An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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Our top choices for Winchester cottages

House (2 Bedrooms) | Interior

Ridgefolk Retreats! Set of 2 Cabins in Frenchburg

Ridgefolk Retreats! Set of 2 Cabins in Frenchburg
3.0 star property
Frenchburg
The price is CA $452
CA $877 total
includes taxes & fees
Jul 29 - Jul 30
Ridgefolk Retreats! Set of 2 Cabins in Frenchburg
Exterior

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (39 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is CA $183
CA $264 total
includes taxes & fees
Jul 30 - Jul 31
Mountaintop Cottage
Interior

Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
10.0 out of 10, Exceptional, (15 reviews)
"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.
The price is CA $702
CA $1,211 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Cottage Perfect for Girls Night Away
House (1 Bedroom) | Interior

Plum Crazy: Frenchburg Cabin on 1 Acre

Plum Crazy: Frenchburg Cabin on 1 Acre
3.0 star property
Frenchburg
10.0 out of 10, Exceptional, (2 reviews)
"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 traveller
The price is CA $198
CA $406 total
includes taxes & fees
Jul 29 - Jul 30
Plum Crazy: Frenchburg Cabin on 1 Acre
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

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

8/10 Good
"The toilet stopped up first time using it. Our WiFi didn’t work and when I sent a text, no one answered it."
Terri 1-night trip
Posted less than an hour ago
DoubleTree Suites by Hilton Hotel Lexington

Find out more about Winchester

Winchester Cottages information

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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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