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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Featured Cottages in Winchester

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
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Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
The price is S$337
includes taxes & fees
20 Jul - 21 Jul
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Peaceful Mt Sterling Cabin: Deck & Fire Pit!
Outdoor dining

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

3.0 star property
Lexington Getaway w/ Backyard Deck < 2 Mi to UK!
10 Mi to Keeneland: Family Home w/ Deck & Yard
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10 Mi to Keeneland: Family Home w/ Deck & Yard

3.0 star property
10 Mi to Keeneland: Family Home w/ Deck & Yard
Quaint Creekside Cottage w/ Porch & Backyard!
Private kitchen

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
Lexington Home ~ 2 Mi to University of Kentucky!
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Lexington Home ~ 2 Mi to University of Kentucky!

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

3.0 star property
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
Hike & Climb: Pet-friendly Red River Gorge Cabin!
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Hike & Climb: Pet-friendly Red River Gorge Cabin!

3.0 star property
Hike & Climb: Pet-friendly Red River Gorge Cabin!
Family Home w/ Ping-pong & Fire Pit in Lexington
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Family Home w/ Ping-pong & Fire Pit in Lexington

3.0 star property
Family Home w/ Ping-pong & Fire Pit in Lexington
Walk to UK Campus: Charming Home w/ Patio!
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Walk to UK Campus: Charming Home w/ Patio!

3.0 star property
Walk to UK Campus: Charming Home w/ Patio!
Lovely Lexington Home: 4 Mi to Downtown!
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Lovely Lexington Home: 4 Mi to Downtown!

3.0 star property
Lovely Lexington Home: 4 Mi to Downtown!
Cozy Georgetown Cottage on a Working Horse Farm!
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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!
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15 Mi to Dtwn Lexington: Serene Wilmore Home!

3.0 star property
15 Mi to Dtwn Lexington: Serene Wilmore Home!
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!
Historic & Spacious Family Home in Nicholasville!
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Historic & Spacious Family Home in Nicholasville!

3.0 star property
Historic & Spacious Family Home in Nicholasville!
Cozy Cabin w/ Hot Tub in Heart of Red River Gorge!
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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!
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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Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that a holiday should be simple, so if you're after cottages in Winchester at a nice price, Expedia has your back. Keep the budget under control and opt for a low-cost option far away from the hustle and bustle, or splurge on an upmarket cottage to pamper your favourite people.
How can I find cheap cottages in Winchester?
With Expedia's useful filter tool, sourcing cheap cottages in Winchester couldn't be simpler. To discover properties that'll make your wallet smile, narrow your search by budget, amenities and star rating.
What is there to do in Winchester near my cottage?
The most useful travel accessory is a well-planned schedule. Southwind Golf Course is a good spot to start your adventures in Winchester.