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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Cottages in Winchester

Our top choices for Winchester cottages

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Interior

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
The price is S$338
includes taxes & fees
24 Aug - 25 Aug
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!
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!
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
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Georgetown Home ~ 6 Mi to Kentucky Horse Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very clean."
Georgetown Home ~ 6 Mi to Kentucky Horse Park!
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!
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!
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
10.0 out of 10, Exceptional, (1)
"I liked the porch and the pergola. My granddaughter ran around the house in bare feet and her feet got incredibly dirty. Floors probably need a good cleaning. That was the only begative i had."
10 Mi to Keeneland: Family Home w/ Deck & Yard
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!
Quaint Creekside Cottage w/ Porch & Backyard!
Private kitchen

Quaint Creekside Cottage w/ Porch & Backyard!

3.0 star property
Quaint Creekside Cottage w/ Porch & Backyard!
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!
Cozy Georgetown Cottage on a Working Horse Farm!
Interior

Cozy Georgetown Cottage on a Working Horse Farm!

3.0 star property
Cozy Georgetown Cottage on a Working Horse Farm!
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!
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!
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!
Hike & Fish: Nature Escape Near Licking River!
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Hike & Fish: Nature Escape Near Licking River!

3.0 star property
Hike & Fish: Nature Escape Near Licking River!
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!
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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Top Winchester Hotel Reviews

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"Pool was wonderful when open. Friendly staff great accommodations for the price "
Karen 2-night trip
Posted 12 hours ago
Natural Bridge State Resort Park

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.