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Holiday Rentals in Jessamine County

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Our top choices for Jessamine County holiday rentals

TV
This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key

This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key

This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key
Nicholasville
10.0 out of 10, Exceptional, (12)
"Beautiful home!"
United States
Leah G.
This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key
Terrace/patio
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

Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail
Lexington
10.0 out of 10, Exceptional, (25)
"We had a wonderful family vacation with our children, grandchildren and even great grandma. The house was clean and comfortable and perfect for all ages. The location was close to many things and we enjoyed the country setting to sit around the fire pit at night. We definitely recommend this stay. "
United States
Amy M.
The price is €800
includes taxes & fees
15 Dec - 16 Dec
Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail
Smart TV, fireplace, books
Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38)
"Staying in the Caboose on the Farm was such a fun and relaxing escape. The space was clean, cozy and full of charm with beautiful views and friendly animals. It was the perfect mix of comfort and nature. Highly recommend for anyone looking for a unique getaway!"
United States
Lindsey
Bourbon Trail: Caboose on the Farm
Smart TV
Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Cozy upstairs 2 bed/1 bath Richmond apt near EKU

Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Richmond
10.0 out of 10, Exceptional, (32)
"Always a great stay. We’ve stayed here several times, and will continue to do so when we visit our daughter at EKU. "
United States
Angela B.
The price is €119
includes taxes & fees
13 Dec - 14 Dec
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Smart TV, books
Capital City Condo #2

Capital City Condo #2

Capital City Condo #2
Frankfort
9.2 out of 10, Wonderful, (59)
"My husband and I stayed for 4 nights and this condo was a great place to come back to each evening to relax. Easy check in/check out, location was a bit run down but never had any problems or felt unsafe so don't let that discourage you from choosing this place for your stay in Frankfort. "
United States
Carrie D.
The price is €145
includes taxes & fees
12 Dec - 13 Dec
Capital City Condo #2
Exterior detail
Treetops Solar Sanctuary

Treetops Solar Sanctuary

Treetops Solar Sanctuary
Chevy Chase
10.0 out of 10, Exceptional, (84)
"Great location in beautiful neighborhood! "
United States
Tiffany S.
The price is €132
includes taxes & fees
14 Dec - 15 Dec
Treetops Solar Sanctuary
Property grounds
Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (12)
"We stayed for our anniversary and visited some of the distilleries in the area. Our cabin was so cool and our stay was great. We would definitely book again"
United States
Evan C.
The price is €318
includes taxes & fees
4 Jan - 5 Jan 2026
Bourbon Barrel Cottages #2 on Ky. Bourbon Trail
Interior
Five Minutes from Keeneland!

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23)
"This wonderful property is in the heart of lovely horse farms. Minutes from the airport, Keeneland Race Track and downtown Lexington. Super easy to find and so warm and welcoming. Just perfect for adventures. "
United States
Heidi D.
The price is €282
includes taxes & fees
13 Dec - 14 Dec
Five Minutes from Keeneland!
2 bedrooms, free WiFi, bed sheets
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.

This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
2.0 star property
Downtown Lexington
9.4 out of 10, Exceptional, (13)
"Great location and huge place. Gorg windows and high ceilings. I stayed here for a friends wedding and loved it. Will stay again next time I’m in town! "
United States
Londyn
This apartment is a 2 bedroom(s), 1 bathrooms, located in Lexington, KY.
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Springside BoHo Getaway

Springside BoHo Getaway

Springside BoHo Getaway
Georgetown
9.8 out of 10, Exceptional, (54)
"Great place! We will stay here again. "
United States
Zeppelin F.
The price is €272
includes taxes & fees
14 Dec - 15 Dec
Springside BoHo Getaway
Smart TV, fireplace, books
Unique Stay in a 1907 Log Cabin on The Kentucky River

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, (107)
"Stayed for one night to ease a long drive to Florida. Would recommend and dog friendly."
United States
Ashley G.
Unique Stay in a 1907 Log Cabin on The Kentucky River
Smart TV, books
Capital City Condo #8

Capital City Condo #8

Capital City Condo #8
Frankfort
8.6 out of 10, Excellent, (36)
"The condo was good for an overnight stay. The owners were very responsive & kind. Very close to just about anything you want to do. The price was good for the accommodations. Thank you for the hospitality! "
United States
Pollee F.
Capital City Condo #8
Exterior
Ideal One-Bedroom Getaway on the Bourbon Trail

Ideal One-Bedroom Getaway on the Bourbon Trail

Ideal One-Bedroom Getaway on the Bourbon Trail
LAWRENCBURG
10.0 out of 10, Exceptional, (13)
"This little house was perfect. Very clean and well-kept. Modernly decorated. Walking distance to the little downtown area, the park and the town square. We loved our short stay! "
United States
Kristi
Ideal One-Bedroom Getaway on the Bourbon Trail
Fridge, microwave, oven, stovetop
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.

3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.

3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Frankfort
10.0 out of 10, Exceptional, (31)
"Great spot to rest and recuperate after a long day on the Bourbon trail!"
United States
Jonathan F.
The price is €269
includes taxes & fees
10 Jan - 11 Jan 2026
3 Bedroom 2 Bath home located on farm land/private but only 2 minutes from town.
Exterior
This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.

This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.

This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.
2.0 star property
Frankfort
9.6 out of 10, Exceptional, (14)
"Very nice kept and clean will be booking again "
United States
Donald
This house is a 0 bedroom(s), 2 bathrooms, located in Frankfort, KY.
Fridge, microwave, oven, stovetop
Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Richmond
9.8 out of 10, Exceptional, (84)
"Clean, close to campus . Would definitely stay again. "
United States
Christina K.
The price is €184
includes taxes & fees
12 Dec - 13 Dec
Modern 2bd 2ba - Near I75, No Steps, Free Wifi
Living area
The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!

The Bourbon Garage- walking distance to Buffalo Trace!
Frankfort
10.0 out of 10, Exceptional, (8)
"Super convenient to buffalo trace. Comfortable space. Would recommend "
United States
Brandy
The price is €215
includes taxes & fees
12 Dec - 13 Dec
The Bourbon Garage- walking distance to Buffalo Trace!
Smart TV, fireplace
Luxury on Main / South

Luxury on Main / South

Luxury on Main / South
Richmond
10.0 out of 10, Exceptional, (44)
"Great place for a quick weekend getaway."
United States
Jennifer
The price is €175
includes taxes & fees
21 Dec - 22 Dec
Luxury on Main / South
Microwave, oven, stovetop
Miss Reba's Love is a charming house with a warm Kentucky feel.

Miss Reba's Love is a charming house with a warm Kentucky feel.

Miss Reba's Love is a charming house with a warm Kentucky feel.
2.0 star property
Frankfort
10.0 out of 10, Exceptional, (7)
"Very clean and communication with host was excellent. Would recommend to anyone. "
United States
Chuck F.
The price is €307
includes taxes & fees
12 Dec - 13 Dec
Miss Reba's Love is a charming house with a warm Kentucky feel.
Interior
Bourbon on Broadway

Bourbon on Broadway

Bourbon on Broadway
2.0 star property
Frankfort
10.0 out of 10, Exceptional, (21)
" wanted to visit. Just a nice place to stay big enough for taking Really enjoyed it. "
United States
Anonymous traveller
The price is €210
includes taxes & fees
14 Dec - 15 Dec
Bourbon on Broadway
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.
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Top Jessamine County Hotel Reviews

Everhome Suites Lexington - Horse Park

Everhome Suites Lexington - Horse Park

10/10 Excellent
"The kitchen was stocked. The bathroom was clean. The heat was adequate. The lobby was very clean and smelled so good.The bed pillows were very small though."
Garry 1-night trip
Posted 1 day ago
Everhome Suites Lexington - Horse Park

Find out more about Jessamine County

Holiday Homes in Jessamine County

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