Photo by Michael Schuier

Holiday Rentals in Jessamine County

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Top cities in Jessamine County

Check prices for these dates

Our top choices for Jessamine County holiday rentals

1. The Shanklin House by C&K

The Shanklin House by C&K
Nicholasville
10.0 out of 10, Exceptional, (17 reviews)
"We love the Shanklin house, the location, the amenities. "
United States
susan h.
The price is €568
includes taxes & fees
17 Nov - 18 Nov
The Shanklin House by C&K

2. Four+ bedroom historic house near campuses in Wilmore. Fragrance/mold-free

Four+ bedroom historic house near campuses in Wilmore. Fragrance/mold-free
Wilmore
10.0 out of 10, Exceptional, (2 reviews)
"The home was very cozy and the upstairs bathroom had plenty of towels and toiletries! The bedroom itself was very comfortable"
United States
Alena N.
The price is €535
includes taxes & fees
17 Nov - 18 Nov
Four+ bedroom historic house near campuses in Wilmore. Fragrance/mold-free

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

Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail
Lexington
10.0 out of 10, Exceptional, (36 reviews)
"It was the perfect place to spend all of your time away relaxing!"
United States
Meagan B.
The price is €1,049
includes taxes & fees
16 Nov - 17 Nov
Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail

4. Beautiful House in Nicholasville

Beautiful House in Nicholasville
2.0 star property
Nicholasville
The price is €1,234
includes taxes & fees
12 Nov - 13 Nov
Beautiful House in Nicholasville

5. Where urban meets horses and bourbon , is exactly where you will find this adorable Lexington home in 40514. Sky Beauty is a 3 bedroom, 2 bathroom home features a fenced in backyard, updated kitchen, comfortable living room, Apple TV, and so much mor

Where urban meets horses and bourbon , is exactly where you will find this adorable Lexington home in 40514. Sky Beauty is a 3 bedroom, 2 bathroom home features a fenced in backyard, updated kitchen, comfortable living room, Apple TV, and so much mor
Lexington
9.2 out of 10, Wonderful, (104 reviews)
"Perfect house"
United States
Brionna
The price is €227
includes taxes & fees
15 Nov - 16 Nov
Where urban meets horses and bourbon , is exactly where you will find this adorable Lexington home in 40514. Sky Beauty is a 3 bedroom, 2 bathroom home features a fenced in backyard, updated kitchen, comfortable living room, Apple TV, and so much mor

6. Your Home Away From Home

Your Home Away From Home
Lexington
9.8 out of 10, Exceptional, (238 reviews)
"We had a wonderful stay, the house was spacious, comfortable and well equipped. Everything was clean and worked well. Check in and check out were super simple. We enjoyed grilling in the evening in the back yard. We felt like it was a great value and a perfect place to stay for our trip to bourbon country."
United States
John N.
The price is €493
includes taxes & fees
18 Nov - 19 Nov
Your Home Away From Home

7. Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (93 reviews)
"Great place to stay!"
United States
Anna C.
The price is €153
includes taxes & fees
12 Nov - 13 Nov
Treetops Solar Sanctuary

8. 1800’s Historical Log Cabin near I-75 Interstate

1800’s Historical Log Cabin near I-75 Interstate
Lexington
9.4 out of 10, Exceptional, (86 reviews)
"Great location and home for our 10 year anniversary"
United States
Christopher S.
The price is €229
includes taxes & fees
12 Nov - 13 Nov
1800’s Historical Log Cabin near I-75 Interstate

9. Unique Stay in a 1907 Log Cabin on The Kentucky River

Unique Stay in a 1907 Log Cabin on The Kentucky River
Lexington
9.6 out of 10, Exceptional, (114 reviews)
"Cabin was very unique, and charming. Had everything we needed. Steps a little wonky but easy to get through. Would definitely stay again. "
United States
Anonymous traveller
The price is €167
includes taxes & fees
12 Nov - 13 Nov
Unique Stay in a 1907 Log Cabin on The Kentucky River

10. Pool | Hot Tub | Covered Porch | Patio | Game Room

Pool | Hot Tub | Covered Porch | Patio | Game Room
Lexington
9.8 out of 10, Exceptional, (136 reviews)
"Great location. Beautiful house. "
United States
Dan R.
Pool | Hot Tub | Covered Porch | Patio | Game Room

11. Celebrate the best of Kentucky while staying at Kentucky's Best on Berry

Celebrate the best of Kentucky while staying at Kentucky's Best on Berry
Hollywood - Mt. Vernon
10.0 out of 10, Exceptional, (25 reviews)
"Great location and house."
United States
Courtney H.
The price is €421
includes taxes & fees
15 Nov - 16 Nov
Celebrate the best of Kentucky while staying at Kentucky's Best on Berry

12. Welcome to "The Spot" Southland/6 Miles to Keeneland!

Welcome to "The Spot" Southland/6 Miles to Keeneland!
Picadome
9.4 out of 10, Exceptional, (42 reviews)
"Lovely house, well-equipped and perfect for our group. "
United Kingdom
James W.
Welcome to "The Spot" Southland/6 Miles to Keeneland!

13. "The Meridian" Modern Stay near Downtown / Airport with Hot Tub

"The Meridian" Modern Stay near Downtown / Airport with Hot Tub
Lexington
9.8 out of 10, Exceptional, (45 reviews)
"great place"
United States
elizabeth M.
The price is €274
includes taxes & fees
15 Nov - 16 Nov
"The Meridian" Modern Stay near Downtown / Airport with Hot Tub

14. Cozy 1-bedroom in Lexington

Cozy 1-bedroom in Lexington
Lexington
9.8 out of 10, Exceptional, (22 reviews)
"We loved staying at this super lovely little house! It was perfect for two people, everything we needed and great location! If we ever plan a trip to Lexington- this is absolutely where we will stay!"
Canada
Renae
The price is €237
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom in Lexington

15. 💙Modern Downtown with Parking - Keeneland - Horse Park

💙Modern Downtown with Parking - Keeneland - Horse Park
Lexington
9.8 out of 10, Exceptional, (44 reviews)
"Great stay"
United States
chris O.
💙Modern Downtown with Parking - Keeneland - Horse Park

16. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Lexington
9.8 out of 10, Exceptional, (357 reviews)
"Very poor looking motel, both inside and out!"
United States
Miguel
The price is €57
includes taxes & fees
12 Nov - 13 Nov
2 Full Beds | Non-Smoking, Micfridge

17. Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-

Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-
South Broadway Park
9.6 out of 10, Exceptional, (25 reviews)
"We were in town to visit our daughter at UK. Place was cozy, clean, perfect for what we needed. Conveniently located. Keeneland was an easy drive and Kroger field was a really short drive."
United States
Lindsay
Mins to UK- Rupp- Kroger Field- Blocks away to UK & ST Joes Hospital-

18. Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
Lexington
10.0 out of 10, Exceptional, (309 reviews)
"The hosts were very attentive to our needs and made sure we had a happy stay. Would recommend them to anyone and would stay here again."
United States
Alicia C.
The price is €226
includes taxes & fees
12 Nov - 13 Nov
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

19. Quiet Two Bedroom House

Quiet Two Bedroom House
Lexington
9.6 out of 10, Exceptional, (21 reviews)
"Great spot with beautiful views very close to keeneland."
United States
David B.
The price is €250
includes taxes & fees
17 Nov - 18 Nov
Quiet Two Bedroom House

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

Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Downtown Lexington
10.0 out of 10, Exceptional, (62 reviews)
"Very nice unit, walking distance to restaurants and bars"
United States
Paula W.
Lafferty House-Walk to UofK, Woodland Pk, Dn Town, near Bourbon Trl, Horse Farms
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find holiday rentals that suit your style

Find out more about Jessamine County

Everything you need to know about Jessamine County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jessamine County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jessamine County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jessamine County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jessamine County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Jessamine County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jessamine County holiday rentals we have selected for you start as low as €1,234 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jessamine County rentals

At Expedia, we put the best Jessamine County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Jessamine County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jessamine County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jessamine County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.