Photo by Michael Schuier

Jessamine County holiday rentals

We found 572 holiday rentals — enter your dates for availability
Discover a selection of 22 homes and other holiday rentals in Jessamine County that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as a fireplace and garden. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Popular Jessamine County destinations on Stayz

Holiday rentals with weekly discounts – Jessamine County

Showing deals for:6 Nov - 13 Nov

Room
Dining
Interior
Pool
Exceptional
(62 reviews)

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

Versailles

8% off
AU$7,843
for 7 nights, 1 room
AU$1,120 per night
includes taxes & fees
Raven Fox Farm-Country Charm! 5 BR Only 8 miles from Keeneland and BG Airport
Living area
Hot tub has 33 jets
Upstairs loft is a perfect retreat for guests on the 2nd floor
3 seats at the kitchen island and 4 seats at the table in adjoining dining area
Exceptional
(21 reviews)

Our Cottage is a perfect retreat for adults only in beautiful bluegrass region

Lexington

7% off
AU$2,969
for 7 nights, 1 cottage
AU$424 per night
includes taxes & fees
Our Cottage is a perfect retreat for adults only in beautiful bluegrass region
Opening March 20!  The heated, saltwater pool is ready for your family to enjoy!
Enjoy the hot tub any time and you'll have a special view!
A fully loaded, true chef's kitchen awaits your culinary creations!
Our kitchen is spacious enough for everyone to help cook!
Exceptional
(32 reviews)

Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail

Nicholasville

11% off
AU$9,986
for 7 nights, 1 home
AU$1,427 per night
includes taxes & fees
Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail
Dining
Outdoor dining
Private kitchen
Living area
Exceptional
(9 reviews)

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

Lexington

7% off
AU$2,401
for 7 nights, 1 home
AU$343 per night
includes taxes & fees
Boho-Glam Bungalow 2 Kings, Fire Pit, Fenced Yard, Pet Friendly, Prime location
Interior
Private kitchen
Dining
Living area
Exceptional
(12 reviews)

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

Lexington

8% off
AU$4,242
for 7 nights, 1 home
AU$606 per night
includes taxes & fees
⭐️Renovated⭐️ Great Location Fire Pit - Dog Friendly - Fully Fenced - Games
Master Suite with King Bed
Kitchen
Our Cottage
Family Room
Exceptional
(43 reviews)

Charming Kentucky Cottage

Lexington

8% off
AU$5,628
for 7 nights, 1 home
AU$804 per night
includes taxes & fees
Charming Kentucky Cottage
Terrace/patio
Living area
Room
Living area
Exceptional
(31 reviews)

Minutes to Keeneland/Airport/UK & more!

Lexington

8% off
AU$3,175
for 7 nights, 1 home
AU$454 per night
includes taxes & fees
Minutes to Keeneland/Airport/UK & more!
Room
Dining
Exterior
Living area
Exceptional
(9 reviews)

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

Lexington

8% off
AU$4,290
for 7 nights, 1 home
AU$613 per night
includes taxes & fees
Equine Escape - 3BR - BBQ Grill - 2-Car Garage
Private kitchen
Private kitchen
Springtime in Kentucky!
Living area
Exceptional
(54 reviews)

Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants

Lexington

8% off
AU$6,034
for 7 nights, 1 home
AU$862 per night
includes taxes & fees
Elegant Equestrian-Themed Home Minutes From Keeneland, Airport & Restaurants
Exterior detail
Interior
Room
Private kitchen
Exceptional
(74 reviews)

Luxurious 1-bedroom with Free Parking

Lexington

7% off
AU$1,350
for 7 nights, 1 home
AU$193 per night
includes taxes & fees
Luxurious 1-bedroom with Free Parking
Living area
Terrace/patio
Private kitchen
Interior
Exceptional
(12 reviews)

“Ivory Inn” Modern Stay w/ Hot Tub - Greyline

Lexington

8% off
AU$3,893
for 7 nights, 1 home
AU$556 per night
includes taxes & fees
“Ivory Inn” Modern Stay w/ Hot Tub - Greyline
Beautiful dining table with seating for 6 (4 more seats at the island)
Gather around large kitchen island with seating for 4
Electric range. Pots and pans provided.
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

7% off
AU$3,106
for 7 nights, 1 home
AU$444 per night
includes taxes & fees
Great Location / Keeneland / Rupp / Fenced Yard / Games
Front living room
King bedroom
Kitchen with subway tile
Front entrance
Exceptional
(11 reviews)

Stylish Mid-Century Modern Home 5 minutes to downtown

Lexington

14% off
AU$2,140
for 7 nights, 1 home
AU$306 per night
includes taxes & fees
Stylish Mid-Century Modern Home 5 minutes to downtown
Living area
Property grounds
Exterior
Room
Exceptional
(41 reviews)

Midnight Lexington Newly Remodeled Designer Stay

Lexington

11% off
AU$2,709
for 7 nights, 1 home
AU$387 per night
includes taxes & fees
Midnight Lexington Newly Remodeled Designer Stay
Interior
Kitchen
Interior
King Bedroom, Seating Area & Workstation
Exceptional
(26 reviews)

Luxurious 3 BR Distillery District Townhouse - Eight Belles

Lexington

8% off
AU$4,851
for 7 nights, 1 home
AU$693 per night
includes taxes & fees
Luxurious 3 BR Distillery District Townhouse - Eight Belles
Living area
Interior
Interior
Interior
Exceptional
(11 reviews)

"The Berry" Mid-Century Modern Stay w/ 3BR - UK

Lexington

8% off
AU$3,923
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
"The Berry" Mid-Century Modern Stay w/ 3BR - UK
Cook a feast or just brew your morning coffee. This fully equipped kitchen with granite counters and french doors makes every meal a pleasure.
Relax in our private backyard hot tub under ambient solar-powered string lights! Open year-round! (just please no glass in the hot tub).
Your new favorite reading spot. Sink into the hanging egg chair and lose yourself in a good book.
Pull up to your home away from home
Exceptional
(54 reviews)

Relaxing Hot Tub | S’mores Fire Pit | Garage

Lexington

8% off
AU$3,159
for 7 nights, 1 home
AU$451 per night
includes taxes & fees
Relaxing Hot Tub | S’mores Fire Pit | Garage
Interior
Outdoor dining
Exterior
Interior
Exceptional
(36 reviews)

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

Lexington

8% off
AU$1,281
for 7 nights, 1 apartment
AU$183 per night
includes taxes & fees
Cozy 1-bedroom apt in Victorian Era House minutes walking to Downtown Lexington
Terrace/patio
Beautiful anytime of day or night
Living area
View from second floor bedroom
Exceptional
(14 reviews)

Botherum Carriage House, Garden Lovers Delight

Lexington

8% off
AU$13,667
for 7 nights, 1 home
AU$1,952 per night
includes taxes & fees
Botherum Carriage House, Garden Lovers Delight
Property grounds
Private kitchen
Interior
Private kitchen
Exceptional
(21 reviews)

Horse and Bourbon Lover’s Farm Cabin - 2 bed/2 bath in Versailles, KY

Versailles

8% off
AU$2,083
for 7 nights, 1 cabin
AU$298 per night
includes taxes & fees
Horse and Bourbon Lover’s Farm Cabin - 2 bed/2 bath in Versailles, KY
Private kitchen
Exterior
Living Room
Room
Exceptional
(55 reviews)

Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

Lexington

26% off
AU$2,726
for 7 nights, 1 apartment
AU$389 per night
includes taxes & fees
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms

Find the perfect holiday rental for your Jessamine County getaway

Learn about the unique charm of Jessamine County with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Jessamine County

Are you looking for top things to see and do in the city? Venture out of your holiday home and check out everything that makes Jessamine County a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Talon Winery (7.3 mi / 11.7 km)
  • Keeneland Racing Course (11.7 mi / 18.8 km)
  • The Kentucky Castle (12.3 mi / 19.7 km)
  • Bright Leaf Golf Course (17.3 mi / 27.8 km)
  • Equus Run Vineyard & Winery (19.6 mi / 31.6 km)
  • Paradise Cove Aquatic Center (19.7 mi / 31.7 km)

Exploring the natural features in Jessamine County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Jessamine County is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Raven Run Nature Sanctuary (10 mi / 16.1 km)
  • Herrington Lake (12.3 mi / 19.8 km)
  • Masterson Station Park (15.2 mi / 24.4 km)
  • Lake Reba (20.2 mi / 32.6 km)
  • The Arboretum State Botanical Garden of Kentucky (10 mi / 16.1 km)
  • Kentucky River (10.7 mi / 17.2 km)

Frequently asked questions

What is the best area to stay in Jessamine County when booking a holiday home?
Wilmore is among the most popular areas for a Stayz holiday home in Jessamine County. Consider our range of comfortable stays and then get ready to experience the best of this destination.
What is the most popular type of holiday home accommodation in Jessamine County?
According to our data, houses are the most desirable holiday home type in Jessamine County. But that goes without saying, everyone's idea of an epic trip isn't the same. Stayz has holiday homes in a variety of shapes and sizes, and we'll help you find the perfect fit for you.
How much does it cost to rent a holiday home in Jessamine County?
The average price for a holiday home in Jessamine County is determined by a number of factors, such as property type, season and length of stay. Whether you're searching for a villa with space for extended family or a quaint cabin for just you and the kids, just enter your dates of travel to view stays with great value.
How much does it cost to rent a beach house in Jessamine County?
The average price for a holiday home near the beach in Jessamine County depends on when you'll be there and the type and size of property you want. Find prices easily on Stayz by entering your preferred travel dates. Then make use of the filter tool to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.
What are popular home amenities in Jessamine County?
When it comes to home amenities that guests search for in Jessamine County, an oven, a stovetop and a fridge rank highest. With Stayz holiday homes, you'll find options to match your style and taste, whether you're taking a trip with family members, friends or even pets.
Are there large group holiday homes in Jessamine County?
With four properties that can sleep 10 or more people in Jessamine County, you won't have to keep anyone off the invite list. From fun family holidays to special events like birthday parties and weddings, Stayz will help you find a large group home to match the occasion.
Can I find two-bedroom holiday homes in Jessamine County?
Gather your family and experience complete comfort and privacy in one of the two two-bedroom holiday properties Jessamine County has to offer.
Are there holiday homes with WiFi in Jessamine County?
Jessamine County has eight holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Stayz homes make it a cinch to get online.
How old do you have to be to rent a holiday home in Jessamine County?
We recommend checking with the Jessamine County holiday property you're considering on Stayz as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Jessamine County for?
It's down to the Jessamine County property. To look at a list of options offering extended stays, simply enter your dates and guest number into the Stayz search page. Look forward to having the entire property to yourself, as well as amenities such as air conditioning, a kitchen and outdoor spaces where the kids can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.

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