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Our top choices for Winchester cottages

House (1 Bedroom) | Interior
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre

Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2)
"The cabin was adorable and had everything we needed for a weekend getaway. The host was very responsive, and we had a wonderful trip! "
United States
Anonymous traveler
$236 nightly
The price is $262
Dec 24 - Dec 25
Total with taxes and fees
Bring a Pet: Peaceful Frenchburg Cabin on 1 Acre
Exterior
Mountaintop Cottage

Mountaintop Cottage

Mountaintop Cottage
2.0 star property
Stanton
10.0 out of 10, Exceptional, (26)
"The cabin was in an excellent location and was very clean! The host was super helpful with providing directions and answering questions."
United States
Brandylynn M.
$177 nightly
The price is $195
Dec 25 - Dec 26
Total with taxes and fees
Mountaintop Cottage
Exterior
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland

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

Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
Lexington
10.0 out of 10, Exceptional, (285)
"Great visit "
United States
Titus M.
$201 nightly
The price is $233
Dec 27 - Dec 28
Total with taxes and fees
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
Exterior
Springside BoHo Getaway

Springside BoHo Getaway

Springside BoHo Getaway
Georgetown
9.8 out of 10, Exceptional, (55)
"Great place! We will stay here again. "
United States
Zeppelin F.
$282 nightly
The price is $311
Dec 30 - Dec 31
Total with taxes and fees
Springside BoHo Getaway
Interior
Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
10.0 out of 10, Exceptional, (14)
"This house is just as cute as the pictures with enough space for a large group. It’s also located within walking distance to good dining and shopping!"
United States
Monica W.
$737 nightly
The price is $855
Dec 24 - Dec 25
Total with taxes and fees
Cozy Cottage Perfect for Girls Night Away
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

Embassy Suites by Hilton Lexington Green

Embassy Suites by Hilton Lexington Green

10/10 Excellent
"The staff member was so friendly! She even gave my kids some baggies with activities in them for them to do!"
Stephanie 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Lexington Green

Find out more about Winchester

Winchester Cottages information

Number of reviews
379
Accommodation
34 Cottages
Lowest Price
$195
Highest Price
$855

Frequently asked questions

Why book your cottage in Winchester with Expedia?
We think that a vacation 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 favorite 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.

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