A historic stone building with two towers and a sign for The Old Taylor Distillery Company.

Photo by Steve Coy

Woodford County holiday rentals

We found 610 holiday rentals — enter your dates for availability

Discover a selection of 34 homes and other holiday rentals in Woodford County that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Woodford County destinations on Stayz

Versailles

A train station with a cafe, a building labeled 'TESTING TRAINING,' and a black car parked on the platform.

Midway

Holiday rentals with weekly discounts – Woodford County

Showing deals for:20 Nov - 27 Nov

Exceptional

(63 reviews)

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

Versailles

8% off

AU$7,747

for 7 nights, 1 room

AU$1,107 per night

includes taxes & fees

Exceptional

(102 reviews)

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

Lexington

16% off

AU$4,452

for 7 nights, 1 home

AU$636 per night

includes taxes & fees

Exceptional

(8 reviews)

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

Lexington

8% off

AU$2,814

for 7 nights, 1 room

AU$402 per night

includes taxes & fees

Retreat and unwind after a long day in the 6 person hot tub

Living room with 65" Smart TV and plenty of seating

Exceptional

(21 reviews)

Bourbon Trail Cabin-Sleeps 10-Hot Tub, Firepit by Iconiq Stays

Lawrenceburg

8% off

AU$5,571

for 7 nights, 1 home

AU$796 per night

includes taxes & fees

Exceptional

(28 reviews)

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

Lexington

8% off

AU$12,240

for 7 nights, 1 home

AU$1,749 per night

includes taxes & fees

Exceptional

(8 reviews)

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

Frankfort

8% off

AU$4,265

for 7 nights, 1 home

AU$609 per night

includes taxes & fees

Original steep & narrow staircase. Guests must OK this before booking accepted.

Exceptional

(52 reviews)

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

Midway

16% off

AU$1,605

for 7 nights, 1 home

AU$229 per night

includes taxes & fees

Exceptional

(12 reviews)

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

Lexington

8% off

AU$4,319

for 7 nights, 1 home

AU$617 per night

includes taxes & fees

Exceptional

(36 reviews)

Cozy, Fun, Relaxing 4Bd, 2Bth Home near Keeneland.

Lexington

8% off

AU$3,368

for 7 nights, 1 home

AU$481 per night

includes taxes & fees

Wonderful

(34 reviews)

Your Kentucky Home

Georgetown

8% off

AU$2,641

for 7 nights, 1 home

AU$377 per night

includes taxes & fees

Exceptional

(6 reviews)

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

Georgetown

7% off

AU$2,357

for 7 nights, 1 home

AU$337 per night

includes taxes & fees

Exceptional

(9 reviews)

Brick Hous - Downtown Lexington

Lexington

8% off

AU$10,452

for 7 nights, 1 home

AU$1,493 per night

includes taxes & fees

King Bedroom, Seating Area & Workstation

Exceptional

(26 reviews)

Luxurious 3 BR Distillery District Townhouse - Eight Belles

Lexington

8% off

AU$4,791

for 7 nights, 1 home

AU$684 per night

includes taxes & fees

Exceptional

(7 reviews)

"The Dawning House" - Peaceful Modern Stay w/ Yard

Georgetown

8% off

AU$2,895

for 7 nights, 1 home

AU$414 per night

includes taxes & fees

Open dining area perfect for meals or gathering together

Exceptional

(9 reviews)

Georgetown Getaway, Sleeps 6, Fenced Yard (Pet-Friendly), Near Lexington & I-75

Georgetown

8% off

AU$5,061

for 7 nights, 1 home

AU$723 per night

includes taxes & fees

View of hall with barn door to basement loaded with games for family fun

Gather around large kitchen island with seating for 4

Beautiful dining table with seating for 6 (4 more seats at the island)

The family room from the entry area with 60" Samsung smart TV (byo logins)

Exceptional

(21 reviews)

Great Location / Keeneland / Rupp / Fenced Yard / Games

Lexington

8% off

AU$3,130

for 7 nights, 1 home

AU$447 per night

includes taxes & fees

Exceptional

(6 reviews)

Horse & Bourbon - 2.5 miles from Buffalo Trace

Frankfort

11% off

AU$4,470

for 7 nights, 1 home

AU$639 per night

includes taxes & fees

Exceptional

(13 reviews)

Castle Glow - 2BR - BBQ Gr - Walk to Kroger Field

Lexington

7% off

AU$2,788

for 7 nights, 1 home

AU$398 per night

includes taxes & fees

Excellent

(8 reviews)

"The Homestead" UPSCALE STAY - Downtown with Yard

Lawrenceburg

8% off

AU$2,736

for 7 nights, 1 home

AU$391 per night

includes taxes & fees

Exceptional

(14 reviews)

Botherum Carriage House, Garden Lovers Delight

Lexington

8% off

AU$13,498

for 7 nights, 1 home

AU$1,928 per night

includes taxes & fees

Exceptional

(12 reviews)

Game Room | King Suite | Firepit | Patio | Grill

Georgetown

8% off

AU$3,715

for 7 nights, 1 home

AU$531 per night

includes taxes & fees

Unwind in our 7-person hot tub against a mural of KY views and bourbon bottles.

Craft your favorite dishes in our modern and fully equipped kitchen.

Fave spot for morning coffee and nightcaps.

Elevate your vacation dining meals in this space.

Exceptional

(41 reviews)

Hot Tub, Beautifully Renovated Historic Home in the Heart of the Bourbon Trail

Frankfort

10% off

AU$4,857

for 7 nights, 1 home

AU$694 per night

includes taxes & fees

Exceptional

(38 reviews)

Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington

Lexington

8% off

AU$1,266

for 7 nights, 1 apartment

AU$181 per night

includes taxes & fees

Like wine? This winery is almost at your doorstep at less than a 10 min drive.

Fun awaits you at Double Shot on Main. It is bigger than it looks.

Deck with seating for 4, a table and gas grill.

Queen master bedroom w/ en suite bathroom, Roku TV, closet & electric fireplace.

Exceptional

(141 reviews)

2 Bed/2 Bath/Game Room

Lawrenceburg

8% off

AU$1,969

for 7 nights, 1 home

AU$281 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find the best place to stay - Woodford County

Thoroughbred Estate 10 minutes from Keeneland, Midway, Versailles 8000sqft +pool

Sleeps 12 · 4 bedrooms · 4+ bathrooms

Premier Host

River Retreat: Private Cabin Getaway on the Bourbon Trail

Sleeps 6 · 2 bedrooms · 1 bathroom

Premier Host

Sugar Hill Farm-Historic Horsefarm with Pool

Sleeps 9 · 4 bedrooms · 2+ bathrooms

Premier Host

Cozy cabin in the heart of horse country

Sleeps 8 · 3 bedrooms · 2 bathrooms

Luxe Bourbon Trl~Game Rm~Golf Sim~Hot Tub~Fire Pit

Sleeps 10 · 5 bedrooms · 4+ bathrooms

Premier Host

Riverside Roost -bourbon themed waterfront home

Sleeps 6 · 3 bedrooms · 2 bathrooms

Choose a holiday rental for your Woodford County getaway

Learn about the unique charm of Woodford County with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Woodford County

Are you hoping to find attractions to see in the city? Venture out of your holiday home and experience everything that makes Woodford County a one-of-a-kind holiday spot. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

The Kentucky Castle (4.2 mi / 6.8 km)
Keeneland Racing Course (6.7 mi / 10.8 km)
Lovers Leap Vineyards and Winery (8.4 mi / 13.5 km)
Equus Run Vineyard & Winery (8.7 mi / 14 km)
Kearney Hills Golf Links (11.6 mi / 18.7 km)
Cherry Blossom Golf and Country Club (16.8 mi / 27 km)

Exploring the natural landscape of Woodford County

Whether you're looking for adventure or just want to appreciate the scenery, Woodford County is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

Masterson Station Park (10.2 mi / 16.3 km)
Raven Run Nature Sanctuary (21.5 mi / 34.5 km)
Herrington Lake (22.6 mi / 36.3 km)
Anderson County Community Park Lake (9.5 mi / 15.4 km)
Capitol View Park (11.8 mi / 19 km)
The Arboretum State Botanical Garden of Kentucky (12.5 mi / 20.1 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Woodford County?

Based on our data, houses are the most popular type of property in Woodford County. But as you'd expect, everyone's idea of the perfect stay isn't going to be the same. Stayz has holiday homes of all sizes, shapes and budgets, and we'll help you find the perfect fit for you.

How much does it cost to rent a holiday home in Woodford County?

Property type, length of stay and season are some things that can influence the price of a holiday home. Simply add your dates of travel to find your ideal fit. From cosy cabins to sprawling villas, all Stayz holiday homes offer unbeatable value.

How much does it cost to rent a beach house in Woodford County?

When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday home. Put in your Woodford County travel dates to view your available options on Stayz. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want in your beach house.

What are popular home amenities in Woodford County?

Some of the most popular home amenities people prefer in Woodford County include a stovetop, an oven and a fridge. Whether you're on a trip with family, your besties or even pets, Stayz holiday homes provide the best amenities for fun and relaxation with the people you cherish the most.

Are there large group holiday homes in Woodford County?

You'll find nine holiday properties in Woodford County that can accommodate a group of five or more guests. From family getaways to special occasions like birthday parties, these stays have enough room to gather with the people that matter the most.

Can I find two-bedroom holiday homes in Woodford County?

Woodford County has six two-bedroom properties for you to select from. Experience a holiday home with all the space and privacy you want at an attractive price on Stayz.

Are there holiday homes with WiFi in Woodford County?

Whether you'd like to keep up with the latest news, send a few emails or update your social media accounts, there are 10 holiday homes with WiFi in Woodford County. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.

How old do you have to be to rent a holiday home in Woodford County?

The minimum age is normally 16, 18 or 21. It can change between properties on Stayz, so look at the rules of your preferred Woodford County holiday home before booking.

How long can I rent a holiday home in Woodford County for?

It's up to the Woodford County property. To see all available options offering extended stays, just type your dates and number of people into Stayz's search page. You can enjoy having the entire property to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and a yard where your little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

More holiday ideas

Holiday homes