that has a history! The Bourbon Trail The Buffalo Springs Distilling Company got it's start in 1868. It closed and it's warehouses were emptied out by the 1970's. This building is one of the last structures left on the site. This historic building was the main office and gatehouse for visitors to the distillery, so we can offer one Queen sized bedroom due to the size of the structure.

Superhost
An interior space is shown with a spacious bed in the foreground. A glass garage door opens to a private patio area. Wood paneling adorns the walls, complemented by a television and storage shelves. Natural light fills the room, enhancing a sense of openness.
Apartment in Lexington
4.91 out of 5 average rating, 450 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!

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
5.0 out of 5 average rating, 132 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 Lexington
4.98 out of 5 average rating, 554 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 favourite
A spacious living area features a comfortable sofa adorned with patterned pillows. Natural light illuminates the wooden ceiling and warm tones of the furnishings. A decorative area rug complements a coffee table, while soft lighting from side tables enhances the inviting atmosphere.
Townhouse in Lexington
4.97 out of 5 average rating, 117 reviews

Modern Townhome Close to UK

Welcome to this modern townhome, located in the desirable Chinoe neighborhood. Steps away from Chinoe Shopping Center, you'll find a supermarket, salon, and several restaurants. It's just a quick drive to Kroger Field, and a short drive to the heart of downtown. So whether you're here to place a bet at the Keeneland racetrack, attend a concert at Rupp Arena, tour one of our many bourbon distilleries, or cheer on the Wildcats, you'll find that this townhome is in a convenient location.

Top Guest favourite
A classic bungalow features a welcoming front porch, framed by two trees and a well-maintained lawn. The home is set back from the sidewalk, showcasing a path leading to the entrance. A spacious fenced yard is visible to the side, providing a private outdoor space.
Bungalow in Lexington
4.97 out of 5 average rating, 264 reviews

Cozy Kenwick Bungalow in the Heart of Lexington

Welcome to your home away from home in Kenwick, one of Lexington's favorite neighborhoods! This classic bungalow has 3 bedrooms (queen beds in 2 rooms and 2 twin beds in another room) plus a bright basement room with a sleeper sofa. Sit outside on the covered front porch or sit on the back deck and enjoy the fenced in yard. Kenwick is centrally located and is an easy drive to many popular destinations including downtown, UK, the bourbon trail, the Kentucky Horse Park, and Keeneland.

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 Lexington
4.88 out of 5 average rating, 277 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.

Guest favourite
A polished copper bar counter reflects a variety of bourbon bottles and mixers. A cocktail shaker and glass sit ready for use, accompanied by a stylish ice bucket. The arrangement provides a glimpse into a well-equipped space for cocktail preparation.
Guesthouse in Lexington
4.94 out of 5 average rating, 594 reviews

The Bourbon House- Downtown Lex’s Premier Air B&B

Welcome to "The Bourbon House" Downtown Lexington's Premier spot to stay for an authentic Kentucky experience. This cottage was built by me from the ground up with no details spared to immerse my guests in the finest things Kentucky has to offer- Fully stocked bourbon bar mixers! (You supply bourbon) Hand crafted house and furnishing from reclaimed wood and bourbon barrels, private hot tub, bathrobes, garden, fire pit, and walking distance to downtown and Rupp arena

Popular amenities for Lexington holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Lexington's top sights

Kentucky Horse Park

535 locals recommend

University of Kentucky

93 locals recommend

Rupp Arena

213 locals recommend

The Arboretum, State Botanical Garden of Kentucky

162 locals recommend

Raven Run Nature Sanctuary

147 locals recommend

Mary Todd Lincoln House Historical Marker

97 locals recommend

Other great holiday rentals in Lexington

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
4.89 out of 5 average rating, 264 reviews

The Statesman / Walk to Rupp / Superb Deck

Guest favourite
Condo in Lexington
4.9 out of 5 average rating, 185 reviews

💙The FLAT @ the LEX w/ Parking-Horse Park-Bourbon

Top Guest favourite
The open concept living area features a comfortable green sofa, a round coffee table, and a cozy ottoman. A television is positioned on a stylish media console, while shelves display various books and decor. Natural light enters through a large window, enhancing the inviting environment.
Guesthouse in Lexington
4.96 out of 5 average rating, 324 reviews

Fully sanitized, private Carriage House + King Bed

Top Guest favourite
A serene outdoor area is highlighted by a covered patio featuring comfortable seating and a hot tub. Ambient lighting creates a cozy atmosphere, while lush green grass and carefully placed shrubs enhance the inviting outdoor space.
Home in Georgetown
4.96 out of 5 average rating, 200 reviews

The Luxe/Hot Tub/12min to Horse Park/30 Min to Ark

Guest favourite
The kitchen features wooden cabinetry and black appliances, including a stove and microwave. A double sink is positioned near a window that allows natural light. Counter space is available for food preparation, with dish towels and a kitchen mat visible on the floor.
Condo in Lexington
4.83 out of 5 average rating, 408 reviews

*Gorgeous Hideout | Close to Everything*

Top Guest favourite
Cabin in Nicholasville
4.98 out of 5 average rating, 49 reviews

The Lodge at Marble Creek

Superhost
Place to stay in Lexington
5.0 out of 5 average rating, 3 reviews

2 King 2 Bath Luxury Acoustic Suite Downtown

Guest favourite
Home in Lexington
4.99 out of 5 average rating, 73 reviews

Ralph Lauren Inspired, Walk to Rupp Arena, Parking

When is the best time to visit Lexington?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$211 NZD$221 NZD$231 NZD$288 NZD$266 NZD$288 NZD$233 NZD$231 NZD$239 NZD$278 NZD$244 NZD$227 NZD
Avg. temp1°C3°C8°C13°C19°C23°C25°C24°C21°C14°C8°C3°C

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.

Destinations to explore