Lodging Image

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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

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, (298 reviews)
"The cottage was amazing! Everything we needed it had and the host is very attentive! We will definitely be back. "
United States
Brittany C.
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
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, (38 reviews)
"Great place to stay, with great views of the creek/river directly out the back door! Jon was a great host and responded to messages very quick. Definitely will stay again when up visiting family. "
United States
ben t.
Beautifully updated riverside 1840 cottage on the bourbon trail near Danville
Outdoor spa tub

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, (26 reviews)
"Great place! Owner was very accommodating. I highly recommend staying here!!"
United States
Jeff T.
Eire Cottage, Private Waterfall views, Hot tub. On Bourbon trail.
Exterior

Charming Tiny House on the Farm

Charming Tiny House on the Farm
Lancaster
10.0 out of 10, Exceptional, (1 review)
"Love this tiny house! So cute and in a nice location if you are looking for a few quiet days away. That’s why I picked this spot and it was perfect for some rest and relaxation."
United States
Rachel S.
Charming Tiny House on the Farm
Interior

Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
10.0 out of 10, Exceptional, (15 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 1,837
AED 3,125 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Cottage Perfect for Girls Night Away
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, (49 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, (9 reviews)
"Beautiful peaceful area .. everything was as stated !Would use again"
United States
Marie H.
3 bedroom cottage on horse farm close to Kentucky Horse Park, Keeneland, the Ark
Exterior

Capital City Cottage

Capital City Cottage
Frankfort
8.6 out of 10, Excellent, (46 reviews)
"We had a good experience here. Everything was clean and well prepared for us. The kitchen had all we needed and more. The donuts delivered on our last morning was a nice treat. "
United States
Tony G.
The price is AED 367
AED 886 total
includes taxes & fees
1 Jul - 2 Jul
Capital City Cottage
Exterior

Our Cottage is a perfect retreat for adults only in beautiful bluegrass region

Our Cottage is a perfect retreat for adults only in beautiful bluegrass region
Lexington
9.8 out of 10, Exceptional, (20 reviews)
"Excellent Stay!! "
United States
Malik R.
Our Cottage is a perfect retreat for adults only in beautiful bluegrass region
Exterior

1BD Modern Bourbon Cottage

1BD Modern Bourbon Cottage
Lawrenceburg
9.6 out of 10, Exceptional, (4 reviews)
"It was absolutely beautiful and such a wonderful place for a little get away! We will definitely we back!"
United States
Maddy W.
The price is AED 391
AED 1,034 total
includes taxes & fees
5 Jul - 6 Jul
1BD Modern Bourbon Cottage
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, (45 reviews)
"Quiet area and convenient to areas of interest. "
United States
chuck h.
Farmhouse Cottage local Horse farms, Distilleries, Winery Tours, walking trails.
Exterior

Springside BoHo Getaway

Springside BoHo Getaway
Georgetown
9.8 out of 10, Exceptional, (57 reviews)
"The place was perfect for our long weekend. Close to downtown and restaurants and a very comfortable and clean stay. "
United States
Amy P.
Springside BoHo Getaway
Exterior

Orchard Park cottage

Orchard Park cottage
Versailles
10.0 out of 10, Exceptional, (137 reviews)
"It was a very beautiful property, very conveniently located and comfortable"
United States
Kim S.
Orchard Park cottage
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, (3 reviews)
"House was super cute and very well maintained, We loved all of the specials details through out. The hot tub was a big hit. We would defiantly stay here again. The host was very informative and easy to communicate with. Overall this was a great place to stay!"
United States
Laurie D.
Location! Comfy Beds~Hot Tub~6mi KY Horse Park~Walkable
2 bedrooms, WiFi, bed sheets

Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants

Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants
Georgetown
9.4 out of 10, Exceptional, (3 reviews)
Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants
House (3 Bedrooms) | Front of property

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!
House (3 Bedrooms) | Front of property

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

Georgetown Home ~ 6 Mi to Kentucky Horse Park!
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very clean."
United States
Gabriel
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
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 1,178
AED 1,811 total
includes taxes & fees
2 Jul - 3 Jul
Bourbon Barrel Cottages #5 on Ky. Bourbon Trail
Exterior

Twin Cottages **** Presale**** cottage #7

Twin Cottages **** Presale**** cottage #7
Lawrenceburg
10.0 out of 10, Exceptional, (1 review)
"All of the above. All around great location private, clean, and nice. Angie the host was great and responsive. A little pricey with all the added fees but I would visit again "
United States
Valerie M.
The price is AED 1,263
AED 2,057 total
includes taxes & fees
1 Jul - 2 Jul
Twin Cottages **** Presale**** cottage #7
Exterior

Bourbon Barrel Cottages #3 on Ky. Bourbon Trail

Bourbon Barrel Cottages #3 on Ky. Bourbon Trail
Lawrenceburg
10.0 out of 10, Exceptional, (18 reviews)
"We really enjoyed our stay at the bourbon barrel cottage. Would highly recommend and will book again when we are in the area."
United States
Stephanie B.
The price is AED 1,178
AED 5,519 total
includes taxes & fees
5 Jul - 6 Jul
Bourbon Barrel Cottages #3 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.
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

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

10/10 Excellent
"Laura at the front desk was fantastic. It’s a very nice hotel and the service was amazing. Great pool and hot tub. Wonderful amenities like fire pits and bourbon dispensing machines."
BARBARA 1-night trip
Posted 10 hours ago
Marriott Lexington Griffin Gate Golf Resort & Spa