Photo by Jeff Rogers /Lexington Convention and Visitors Bureau

Lexington holiday lettings

We found 1,010 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Lexington by choosing from 505 houses, 63 flats and other holiday rentals. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include a garden and pool. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Lexington (and vicinity)

Showing deals for:27 Nov - 4 Dec

Pool
Dining
Interior
Property grounds
Exceptional
(63 reviews)

Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport

Versailles

8% off
£4,157
for 7 nights, 1 room
£594 per night
includes taxes & fees
Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport
Living area
Interior
Private kitchen
Private kitchen
Exceptional
(8 reviews)

2-bedroom farmhouse, Lexington. Marimac Farm. 9 minutes to KHP

Lexington

8% off
£1,502
for 7 nights, 1 room
£215 per night
includes taxes & fees
2-bedroom farmhouse, Lexington. Marimac Farm. 9 minutes to KHP
Built in early 1800,s
15 minutes to Woodford Reserve
Original steep & narrow staircase. Guests must OK this before booking accepted.
Entrance/Parlor
Exceptional
(52 reviews)

Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.

Midway

16% off
£852
for 7 nights, 1 home
£122 per night
includes taxes & fees
Railway Guest House in Charming Midway KY Horse Park,Bourbon Trail,Keeneland.
Room
Property grounds
Private kitchen
Dining
Exceptional
(5 reviews)

Sip on bourbon in the hot tub! +hiking & game shed

Frankfort

7% off
£1,839
for 7 nights, 1 cabin
£263 per night
includes taxes & fees
Sip on bourbon in the hot tub! +hiking & game shed
Formal Dining Room
Rear entrance
Den
Rear Entrance Breakfast Room, Kitchen and Den
Exceptional
(71 reviews)

Colliver House at Claybank Farm

Lexington

7% off
£2,018
for 7 nights, 1 home
£288 per night
includes taxes & fees
Colliver House at Claybank Farm
Interior
Living area
Exterior
Living area
Exceptional
(49 reviews)

Loft above Beautiful Horse Barn on Bourbon Trail

Georgetown

8% off
£1,527
for 7 nights, 1 room
£218 per night
includes taxes & fees
Loft above Beautiful Horse Barn on Bourbon Trail
Interior
Steps down to the upper deck
Looking down the driveway to the lake
Great room looking toward the kitchen
Exceptional
(21 reviews)

Herrington Lake Home - Private Dock - Covered Slip

Harrodsburg

8% off
£1,420
for 7 nights, 1 home
£203 per night
includes taxes & fees
Herrington Lake Home - Private Dock - Covered Slip
Interior
Interior
Room
Bathroom
Wonderful
(70 reviews)

Artistic Lodging King Suite

Paris

16% off
£482
for 7 nights, 1 room
£69 per night
includes taxes & fees
Artistic Lodging King Suite
Living area
Terrace/patio
Exterior
Interior
Wonderful
(40 reviews)

Pet-Friendly Bluegrass Retreat w/ Fenced Yard

Georgetown

8% off
£1,184
for 7 nights, 1 home
£169 per night
includes taxes & fees
Pet-Friendly Bluegrass Retreat w/ Fenced Yard
Room
Dining
Private kitchen
Interior
Exceptional
(8 reviews)

Home in Frankfort countryside-close to distilleries, Keeneland &Churchill Downs!

Frankfort

8% off
£2,276
for 7 nights, 1 home
£325 per night
includes taxes & fees
Home in Frankfort countryside-close to distilleries, Keeneland &Churchill Downs!
Interior
Living area
Outdoor dining
Dining
Wonderful
(34 reviews)

Your Kentucky Home

Georgetown

7% off
£1,352
for 7 nights, 1 home
£193 per night
includes taxes & fees
Your Kentucky Home
Master Suite with King Bed
Kitchen
Library - Nook
Our Cottage
Exceptional
(43 reviews)

Charming Kentucky Cottage

Lexington

8% off
£2,942
for 7 nights, 1 home
£420 per night
includes taxes & fees
Charming Kentucky Cottage
Living area
Living area
Private kitchen
Interior
Exceptional
(6 reviews)

The George- Walk Downtown, Popular for Horse Shows, Bourbon Trail, Ark Park

Georgetown

7% off
£1,251
for 7 nights, 1 home
£179 per night
includes taxes & fees
The George- Walk Downtown, Popular for Horse Shows, Bourbon Trail, Ark Park
Deck View
Kitchen Bar
Loft with King Tempur-pedic
Day Lillies in June
Exceptional
(102 reviews)

World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail

Lexington

15% off
£2,462
for 7 nights, 1 home
£352 per night
includes taxes & fees
World Class Horse Farm Minutes To Keeneland, Bluegrass Airport, Bourbon Trail
Room
Dining
Interior
Interior
Exceptional
(28 reviews)

Bourbon Hous - 7 Bdrms, Bar, Billiards, Downtown Lexington

Lexington

7% off
£6,330
for 7 nights, 1 home
£904 per night
includes taxes & fees
Bourbon Hous - 7 Bdrms, Bar, Billiards, Downtown Lexington
Private kitchen
Outdoor dining
Dining
Interior
Exceptional
(9 reviews)

Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location

Lexington

7% off
£1,661
for 7 nights, 1 home
£237 per night
includes taxes & fees
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
Handmade center bar is perfect for preparing a meal.
Breakfast and dinner to the sounds of the creek going by.
On colder days, our two person table is a great way to enjoy a cup of coffee.
Great living room with a wood stove and a rocking chair.
Exceptional
(37 reviews)

Perfect Bourbon Trail Couple Getaway

Frankfort

8% off
£880
for 7 nights, 1 cottage
£126 per night
includes taxes & fees
Perfect Bourbon Trail Couple Getaway
Living area
Private kitchen
Interior
Living area
Exceptional
(12 reviews)

⭐️Renovated⭐️ Great Location Fire Pit - Dog Friendly - Fully Fenced - Games

Lexington

8% off
£2,624
for 7 nights, 1 home
£375 per night
includes taxes & fees
⭐️Renovated⭐️ Great Location Fire Pit - Dog Friendly - Fully Fenced - Games
Electric range. Pots and pans provided.
Gather around large kitchen island with seating for 4
Beautiful dining table with seating for 6 (4 more seats at the island)
View of hall with barn door to basement loaded with games for family fun
Exceptional
(21 reviews)

Great Location / Keeneland / Rupp / Fenced Yard / Games

Lexington

8% off
£2,078
for 7 nights, 1 home
£297 per night
includes taxes & fees
Great Location / Keeneland / Rupp / Fenced Yard / Games
👑The Kingston👑Ready to begin your Bourbon and Horse Adventures?🥃🏇🏼
🍷🍸🍹The Grove ~~ 10 Minutes Away!
♟️Vintage green onyx chess board. Be sure to check out Netflix's Queen's Gambit!
🍽️ Dining for 8 in fully remodeled kitchen! Enjoy the vintage Milo dining table
Exceptional
(24 reviews)

Near KYSHP & Fasig-Tipton Equestrian & Bourbon Tours Central The Kingston!!

Lexington

6% off
£1,959
for 7 nights, 1 home
£280 per night
includes taxes & fees
Near KYSHP & Fasig-Tipton Equestrian & Bourbon Tours Central The Kingston!!
Living area
Dining
Exterior
Private kitchen
Exceptional
(9 reviews)

Equine Escape - 3BR - BBQ Grill - 2-Car Garage

Lexington

8% off
£2,816
for 7 nights, 1 home
£402 per night
includes taxes & fees
Equine Escape - 3BR - BBQ Grill - 2-Car Garage
Interior
Private kitchen
Exterior
Living area
Exceptional
(16 reviews)

Artsy KY-Themed Richmond Gem: Sleeps 8, Centrally Located & 5 mins from Kayaking

Richmond

8% off
£1,394
for 7 nights, 1 home
£199 per night
includes taxes & fees
Artsy KY-Themed Richmond Gem: Sleeps 8, Centrally Located & 5 mins from Kayaking
Terrace/patio
Private kitchen
Room
Interior
Exceptional
(5 reviews)

‘Edith’ Carriage House Getaway - Hamburg/I-75!

Lexington

8% off
£415
for 7 nights, 1 apartment
£59 per night
includes taxes & fees
‘Edith’ Carriage House Getaway - Hamburg/I-75!
Dining
Property grounds
Room
Living area
Exceptional
(41 reviews)

Midnight Lexington Newly Remodeled Designer Stay

Lexington

11% off
£1,434
for 7 nights, 1 home
£205 per night
includes taxes & fees
Midnight Lexington Newly Remodeled Designer Stay

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to theatrical Lexington

Come and experience Lexington and its festivals, theatre scene and art galleries. Renowned for its horse riding, university setting and sporting events, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Lexington

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Lexington a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Kearney Hills Golf Links (5.4 mi / 8.6 km)
  • Keeneland Racing Course (5.9 mi / 9.5 km)
  • The Kentucky Castle (8.4 mi / 13.6 km)
  • Talon Winery (10 mi / 16.1 km)
  • Equus Run Vineyard & Winery (11.1 mi / 17.9 km)
  • The Pavillion (13 mi / 20.9 km)

Exploring the natural landscape of Lexington

Whether you're an adventurous traveller or just want to take in the scenery, Lexington is a great place to get outside. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Masterson Station Park (4.7 mi / 7.5 km)
  • Kentucky River (12 mi / 19.3 km)
  • Raven Run Nature Sanctuary (12.1 mi / 19.5 km)
  • Herrington Lake (24.5 mi / 39.4 km)
  • Lake Reba (25.5 mi / 41 km)
  • Thoroughbred Park (0.6 mi / 1 km)

Travelling to and around Lexington

The nearest airport is in Lexington, KY (LEX-Blue Grass), located 5.5 mi (8.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in Lexington when booking a holiday rental?
When considering a holiday rental in Lexington, Kentucky, a popular area to stay is the historic district. This charming neighbourhood is rich in history and offers a delightful blend of classic architecture and modern amenities. You'll find an array of properties that capture the essence of Lexington, with many situated within walking distance of local attractions.A standout feature of this area is the Mary Todd Lincoln House, the childhood home of the future First Lady, which offers fascinating insights into her life and the Civil War era. Additionally, the nearby Lexington Opera House is a cultural gem, frequently hosting performances and events that showcase local talent and entertainment.Another great option is the area around the University of Kentucky. This vibrant neighbourhood is not only lively, thanks to the student population, but it also boasts beautiful green spaces and access to the university's art museum, which features an impressive collection of American art. Here, you'll find a variety of rental properties that cater to different tastes and budgets.Overall, both the historic district and the university area provide excellent options for holiday rentals, each with its unique charm and proximity to Lexington's top attractions.
How much does it cost to rent a holiday home in Lexington?
Prices for holiday rentals in Lexington vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Lexington to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Lexington holiday house rentals?
You can find great discounts on house rentals in Lexington on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Lexington?
In Lexington, holiday houses are the most popular type of holiday rental, with approximately 1,676 available throughout the area. These properties are often found in residential neighbourhoods and near attractions like the Kentucky Horse Park and the Mary Todd Lincoln House. Most holiday houses feature multiple bedrooms, spacious living areas, fully equipped kitchens, and outdoor spaces such as patios or decks for relaxing after a day of exploring.Apartments are also a popular option, with around 592 available, typically located closer to the city centre and within walking distance of restaurants and shops. These units generally come with modern amenities, including kitchen facilities and comfortable living spaces. Additionally, there are about 232 condos and 140 cottages, which offer unique stays with varying features.
Are there any family house rentals in Lexington?
In Lexington, Kentucky, there are numerous family-friendly house rentals available, with around 345 options scattered throughout the city. Families can find accommodations in neighbourhoods such as Chevy Chase and the historic downtown area, both of which offer ample space and amenities suitable for groups. Many of these properties feature spacious living rooms, fully equipped kitchens, and outdoor areas superb for children to play.Visitors can enjoy close proximity to attractions like the Kentucky Horse Park, where families can explore exhibits and enjoy equestrian events, or the Mary Todd Lincoln House, which offers a glimpse into the history of the area. Additionally, local parks provide great opportunities for outdoor activities, ensuring that families have plenty to do during their stay.
Can I rent a holiday home with a pool or hot tub in Lexington?
In Lexington, there are several holiday homes available for rent that come with pools or hot tubs, with around 34 options to choose from. This charming city, known for its rich equestrian heritage and beautiful landscapes, offers a variety of neighbourhoods where these properties can be found. Areas such as the historic downtown and the scenic countryside surrounding the city are popular choices for travellers seeking relaxation.Many of these rentals feature private pools and hot tubs, providing the ideal setting for unwinding after a day of exploring. Guests can expect amenities such as spacious outdoor areas, fully equipped kitchens for meal preparation, and comfortable living spaces, making them ideal for families or groups.
Can I find long-stay holiday rentals in Lexington?
A long-stay holiday rental in Lexington is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Lexington?
In Lexington, you will find a wide range of pet-friendly house rentals available, with over 260 options to choose from. Many of these properties offer amenities that cater to both humans and pets, such as spacious yards, pet-friendly furnishings, and convenient access to outdoor spaces.The area is known for its beautiful parks, including the scenic Masterson Station Park and the expansive Veterans Park, both of which provide ample opportunities for walking and exercising pets. Additionally, the vibrant downtown area features pet-friendly cafés and shops, ideal for travellers with furry companions.Many holiday homes in Lexington come equipped with modern kitchens, comfortable living spaces, and often outdoor areas where pets can roam freely.
Are there any remote work holiday rentals in Lexington?
In Lexington, Kentucky, there are numerous holiday rentals suitable for remote work, with around 2,272 options available. Many of these properties are equipped with essential amenities to support a productive work environment, including free Wi-Fi, dedicated desks, and comfortable living spaces.The downtown area is particularly appealing for remote workers, offering proximity to local cafes and restaurants where one can enjoy a change of scenery. Additionally, some rentals might feature quiet gardens or outdoor spaces, providing a serene backdrop for working outside.Lexington is known for its vibrant culture and rich history, with attractions such as the Kentucky Horse Park and various local distilleries nearby, making it an excellent choice for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Lexington holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Lexington with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Lexington?
In Lexington, popular holiday rentals typically feature a range of amenities that enhance the stay for visitors. Most properties come equipped with a kitchen, allowing guests to prepare meals at their convenience. Onsite parking is also available, making it easier for travellers with vehicles to explore the area. Additionally, many rentals provide a coffee and tea maker for those who enjoy a warm beverage in the mornings. Guests can also expect outdoor spaces, such as decks or patios, where they can relax and take in the local surroundings.
When is the best time to visit Lexington for a holiday rental?
The peak travel season in Lexington falls between March and May, making it a vibrant time to experience the beauty of the Bluegrass region. During these months, visitors can enjoy the blooming horse farms and the local attractions that come alive with spring festivals and events. With mild temperatures ranging from 10 to 20 degrees Celsius, it's an ideal period for outdoor activities like exploring the scenic trails or visiting the Kentucky Horse Park.July is particularly popular for those seeking a lively option, as it offers ample opportunities for local events and festivals. This month sees many visitors flocking to enjoy the warm weather, superb for outdoor picnics and exploring the city's rich culture.For travellers looking for a more budget-friendly option, consider visiting in December. While this is the low season, it provides a unique charm, with festive decorations adorning the streets and a quieter experience for those who prefer to avoid larger crowds. You'll also find that holiday events and local markets create a wonderful, cheerful atmosphere.Ultimately, the best time to visit Lexington for a holiday rental depends on your preferences.
How early should I book a Lexington holiday rental?
Book your Lexington holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Lexington?
In Lexington, Kentucky, visitors can explore a variety of attractions that highlight the city's rich history and equestrian culture. The Kentucky Horse Park, located just north of the city, is a must-visit for horse enthusiasts, offering engaging exhibits and competitions. Nearby, the historic Mary Todd Lincoln House provides insight into the life of the former First Lady and is set in a charming neighbourhood with beautiful architecture.For those interested in local distilleries, the Distillery District features several bourbon distilleries where you can learn about the production process and enjoy tastings. The area is also home to unique shops and restaurants that reflect the local flair.The Lexington Opera House and the University of Kentucky's campus are both situated in the downtown area, providing cultural experiences and sporting events. The scenic Raven Run Nature Sanctuary offers a tranquil escape with hiking trails that showcase the region's natural beauty.
Can I change or cancel my Lexington home rental booking on Vrbo?
To find Lexington holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Lexington holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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