Winchester Cottages

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Cottages in Winchester

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

Lexington KY

With a stay at this cottage, you'll be centrally located in Lexington, within a 15-minute drive of University of Kentucky and Lexington Convention Center.

Mountaintop Cottage

Stanton KY

$172 nightly

$189 total

Jun 16 - Jun 17

Total with taxes and fees

With a stay at this cottage in Stanton, you'll be in the mountains, and 16.7 mi (26.8 km) from Natural Bridge State Park and 16.8 mi (27 km) from Red River Gorge Geological Area.

Cozy 1 bedroom cottage on picturesque horse farm

Georgetown KY

Located in Georgetown, this cottage is in a rural location, a 4-minute drive from Country Boy Brewing and 6 minutes from Toyota Visitor Center.

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

Lexington KY

Located in Lexington, this cottage is in a rural location, a 4-minute drive from Boone Station State Historic Site and 6 minutes from Lexington Sporting Club Youth Complex.

Cozy Cottage Perfect for Girls Night Away

Lexington KY

With a stay at this cottage in Lexington, you'll be within a 5-minute drive of University of Kentucky and Lexington Convention Center.

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

Georgetown KY

With a stay at this cottage, you'll be centrally located in Georgetown, within a 10-minute drive of Kentucky Horse Park and Georgetown College.

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

Georgetown KY

With a stay at this cottage in Georgetown, you'll be within a 10-minute drive of Kentucky Horse Park and Georgetown College.

1 bed cottage, grill, fire pit, Very close to Red River Gorge!!

Stanton KY

Located in Stanton, this cottage is within a 15-minute drive of Kentucky Reptile Zoo and Osborne Bend Trail.

Pet friendly

Air conditioning

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Frenchburg KY

$308 nightly

$339 total

Jun 16 - Jun 17

Total with taxes and fees

With a stay at this cottage in Frenchburg, you'll be 17.4 mi (28 km) from Red River Gorge Geological Area and 25.6 mi (41.3 km) from Natural Bridge State Park.

Springside BoHo Getaway

Georgetown KY

With a stay at this cottage, you'll be centrally located in Georgetown, within a 10-minute drive of Kentucky Horse Park and Georgetown Scott County Museum.

Cottage In Downtown Georgetown Within Walking Distance Of Shops and Restaurants

Georgetown KY

With a stay at this cottage in Georgetown, you'll be within a 10-minute drive of Kentucky Horse Park and Georgetown College.

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

Mount Sterling KY

With a stay at this cottage in Mount Sterling, you'll be within a 10-minute drive of Mount Sterling Library and Gateway Regional Arts Center.

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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.