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Holiday rentals in Lexington

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Top-rated holiday rentals in Lexington

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Top guest favourite
An aerial view captures a two-story house with a dark roof and a white exterior, positioned next to a well-maintained lawn. A concrete driveway leads to the entrance, with paths of grass lining the edges. Surrounding buildings and greenery are also visible.
Flat in Lexington
4.91 out of 5 average rating, 103 reviews

Victorian Apt Downtown Lexington

Cozy Downtown Retreat - Walk to Rupp Arena & Dining! Welcome to your ideal Lexington getaway! Nestled downtown, our cozy retreat is the city's best at your doorstep. A short walk from Rupp Arena, it's perfect for sports fans, concert-goers, and culture lovers. Enjoy a comfortable stay with a modern living area, fully-equipped kitchen, and plush bed. With top dining, shopping, and nightlife nearby, plus high-speed Wi-Fi and free parking, our home offers everything you need. Book your stay today!

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, 381 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 favourite
A rustic log cabin is partially visible through surrounding greenery. The cabin's wooden exterior is complemented by two windows and a centrally located door, which features a simple design. The natural landscape evokes a serene rural setting.
Cabin in Paris
4.96 out of 5 average rating, 100 reviews

1791 Cabin on Historic Horse Farm

This rare 1791 log cabin is located on Houstondale Farm, a working horse farm in the renowned Bluegrass region of Ky. You can stroll to the barn and visit the horses or enjoy the peace and quiet before relaxing at the pool, complete with a grill and outdoor dining area. It is a scenic 22 minute drive from the Ky Horse Park, 25 minutes from Lexington, and 30 minutes from Keeneland Race Track. Even with the remote feel of the farm you will only be a mile from Walmart, shops & downtown Paris.

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
4.89 out of 5 average rating, 104 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 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.
Flat in Woodward Heights
4.94 out of 5 average rating, 403 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
A cozy living area is highlighted by a fireplace beneath a mounted television. A light green sofa and a beige couch are arranged around a circular coffee table. Natural light filters through the large arched window, complemented by indoor plants placed thoughtfully in the corner.
Home in Lexington
4.94 out of 5 average rating, 129 reviews

Cottage Circle Home

This charming home is nestled in a cozy neighborhood, offering a serene atmosphere and a strong sense of community. Conveniently located, it boasts easy access to a variety of restaurants, catering to different tastes and cuisines, just a short stroll away. Keeneland Racetrack, a track that runs in the fall and spring months, is only 8 minutes from the driveway! Additionally, a nearby grocery store ensures that daily essentials are within reach. Cottage Circle is waiting for YOU! ☺️

Top guest favourite
A serene landscape showcases a gravel path winding through lush green grass, framed by wooden fences. A large tree stands prominently, with the sun rising in the background, casting a warm glow across the misty field under a softly clouded sky.
Home in Versailles
4.95 out of 5 average rating, 227 reviews

Quaint little farm house close to Keeneland/horses

Remodeled beautiful 1900s 2 story house on farm surrounded by Creek and fire pit for your convenience. LOCATION, LOCATION!!! This is the perfect example of having the country in the city! If you are wanting the true feeling of relaxation, this is for you. Amazing views, and close to many famous attractions. 5-10 minutes away... Keeneland The Kentucky Castle Bluegrass Airport Castle Hill Winery Aviation Museum Eckert Orchard also.. Restaurants, Wineries, Breweries, Bourbon Trails

Top guest favourite
An aviation-themed bedroom features a spacious bed with a rich, textured blanket. A desk and chair are positioned beside a brick accent wall, while a stylish black chair adds contemporary flair. Wall art depicting aircraft and a unique light fixture are visible in the softly lit space.
Flat in North Limestone
4.97 out of 5 average rating, 120 reviews

Dramatic Flight - Downtown

This is a 2-bedroom 2-bathroom apartment. One bedroom is an aviation theme decor. The bedrooms are separated by an interior door that can be closed for added privacy. Nestled in the vibrant heart of downtown Lexington, enjoy proximity to trendy cafes, bars, and restaurants. Also includes a full kitchen and laundry. Whether for short or long stays, this sparkling-clean haven offers style and convenience. Immerse yourself in the city's vibrant energy while having a peaceful retreat.

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.
Apartment in Bell Court
4.89 out of 5 average rating, 252 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.

Top guest favourite
A private hot tub is surrounded by lush greenery and hanging ferns. The area features a charming, screened structure with large windows. Soft fabric curtains provide a sense of privacy, while brick pathways lead into a tranquil outdoor setting.
Guest house in Historic South Hill
4.97 out of 5 average rating, 713 reviews

My Old Kentucky Home-Downtown LEX's Premier Stay!

Welcome to My Old Kentucky Home downtowns premier Kentucky themed Air B&B. The best Airbnb in Lexington for a romantic or relaxing getaway! No detail or amenity was spared; private hot tub, plush bath robes, back deck, fire pit, patio and garden with views of the city. Full bourbon bar mixers provided to make your cocktails! ( no alcohol ) Central downtown-1 block from Rupp arena and 3 blocks from UK campus! For a video tour visit the last picture to see the link !

Guest favourite
A comfortable living area features a sectional sofa adorned with colorful cushions and a round coffee table at its center. Framed photographs are displayed on the walls, while light curtains frame the window. A blue accent chair and a potted plant complete the inviting space.
Home in Kenwick
4.93 out of 5 average rating, 216 reviews

The Kenwick - Comfy, Clean, Chic

Lovely downtown Kenwick neighborhood w/ off street parking. Beautifully appointed space w/ amazing queen beds. Updated w/ fast wifi connection. Walking distance to a community coffee house & wine bar, a craft brewery, restaurants, bakeries and a small grocery store. * Rupp Arena 2.5 miles * Keeneland Racetrack 7.5 miles * Kentucky Horse Park 10 miles * STR Reg #15071157-7 - Maximum occupants 4 - Guests are prohibited from allowing more than maximum occupancy *

Top guest favourite
The master bedroom features a spacious bed with a dark blue bedspread, complemented by light-colored pillows. Exposed wooden beams add a rustic touch to the ceiling. A large area rug sits beneath the bed, enhancing the room's warmth. A framed artwork is displayed on the wall.
Home in Georgetown
4.98 out of 5 average rating, 106 reviews

Springside Equine Getaway

Looking for an apartment that is a warm and inviting getaway? In addition to the elegant master bedroom, this apartment can also accommodate 2 additional guest for sleeping on the queen size pullout sofa for a total of 4 guest comfortably. Other additional comforts include a fully stock kitchen with a coffee bar and bathroom amenities. Take time to enjoy the quaint park across the street to experience some downtown Georgetown history to relax and unwind.

Popular amenities for Lexington holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Lexington's top sights

Kentucky Horse Park

527 locals recommend

University of Kentucky

90 locals recommend

Rupp Arena

212 locals recommend

Other great holiday rentals in Lexington

Guest favourite
A modern kitchen features a large island with seating for four, adorned with stylish wooden stools. The sleek cabinetry is complemented by stainless steel appliances and pendant lighting. Natural light floods the space through large windows, providing a bright and airy ambiance.
Home in Woodward Heights
5 out of 5 average rating, 30 reviews

Luxurious 3 BR Distillery District Townhouse

Top guest favourite
Home in Lexington
4.97 out of 5 average rating, 88 reviews

Entire Home Midnight Lexington

Top guest favourite
A spacious living area is showcased with a combination of plush seating, including a brown sofa and two blue armchairs. A large, round coffee table is centered on a decorative area rug, while natural light enters through multiple windows framed by subtle shutters.
Farm stay in Versailles
5 out of 5 average rating, 58 reviews

Dream farmhouse-in heart of horse&bourbon country

Top guest favourite
The front of a newly constructed cabin features a covered porch with two red chairs. A paved pathway leads to the entrance, surrounded by green grass and landscaped areas. The background includes trees and open pastures, contributing to a serene outdoor setting.
Cottage in Georgetown
4.93 out of 5 average rating, 100 reviews

Linden Place LLC

Top guest favourite
A single-story home is set on a well-maintained lawn, featuring a covered front porch with decorative accents. The driveway leads to a spacious garage. A large window allows natural light to enter the entryway, complemented by landscaping around the front, including colorful plants.
Home in Georgetown
5 out of 5 average rating, 57 reviews

Convenient Central Ky Home, 11 mins to Horse Park

Guest favourite
A modern living area features a textured accent wall and warm wooden flooring. A round dining table with four chairs is centrally located, while a cozy seating area with a sofa and colorful cushions is illuminated by natural light from window treatments.
Flat in Lexington
4.91 out of 5 average rating, 91 reviews

Great for extended stays, near Keeneland, dogs ok

Superhost
A charming, dark-colored cottage is set amidst lush greenery. A covered porch is visible at the front, featuring comfortable seating. Flower beds and manicured landscaping enhance the natural surroundings, while tall trees provide shade and tranquility.
Cabin in Versailles
4.88 out of 5 average rating, 90 reviews

Creekside- Bourbon Trail Oasis

Top guest favourite
A wooden staircase with polished steps leads upward, flanked by light-colored walls. At the top of the stairs, a red storage cabinet is positioned, complementing the natural light filtering in from a window. The handrail provides support for ascending.
Flat in Chevy Chase
5 out of 5 average rating, 69 reviews

Cozy, Warm, and Inviting!

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 holiday rentals in Lexington

  • Total holiday rentals

    Explore 1,400 holiday rentals in Lexington

  • Nightly prices starting at

    Lexington holiday rentals start at £15 per night before taxes and fees

  • Verified guest reviews

    Over 102,250 verified reviews to help you choose

  • Family-friendly holiday rentals

    920 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 590 rentals that welcome pets

  • Holiday rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    800 properties have a dedicated workspace

  • Wifi availability

    1,370 of Lexington holiday 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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