Cottages in Jessamine County

Compare and save

  • 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

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Jessamine County cottages

Exterior

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, (290 reviews)
"Great visit "
United States
Titus M.
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
Terrace/patio

8 min to Buffalo Trace, walk to Capital Charming 3-bedroom cottage in Frankfort.

8 min to Buffalo Trace, walk to Capital Charming 3-bedroom cottage in Frankfort.
Frankfort
8 min to Buffalo Trace, walk to Capital Charming 3-bedroom cottage in Frankfort.
Exterior

Springside BoHo Getaway

Springside BoHo Getaway
Georgetown
9.8 out of 10, Exceptional, (56 reviews)
"Great property in a great location!"
United States
Brent and Tonya R.
Springside BoHo Getaway
Exterior

Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.

Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Frankfort
9.8 out of 10, Exceptional, (39 reviews)
"We wanted a quiet rural place that had ready driving access to distilleries, and this was great"
United States
Fr. David J. V.
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Property grounds

Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.

Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Frankfort
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful property and owners."
United States
Karen M.
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Exterior

Capital City Cottage

Capital City Cottage
Frankfort
8.6 out of 10, Excellent, (43 reviews)
"A cozy cottage nestled in the mountain that felt like home away from home. "
United States
Jena B.
The price is AED 367
AED 916 total
includes taxes & fees
29 Mar - 30 Mar
Capital City Cottage
Interior

Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
10.0 out of 10, Exceptional, (14 reviews)
"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 AED 1,388
AED 2,571 total
includes taxes & fees
20 Apr - 21 Apr
Cozy Cottage Perfect for Girls Night Away
Outdoor dining

Beautifully updated riverside 1840 cottage on the bourbon trail near Danville

Beautifully updated riverside 1840 cottage on the bourbon trail near Danville
Perryville
10.0 out of 10, Exceptional, (32 reviews)
"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
Exterior

Orchard Park cottage

Orchard Park cottage
Versailles
10.0 out of 10, Exceptional, (131 reviews)
"It was a very beautiful property, very conveniently located and comfortable"
United States
Kim S.
Orchard Park cottage
Outdoor dining

Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!

Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!
Midway
10.0 out of 10, Exceptional, (48 reviews)
"Host was very helpful and addressed any concerns. Great location and the home feels brand new. Great comfortable beds and nice bathrooms. "
United States
Liz T.
Discover Your Perfect Getaway: Cottage in the Heart of Horse & Bourbon Country!
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Georgetown
10.0 out of 10, Exceptional, (4 reviews)
"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

Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.

Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.
Paris
10.0 out of 10, Exceptional, (3 reviews)
"Well cared for, clean and friendly "
United States
Kerry F.
Charming 3-bedroom detached cottage on horse farm near Lexington and Georgetown.
Property grounds

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.
Five Minutes from Keeneland!
Exterior

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail

Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (14 reviews)
"Very clean place to stay. "
United States
Alisha F.
The price is AED 1,026
AED 1,609 total
includes taxes & fees
5 Apr - 6 Apr
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
House (3 Bedrooms) | Interior

Our Lakeside Retreat w/ Deck on Lake Herrington!

Our Lakeside Retreat w/ Deck on Lake Herrington!
3.0 star property
Lancaster
10.0 out of 10, Exceptional, (1 review)
"We enjoyed everything about the property "
United States
Jessica
Our Lakeside Retreat w/ Deck on Lake Herrington!
Terrace/patio

1BD Modern Bourbon Cottage

1BD Modern Bourbon Cottage
Lawrenceburg
10.0 out of 10, Exceptional, (1 review)
"Receptiveness and availability of hostess to a small handful of concerns. Beauty of the rental unit itself and the view of the Courthouse (made famous in a sixties Hollywood production, "The Flim Flam Man). A part of Kentucky you might drive through bit rarely drive to. Really glad I took the time to do so in this lovely and welcoming stopping point on the Bourbon Trail."
United States
Amye B.
The price is AED 366
AED 999 total
includes taxes & fees
5 Apr - 6 Apr
1BD Modern Bourbon Cottage
Exterior

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY

Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Lexington
10.0 out of 10, Exceptional, (17 reviews)
"Great location to Keeneland, Distillery’s, great dining……darling gated property with front porch and fire pit for cozy nights! Listed as 2 bedroom, but one has a day bed. "
United States
Rebecca M.
Cottage is located on scenic byway in beautiful bluegrass region of Lexington KY
Outdoor dining

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable

Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Georgetown
10.0 out of 10, Exceptional, (2 reviews)
"Very nice! Loved it and would definitely book again! "
United States
Senia E.
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
Exterior

Peaceful Lakeside Cabin with Campsite Access Nature Lover’s Getaway in Stanford

Peaceful Lakeside Cabin with Campsite Access Nature Lover’s Getaway in Stanford
Stanford
10.0 out of 10, Exceptional, (1 review)
"Clean and convenient for fishing at the lake "
United States
Patrick T.
Peaceful Lakeside Cabin with Campsite Access Nature Lover’s Getaway in Stanford
House (3 Bedrooms) | Front of property

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

10 Mi to Keeneland: Family Home w/ Deck & Yard
3.0 star property
Lexington
10.0 out of 10, Exceptional, (1 review)
"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
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

Fairfield Inn & Suites by Marriott Lexington North

Fairfield Inn & Suites by Marriott Lexington North

8/10 Good
"We didn’t stay for breakfast. I do have a huge complaint about the shower. The curtain was too short so when you took a shower it let water spill out. It made quite a mess and was a hazard because of the wet floor. The shower faucet looked liked it was ready to fall off."
Jeanne 1-night trip
Posted 1 hour ago
Fairfield Inn & Suites by Marriott Lexington North