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Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Jessamine County cottages

Fridge, microwave, oven, stovetop
Modern cottage located in the heart of the Bourbon Trail

Cottage in Lawrenceburg

9.8 out of 10, Exceptional, (33)
"Had a great stay here! Beautiful and unique property, comfortable, very convenient location for seeing Lawrenceburg and visiting Wild Turkey/Four Roses/Buffulo Trace, etc. I would definitely stay there again."
United States
Roger C.
Modern cottage located in the heart of the Bourbon Trail
Property grounds
Beautifully updated riverside 1840 cottage on the bourbon trail near Danville

Cottage in Perryville

10.0 out of 10, Exceptional, (30)
"Loved our stay, very clean and a great location. Enjoy the shops next door. We enjoyed the back patio and the games provided."
United States
Pamela W.
Beautifully updated riverside 1840 cottage on the bourbon trail near Danville
Interior
Cozy Cottage Perfect for Girls Night Away

Cottage in Lexington

10.0 out of 10, Exceptional, (14)
"This place is just charming. We were in town for our daughter’s graduation from UK and your place was perfect. Spacious and so comfy. "
United States
jodi i.
$598 nightly
The price is $694
Dec 10 - Dec 11
Total with taxes and fees
Cozy Cottage Perfect for Girls Night Away
Exterior
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.

Cottage in Frankfort

10.0 out of 10, Exceptional, (36)
"Loved this quaint farmhouse cottage"
United States
Sandy F.
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
House (3 Bedrooms) | Interior
11 Mi to Danville: Family Home in Lancaster

Cottage in Lancaster

3.0 star property
11 Mi to Danville: Family Home in Lancaster
House (4 Bedrooms) | Interior
Spacious Frankfort Retreat on Bourbon Trail!

Cottage in Frankfort

3.0 star property
Spacious Frankfort Retreat on Bourbon Trail!
3 bedrooms, iron/ironing board, WiFi, bed sheets
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark

Cottage in Georgetown

10.0 out of 10, Exceptional, (4)
"Great stay! Will be back again. "
United States
Traci B.
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Exterior
Capital City Cottage

Cottage in Frankfort

8.6 out of 10, Excellent, (43)
"Inside was very clean, and well maintained. Location is within mins of everything. Very easy to get around from here. Thank you. "
United States
Danny S.
$205 nightly
The price is $241
Jan 7 - Jan 8, 2026
Total with taxes and fees
Capital City Cottage
Exterior
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Cottage in Lexington

10.0 out of 10, Exceptional, (17)
"Simply a great experience start to finish"
United States
Joyce E S.
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
House (3 Bedrooms) | Front of property
10 Mi to Keeneland: Family Home w/ Deck & Yard

Cottage in Lexington

3.0 star property
10.0 out of 10, Exceptional, (1)
"I liked the porch and the pergola. My granddaughter ran around the house in bare feet and her feet got incredibly dirty. Floors probably need a good cleaning. That was the only begative i had."
United States
Tanya
10 Mi to Keeneland: Family Home w/ Deck & Yard
Property grounds
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.

Cottage in Frankfort

10.0 out of 10, Exceptional, (21)
"Wonderful property and owners."
United States
Karen M.
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Exterior
Ideal One-Bedroom Getaway on the Bourbon Trail

Cottage in 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
$175 nightly
The price is $193
Dec 11 - Dec 12
Total with taxes and fees
Ideal One-Bedroom Getaway on the Bourbon Trail
Outdoor spa tub
Twin Cottages **** Presale**** cottage #7

Cottage in Lawrenceburg

$355 nightly
The price is $397
Dec 10 - Dec 11
Total with taxes and fees
Twin Cottages **** Presale**** cottage #7
Exterior
Springside BoHo Getaway

Cottage in Georgetown

9.8 out of 10, Exceptional, (54)
"Great place! We will stay here again. "
United States
Zeppelin F.
$282 nightly
The price is $311
Dec 10 - Dec 11
Total with taxes and fees
Springside BoHo Getaway
Property grounds
Five Minutes from Keeneland!

Cottage in 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.
$293 nightly
The price is $323
Dec 11 - Dec 12
Total with taxes and fees
Five Minutes from Keeneland!
House (3 Bedrooms) | Interior
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

Cottage in Kenwick

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Outdoor dining
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable

Cottage in Georgetown

10.0 out of 10, Exceptional, (2)
"Thank you for a wonderful stay your house is beautiful and loved all the small details right down to coming in to a vase of fresh flowers. We came down for my husband’s 40th birthday Celebration and Thanksgiving, with our four kids. The board games were a huge hit, we played for hours. They had so many to choose from. The back yard was so incredibly relaxing and the jacuzzi was wonderful. Thank you for making this experience unforgettable, this house does not lack a single thing, the kitchen has...
United States
Jessica G.
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
House (3 Bedrooms) | Interior
Our Lakeside Retreat w/ Deck on Lake Herrington!

Cottage in Lancaster

3.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed everything about the property "
United States
Jessica
Our Lakeside Retreat w/ Deck on Lake Herrington!
Microwave, oven, stovetop
Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants

Cottage in Georgetown

9.4 out of 10, Exceptional, (3)
"Husband said the location was perfect for travel to work very clean communication with owner was excellent"
United States
Joni Z.
Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants
Exterior
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail

Cottage in Lawrenceburg

10.0 out of 10, Exceptional, (14)
"Very clean place to stay. "
United States
Alisha F.
$334 nightly
The price is $357
Dec 10 - Dec 11
Total with taxes and fees
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
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

Staybridge Suites Lexington S Medical Ctr Area by IHG

Staybridge Suites Lexington S Medical Ctr Area by IHG

10/10 Excellent
"Great location, friendly staff"
TARA 1-night trip
Posted 21 hours ago
Staybridge Suites Lexington S Medical Ctr Area by IHG

Find out more about Jessamine County

Jessamine County Cottages information

Number of reviews
301
Accommodation
47 Cottages
Lowest Price
$193
Highest Price
$694

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