Cottages in Jessamine County
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A bridge over a river with surrounding trees and a small settlement.

Cottages in Jessamine County

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your current months are November, 2026 and December, 2026.

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Top cities in Jessamine County

A town with a prominent clock tower, intersecting roads, and surrounding residential buildings.

Nicholasville

A bridge over a calm river with a sunset reflection.

Wilmore

Find holiday rentals that suit your style

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Cottages

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Our top choices for Jessamine County cottages

A wooden deck overlooking a river, surrounded by dense greenery.

A kitchen with wooden cabinets, a marble countertop, a stainless steel refrigerator, and a window with patterned curtains.

A wooden interior with large windows, a table with a pitcher, and a chair.

A wooden cabin interior with large windows, a dining table, a white wicker sofa, and a red patterned rug.

1. 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, (2 reviews)

10/10

Exceptional

(2 reviews)

"We enjoyed everything about the property "

Jessica

Our Lakeside Retreat w/ Deck on Lake Herrington!

A single-story brick house with a front porch, a small attached garage, and a well-maintained lawn.

A kitchen with a refrigerator, microwave, dishwasher, wooden dining table with chairs, and a window with blinds.

A living room with a fireplace, a sofa, a coffee table, and a rug.

A living room with a fireplace, a television, a sofa, and a coffee table.

2. Lexington Home ~ 2 Mi to University of Kentucky!

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property

Open Gates

Lexington Home ~ 2 Mi to University of Kentucky!

A porch with two Adirondack chairs and a concrete floor.

A kitchen with a wooden bar stool area, a dishwasher, and a window with patterned curtains.

A bedroom with a four-poster bed, a nightstand with drawers, a lamp, a chair, and a window with blinds.

A stone gate with a plaque, surrounded by autumn foliage and a stone wall.

3. Peaceful Bluegrass Getaway on 10-acre Farm!

Peaceful Bluegrass Getaway on 10-acre Farm!

3.0 star property

Harrodsburg

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Peaceful and simple. The beds were all very comfortable, great kitchen with everything you need, and a beautiful backyard. The hosts were very communicative and recommended a great place for a Friday night dinner. Our stay exceeded my expectations. "

Crystal

Peaceful Bluegrass Getaway on 10-acre Farm!

A single-story brick house with a chimney, a patio with two chairs and a grill, and a small tree in a purple pot.

A modern kitchen with a marble countertop, stainless steel appliances, and a central island with bar stools.

A bathroom with two sinks, a mirror, a shower, and a window.

A spacious dining area with a wooden table set for four, surrounded by wooden chairs. A chandelier hangs above, and the room has a modern kitchen in the background.

4. 11 Mi to Danville: Family Home in Lancaster

11 Mi to Danville: Family Home in Lancaster

3.0 star property

Lancaster

11 Mi to Danville: Family Home in Lancaster

A two-story house with a red brick facade, a white garage door, and a front yard with a lawn and trees.

A modern living room with a sectional sofa, a leather recliner, a wooden coffee table, and a small side table with a plant.

A spacious living room with a fireplace, a large sofa, a coffee table, and a television mounted above the fireplace.

A hallway with a bench, a white door, and two vases with plants.

5. Spacious Frankfort Retreat on Bourbon Trail!

Spacious Frankfort Retreat on Bourbon Trail!

3.0 star property

Frankfort

Spacious Frankfort Retreat on Bourbon Trail!

A brick house with a dark front door, a chimney, and a small front yard with a pathway leading to the door.

A kitchen with a marble countertop, bar stools, a chandelier, and a wooden cabinet.

A living room with a fireplace, a television mounted above it, and a ceiling fan.

A spacious living room with a large dining table, elegant wooden chairs, a chandelier, and a fireplace.

6. Walk to UK Campus: Charming Home w/ Patio!

Walk to UK Campus: Charming Home w/ Patio!

3.0 star property

Seven Parks

Walk to UK Campus: Charming Home w/ Patio!

A covered patio with two metal chairs and a small table, surrounded by a wooden pergola, set against a backdrop of a lush green park.

A living room with a sectional sofa, a fireplace, a ceiling fan, and a large window.

A living room with a sectional sofa, a coffee table, two side tables with lamps, a ceiling fan, and large windows with curtains.

A walk-in closet with metal shelves, a wooden rack, and a door.

7. 'blue Moon Cottage' w/ Amazing Views of 5 Counties

'blue Moon Cottage' w/ Amazing Views of 5 Counties

3.0 star property

Danville

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"House and property were immaculate and so welcoming. Beautiful location and views, quietly tucked away. We felt very at home. Will definitely stay there again! Host was so helpful and kind. "

Caryn

'blue Moon Cottage' w/ Amazing Views of 5 Counties

A wooden deck with a metal safety mat, surrounded by lush green trees and a wooden fence.

A living room with two sofas, a coffee table, and framed pictures on the wall.

A residential house with a garage, brick exterior, and a front porch with potted plants.

8. Family Home w/ Ping-pong & Fire Pit in Lexington

Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property

Lexington

Family Home w/ Ping-pong & Fire Pit in Lexington

A single-story house with a front porch, a small deck, and a covered outdoor seating area.

A bathroom with two sinks, a toilet, a shower, a large mirror, and shelves with plants.

A modern kitchen with stainless steel appliances, dark cabinetry, and a granite countertop.

A modern kitchen with a central island, dining area with chairs, and a large window with a view.

9. Green Lantern: Game Room, Furnished Deck, Modern

Green Lantern: Game Room, Furnished Deck, Modern

3.0 star property

Eastland Parkway

Green Lantern: Game Room, Furnished Deck, Modern

A balcony with wicker furniture, a round table, and a view of a river and trees.

A spacious living room with a large flat-screen TV, leather armchair, and a sofa.

A modern bathroom with a large mirror, white tiles, a sink, and a potted plant.

A dining area with a long wooden table set for six, surrounded by chairs, with a brick fireplace and large windows.

10. Herrington Lake Retreat w/ Dock, 1 Mi to Marina!

Herrington Lake Retreat w/ Dock, 1 Mi to Marina!

3.0 star property

Harrodsburg

Herrington Lake Retreat w/ Dock, 1 Mi to Marina!

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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Hotels near Baptist Health Lexington
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B&B in Berea
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Cottages in Casey County
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Downtown Lexington Hotels
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Hotels with free breakfast in Georgetown
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Georgetown Hotels
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Cottages in Harrison County
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Hostels in Kentucky
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Treehouses in Kentucky
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Lancaster Hotels
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Romantic Hotels in Lexington
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Lexington Hotels
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Cabin Rentals in Montgomery County
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Motel 6 Hotels in Richmond
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Cabin Rentals in Rockcastle County
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Hotels near Woodford Reserve Distillery
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Flights to Salvisa
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Flights from Albuquerque (ABQ) to Lexington (LEX)
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Flights from Abuja (ABV) to Lexington (LEX)
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Flights from Abha (AHB) to Lexington (LEX)
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Flights from Athens (AHN) to Lexington (LEX)
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Flights from Al-Jawf Regional Airport (AJF) to Lexington (LEX)
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Flights from Alicante (ALC) to Lexington (LEX)
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Flights from Andenes (ANX) to Lexington (LEX)
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Flights from Paso de los Libres (AOL) to Lexington (LEX)
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Flights from St. George's (BDA) to Lexington (LEX)
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Flights from Binghamton (BGM) to Lexington (LEX)
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Flights from Hancock (CMX) to Lexington (LEX)
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Flights from Phoenix (DVT) to Lexington (LEX)
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Flights from Labuan (LBU) to Lexington (LEX)
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Flights from Liege (LGG) to Lexington (LEX)
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Flights from Managua (MGA) to Lexington (LEX)
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Flights from Montgomery (MGM) to Lexington (LEX)
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Flights from Marinduque Island (MRQ) to Lexington (LEX)
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Flights from Minsk (MSQ) to Lexington (LEX)
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Flights from Maun (MUB) to Lexington (LEX)
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Flights from Negril (NEG) to Lexington (LEX)
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Flights from Noosa (NSA) to Lexington (LEX)
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Flights from Oklahoma City (OKC) to Lexington (LEX)
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Flights from Chicago (ORD) to Lexington (LEX)
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Flights from Panama City (PAC) to Lexington (LEX)
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Flights from Porto Alegre (POA) to Lexington (LEX)
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Flights from Pula (PUY) to Lexington (LEX)
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Flights from Salerno (QSR) to Lexington (LEX)
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Flights from Knoxville (TYS) to Lexington (LEX)
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Flights from Charleville Mezieres (XCZ) to Lexington (LEX)
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Flights from Abbotsford (YXX) to Lexington (LEX)
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Flights from Sarnia (YZR) to Lexington (LEX)
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Burgin Holidays
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Headley-Whitney Museum
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Jd Legends Bar & Grill
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Keene Trace Golf Club
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Kentucky Horse Park
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Lexington Memorial Coliseum
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Lexington Holidays
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Lovers Leap Vineyards and Winery
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Mary Todd Lincoln House
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Mill Ridge Farm
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Paradise Cove Aquatic Center
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Rising Sons Home Farm Winery
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Stanford Holidays
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The American Saddlebred Museum
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Versailles Holidays
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Car hire near Woodford Reserve Distillery
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Cottages in Jessamine County

Change your mind

Treat yourself

Be picky

Top cities in Jessamine County

Nicholasville

Wilmore

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Jessamine County cottages

1. Our Lakeside Retreat w/ Deck on Lake Herrington!

2. Lexington Home ~ 2 Mi to University of Kentucky!

3. Peaceful Bluegrass Getaway on 10-acre Farm!

4. 11 Mi to Danville: Family Home in Lancaster

5. Spacious Frankfort Retreat on Bourbon Trail!

6. Walk to UK Campus: Charming Home w/ Patio!

7. 'blue Moon Cottage' w/ Amazing Views of 5 Counties

8. Family Home w/ Ping-pong & Fire Pit in Lexington

9. Green Lantern: Game Room, Furnished Deck, Modern

10. Herrington Lake Retreat w/ Dock, 1 Mi to Marina!

Explore a world of travel with Expedia