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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Cottages in Winchester

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

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

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Private kitchen

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Quaint Creekside Cottage w/ Porch & Backyard!
Miscellaneous

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Dishwasher, paper towels

Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Lexington Home ~ 2 Mi to University of Kentucky!
Private kitchen

Lexington Home ~ 2 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 2 Mi to University of Kentucky!
Lexington Home ~ 5 Mi to University of Kentucky!
Private kitchen

Lexington Home ~ 5 Mi to University of Kentucky!

3.0 star property
Lexington Home ~ 5 Mi to University of Kentucky!
Gorgeous Lexington Retreat ~ 2 Mi From UK!
Fireplace

Gorgeous Lexington Retreat ~ 2 Mi From UK!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house is charming, extremely clean and comfy. The linens and access to helpful kitchen items is a bonus. The ease of booking and gaining access waa seamless. The only little thing was that the sofa bed was in the same room with queen bed. We didnt need to use it but if our other guest had joined the trip it would have been difficult. The king and queen beds are very comfy. "
Gorgeous Lexington Retreat ~ 2 Mi From UK!
Walk to UK Campus: Charming Home w/ Patio!
Interior

Walk to UK Campus: Charming Home w/ Patio!

3.0 star property
Walk to UK Campus: Charming Home w/ Patio!
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Interior

Hike & Climb: Pet-friendly Red River Gorge Cabin!

3.0 star property
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Lovely Lexington Home: 4 Mi to Downtown!
Terrace/patio

Lovely Lexington Home: 4 Mi to Downtown!

3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!
TV

Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!

3.0 star property
Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!
Lexington Family Home ~ 2 Miles to UK Campus!
Private kitchen

Lexington Family Home ~ 2 Miles to UK Campus!

3.0 star property
Lexington Family Home ~ 2 Miles to UK Campus!
Cozy Georgetown Cottage on a Working Horse Farm!
TV

Cozy Georgetown Cottage on a Working Horse Farm!

3.0 star property
Cozy Georgetown Cottage on a Working Horse Farm!
15 Mi to Dtwn Lexington: Serene Wilmore Home!
Interior

15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
15 Mi to Dtwn Lexington: Serene Wilmore Home!
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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Other property types in Winchester

Natural Bridge State Resort Park
Seasonal outdoor pool

Natural Bridge State Resort Park

3.5 star property
8.6 out of 10, Excellent, (1494)
"Friendly people, beautiful scenery and peaceful."
The price is S$127
includes taxes & fees
27 Feb - 28 Feb
Natural Bridge State Resort Park
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.

Frequently asked questions

Why book your cottage in Winchester with Expedia?
Expedia has some superb cottages in Winchester, so start planning for a memorable stay close to nature. If you have a budget, select how much you want to spend and the preferred star rating of your property. Or, make the most of our filters to search for cottages with a kitchen or a pool. We’ll help you find the right place whatever your plans or bank balance.
How can I find cheap cottages in Winchester?
Expedia is here to help you easily track down cheap cottages in Winchester. To reserve your special stay in a couple of quick clicks, try out the filter tool to refine your search by budget, star rating and amenities.
What is there to do in Winchester near my cottage?
The perfect travel accessory is a well-thought-out travel plan. Bluegrass Heritage Museum is a wonderful place to begin your exploration of Winchester.