Vacation rentals in Lexington
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Top-rated vacation rentals in Lexington
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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
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 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
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!
Charming Cottage Home on a Horse Farm in the City!
Charming cottage on a 20-acre horse farm just minutes from Downtown Lexington, Midway, Keeneland, the Horse Park, and LEX Airport. Enjoy country calm with city convenience and quick access to I-64/I-75 for Bourbon Trail trips and visits to Louisville or Cincinnati. The cottage offers a one bedroom with a king size bed and two twin beds total of 4 guest maximum, full kitchen, living area, WiFi, cable TV, and total privacy. Dogs welcome with prior approval- PET FEE is 35.00 PER DAY/ PER DOG
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.
KY’s #1 Wishlisted Stay-Treehouse and outdoor tubs
Escape to Kentucky’s 2026 most wishlisted Airbnb! A romantic treetop getaway with two outdoor tubs, twinkle lights, and a peaceful setting made for reconnecting. The treehouse features a large glass rolling garage door allowing stunning views of the sunset. 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 ✔ Hot Water
Hidden Gem|One Bedroom Apt Downtown Lexington
Our One Bedroom Apartment is conveniently located near Downtown Lexington; University of Kentucky, Transylvania, Thoroughbred Park, The Legacy Trail, Restaurants, Fine Dining & Nightlife. It is a Guest Favorite for many travel nurses! They call it their favorite tucked away spot. Martine’s Pastry conveniently located next door. Walk-able to nearby yoga studios, Historic Lyric Theater, Cup of Commonwealth Coffee Shop & Carson's Steakhouse. Approximately, 5 miles from I-75\I-64.
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
Lovely Downtown Apt 1 Block from Rupp!
Walk to Rupp and all downtown has to offer from this cozy, one bedroom apartment. The space is outfitted with a Smart TV, plush linens and towels, brand new washer/dryer, all new appliances, basic kitchen amenities and free off street parking on the premises for an effortless stay in downtown Lexington. If this is your first time booking with us, welcome! We look forward to hosting you again soon. if you have stayed with us before, thanks for your loyalty.
Hidden View Cabin
Welcome to Hidden View Cabin, a delightful cabin where seeing wildlife and listening to the sounds of nature are yours to enjoy! Take the scenic drive down the gravel lane to this private and peaceful place located among pine trees and overlooking a one acre pond. Whether you have come to relax and get away from it all or want to visit the many attractions throughout central Kentucky this is the place for you. Only 20 minutes from Lawrenceburg.
*Bourbon, Bourbon, Bourbon*
Just named to the Best Places to Stay in Bourbon Country, this modern Bourbon-themed townhouse is in Lexington's Northside, close to the Jefferson St retail corridor, West 6th Brewing & Rupp Arena. It's an ideal pad for exploring Bourbon Country, a Keeneland weekend, or cheering on the UK Wildcats. You will be within a 5 minute walking radius of a distillery, brewery, and the Legacy trail.
Popular amenities for Lexington vacation rentals
Stay near Lexington's top sights
House rentals in Lexington
4br/3ba/5bed Home, Walk to Chevy Chase/UK/downtown
Lexington's Commonwealth Cottage STR:15070620-1
Buffalo Springs Distilling Company
Cozy Cottage
Horse Farm Creekside Cabin- 6 min to KY Horse Park
Cozy 1-bedroom in Lexington
The Clayton House | Chic & Cozy
Newly renovated upscale house with high ceilings
Other great vacation rentals in Lexington
Horse and Bourbon Lover’s Cabin
Modern Townhome Close to UK
Nonie's Abode
Paradise Inn B&B - Honeymoon Suite
*Charming Two Bed, Two Bath Apt with Balcony*
Creekside- Bourbon Trail Oasis
Modern Farm Loft
Hillside Farm & Creek - A Bourbon Trail Retreat
When is the best time to visit Lexington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$26,153 GYD | G$27,408 GYD | G$28,663 GYD | G$33,057 GYD | G$32,430 GYD | G$30,547 GYD | G$28,873 GYD | G$28,663 GYD | G$29,710 GYD | G$34,522 GYD | G$30,337 GYD | G$28,245 GYD |
| Avg. temp | 1°C | 3°C | 8°C | 13°C | 19°C | 23°C | 25°C | 24°C | 21°C | 14°C | 8°C | 3°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.
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 1,420 vacation rentals in Lexington
Nightly prices starting at
Lexington vacation rentals start at G$4,184 GYD per night before taxes and fees
Verified guest reviews
Over 102,340 verified reviews to help you choose
Family-friendly vacation rentals
900 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 620 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
1,390 of Lexington vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Gym, and BBQ grill across Lexington rentals
4.9 Average rating
Lexington stays are highly rated by guests—averaging 4.9 out of 5!
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- Ark Encounter
- Kentucky Horse Park
- Buffalo Trace Distillery
- Rupp Arena
- University of Kentucky
- Castle & Key Distillery
- Four Roses Distillery Llc
- The Arboretum, State Botanical Garden of Kentucky
- Raven Run Nature Sanctuary
- Shaker Village of Pleasant Hill
- McConnell Springs Park
- Lovers Leap Vineyards and Winer
- Old Fort Harrod State Park
- Talon Winery & Vineyards
- Cove Spring Park
- Equus Run Vineyards
- Kroger Field
- Fort Boonesborough State Park
- Masterson Station Park