Jessamine County Holiday Rentals

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Our top choices for Jessamine County holiday rentals

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
Lexington
10.0 out of 10, Exceptional, (25 reviews)
"Very clean and easy to access. Several fun amenities. Messages were quickly answered and easy to communicate. We would definitely stay here again."
United States
Robert S.
Spacious Retreat with Heated Pool-Hot Tub-Games-Bar-Near Keeneland&Bourbon Trail
Exterior

The Lodge A-Frame Getaway

The Lodge A-Frame Getaway
Nicholasville
The price is HK$2,407
HK$4,504 total
includes taxes & fees
19 Feb - 20 Feb
The Lodge A-Frame Getaway
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
Nicholasville
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful home!"
United States
Leah G.
The price is HK$2,306
HK$4,702 total
includes taxes & fees
19 Feb - 20 Feb
This 19th century farmhouse has been given new life with a thoughtful restoration by Castle & Key
Interior

Bourbon Trail: Caboose on the Farm

Bourbon Trail: Caboose on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (38 reviews)
"Loved every aspect of this unique stay! From the very cool caboose to friendly farm animals, we hope to be back again!"
United States
Cindi M.
The price is HK$1,108
HK$1,854 total
includes taxes & fees
1 Mar - 2 Mar
Bourbon Trail: Caboose on the Farm
Property grounds

Bourbon Trail Cabin on the Farm

Bourbon Trail Cabin on the Farm
Lawrenceburg
10.0 out of 10, Exceptional, (49 reviews)
"Awesome place. Just stayed overnight but will be back just to relax in the cabin. The surroundings are so peaceful and the animals were fun. "
United States
Rachel P.
The price is HK$739
HK$1,392 total
includes taxes & fees
22 Feb - 23 Feb
Bourbon Trail Cabin on the Farm
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
Lexington
9.6 out of 10, Exceptional, (108 reviews)
"Stayed for one night to ease a long drive to Florida. Would recommend and dog friendly."
United States
Ashley G.
The price is HK$742
HK$1,406 total
includes taxes & fees
1 Mar - 2 Mar
Unique Stay in a 1907 Log Cabin on The Kentucky River
Interior

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay

East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Georgetown
10.0 out of 10, Exceptional, (60 reviews)
"Great place to stay -- perfect location, wonderful host, beautiful accomodations, and sweet welcome dog on top of it all! Highly recommended. "
United States
l v.
The price is HK$977
HK$1,766 total
includes taxes & fees
15 Mar - 16 Mar
East Suite-🕊️ Bleubird Studio + Suites -Art Gallery • Yoga • Boutique Stay
Smart TV, fireplace, books

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, (59 reviews)
"Friendly host, warm welcoming home. Loved all the antiques and it was very comfortable!"
United States
J K.
The price is HK$938
HK$1,860 total
includes taxes & fees
8 Mar - 9 Mar
1800’s Historical Log Cabin near I-75 Interstate
Property grounds

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.

This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Georgetown
8.6 out of 10, Excellent, (33 reviews)
"We had a beautiful stay. This house has a wonderful home feel! It was clean and had everything we needed. We will be back! "
United States
Corrie S.
The price is HK$625
HK$1,384 total
includes taxes & fees
12 Mar - 13 Mar
This house is a 2 bedroom(s), 1 bathrooms, located in Georgetown, KY.
Exterior

Bourbon Trail Lakehouse - Pet Friendly!

Bourbon Trail Lakehouse - Pet Friendly!
Frankfort
9.8 out of 10, Exceptional, (52 reviews)
"Great place to stay!"
United States
Jeff S.
The price is HK$657
HK$1,969 total
includes taxes & fees
19 Feb - 20 Feb
Bourbon Trail Lakehouse - Pet Friendly!
Smart TV, stereo

Comfy Upstairs 2 bed/1 bath near EKU in Richmond

Comfy Upstairs 2 bed/1 bath near EKU in Richmond
Richmond
10.0 out of 10, Exceptional, (41 reviews)
"I had a great stay!"
United States
Cody C.
The price is HK$598
HK$1,047 total
includes taxes & fees
19 Feb - 20 Feb
Comfy Upstairs 2 bed/1 bath near EKU in Richmond
TV, offices

Nestled amongst the site of Old Graham Springs is where you will find The Blue Cottage

Nestled amongst the site of Old Graham Springs is where you will find The Blue Cottage
Harrodsburg
9.6 out of 10, Exceptional, (27 reviews)
"Very nice and cute place. Everything was easy, like being at home. I only had one question for them and it was answered within minutes. Easy walk to downtown. "
United States
Barb P.
The price is HK$742
HK$1,532 total
includes taxes & fees
4 Mar - 5 Mar
Nestled amongst the site of Old Graham Springs is where you will find The Blue Cottage
Smart TV

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, (33 reviews)
"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 HK$598
HK$1,047 total
includes taxes & fees
19 Feb - 20 Feb
Cozy upstairs 2 bed/1 bath Richmond apt near EKU
Outdoor dining

Original Circa 1818 Oak Lodge

Original Circa 1818 Oak Lodge
Lawrenceburg
9.4 out of 10, Exceptional, (53 reviews)
"Great communication. Very clean property."
United States
Alan D.
The price is HK$1,172
HK$2,163 total
includes taxes & fees
2 Mar - 3 Mar
Original Circa 1818 Oak Lodge
Interior

Five Minutes from Keeneland!

Five Minutes from Keeneland!
Versailles
10.0 out of 10, Exceptional, (23 reviews)
"In Bluegrass Country yet close to Keeneland and all the other important places and activities around Lexington and surrounds. "
United States
Thomas M.
The price is HK$1,414
HK$2,524 total
includes taxes & fees
21 Feb - 22 Feb
Five Minutes from Keeneland!
Interior

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.

Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Frankfort
8.8 out of 10, Excellent, (97 reviews)
"We enjoyed our stay while we were down for Breyer Fest. It was close to places we wanted to go and quiet. We would definitely stay here again."
United States
Jacob Y.
The price is HK$547
HK$1,287 total
includes taxes & fees
21 Feb - 22 Feb
Capital City Condo #6 close to Interstate, Water Park, Restaurants and Shopping.
Exterior

Downtown Danville Luxury House, walk to restaurants & bars, dog friendly

Downtown Danville Luxury House, walk to restaurants & bars, dog friendly
Danville
9.6 out of 10, Exceptional, (28 reviews)
"Everything was great."
United States
Melissa Y.
Downtown Danville Luxury House, walk to restaurants & bars, dog friendly
Exterior

2 Bed/2 Bath/Game Room

2 Bed/2 Bath/Game Room
Lawrenceburg
10.0 out of 10, Exceptional, (123 reviews)
"Great central location for our stay! Than you so much. Would absolutely recommend this to everyone!"
United States
Patrick
The price is HK$1,016
HK$1,671 total
includes taxes & fees
24 Feb - 25 Feb
2 Bed/2 Bath/Game Room
TV, offices

It's rare to find a place that's both historic & one-of-a-kind

It's rare to find a place that's both historic & one-of-a-kind
Harrodsburg
9.8 out of 10, Exceptional, (56 reviews)
"The property was lovely, welcoming, and cozy. It was a perfect place for a getaway weekend."
United States
Erica H.
The price is HK$625
HK$1,227 total
includes taxes & fees
4 Mar - 5 Mar
It's rare to find a place that's both historic & one-of-a-kind
Smart TV, books

Capital City Condo #2

Capital City Condo #2
Frankfort
9.2 out of 10, Wonderful, (60 reviews)
"Location was close to all the places we were visiting. Love the white towels too. "
United States
Mary L.
The price is HK$547
HK$1,287 total
includes taxes & fees
19 Feb - 20 Feb
Capital City Condo #2
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"The room was great, and the place was very convenient. "
Thomas 1-night trip
Posted 2 days ago
Hyatt Regency Lexington