Photo by Michael Schuier

Cottages in Jessamine County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Jessamine County cottages

Property grounds
Beautifully updated riverside 1840 cottage on the bourbon trail near Danville

Cottage in Perryville

Beautifully updated riverside 1840 cottage on the bourbon trail near Danville
10.0 out of 10, Exceptional, (31)
"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

Cozy Cottage Perfect for Girls Night Away
10.0 out of 10, Exceptional, (14)
"This house is just as cute as the pictures with enough space for a large group. It’s also located within walking distance to good dining and shopping!"
United States
Monica W.
The price is HK$3,893
HK$6,661 total
includes taxes & fees
5 Jan - 6 Jan
Cozy Cottage Perfect for Girls Night Away
Exterior
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.

Cottage in Frankfort

Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
10.0 out of 10, Exceptional, (37)
"Loved this quaint farmhouse cottage"
United States
Sandy F.
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Interior
11 Mi to Danville: Family Home in Lancaster

Cottage in Lancaster

11 Mi to Danville: Family Home in Lancaster
3.0 star property
11 Mi to Danville: Family Home in Lancaster
Interior
Spacious Frankfort Retreat on Bourbon Trail!

Cottage in Frankfort

Spacious Frankfort Retreat on Bourbon Trail!
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

3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
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

Capital City Cottage
8.6 out of 10, Excellent, (43)
"A cozy cottage nestled in the mountain that felt like home away from home. "
United States
Jena B.
The price is HK$779
HK$1,915 total
includes taxes & fees
13 Jan - 14 Jan
Capital City Cottage
Exterior
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Cottage in Lexington

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
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
Front of property
10 Mi to Keeneland: Family Home w/ Deck & Yard

Cottage in Lexington

10 Mi to Keeneland: Family Home w/ Deck & Yard
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

Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
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.
Outdoor spa tub
Twin Cottages **** Presale**** cottage #7

Cottage in Lawrenceburg

Twin Cottages **** Presale**** cottage #7
The price is HK$1,635
HK$3,090 total
includes taxes & fees
6 Jan - 7 Jan
Twin Cottages **** Presale**** cottage #7
Exterior
Springside BoHo Getaway

Cottage in Georgetown

Springside BoHo Getaway
9.8 out of 10, Exceptional, (55)
"Great place! We will stay here again. "
United States
Zeppelin F.
The price is HK$1,168
HK$2,421 total
includes taxes & fees
4 Jan - 5 Jan
Springside BoHo Getaway
Property grounds
Five Minutes from Keeneland!

Cottage in Versailles

Five Minutes from Keeneland!
10.0 out of 10, Exceptional, (23)
"The cottage was wonderful! Just what we needed and wanted. Jennifer is a great host and we will certainly stay again if the opportunity arises. "
United States
Matt T.
The price is HK$1,409
HK$2,514 total
includes taxes & fees
4 Jan - 5 Jan
Five Minutes from Keeneland!
Interior
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!

Cottage in Kenwick

Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
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

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
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
Interior
Our Lakeside Retreat w/ Deck on Lake Herrington!

Cottage in Lancaster

Our Lakeside Retreat w/ Deck on Lake Herrington!
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

Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants
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

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
10.0 out of 10, Exceptional, (14)
"Very clean place to stay. "
United States
Alisha F.
The price is HK$1,635
HK$2,778 total
includes taxes & fees
4 Jan - 5 Jan
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Front of property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!

Cottage in Georgetown

Georgetown Home ~ 6 Mi to Kentucky Horse Park!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very clean."
United States
Gabriel
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Interior
Lovely Lexington Home: 4 Mi to Downtown!

Cottage in Zandale

Lovely Lexington Home: 4 Mi to Downtown!
3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jessamine County Hotel Reviews

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Clean room, easy check-in/out, great location for our needs. "
Megan 1-night trip
Posted 19 hours ago
Elwood Hotel & Suites

Find out more about Jessamine County

Jessamine County Cottages information

Number of reviews
263
Accommodation
47 Cottages
Lowest Price
HK$1,915
Highest Price
HK$6,661

Explore a world of travel with Expedia