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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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Winchester cottages

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
$172 nightly
The price is $189
Jul 20 - Jul 21
Total with taxes and fees
Mountaintop Cottage
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 traveler
$262 nightly
The price is $289
Jul 20 - Jul 21
Total with taxes and fees
Plum Crazy: Frenchburg Cabin on 1 Acre
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.
$733 nightly
The price is $851
Jul 21 - Jul 22
Total with taxes and fees
Cozy Cottage Perfect for Girls Night Away
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
$567 nightly
The price is $625
Jul 20 - Jul 21
Total with taxes and fees
Ridgefolk Retreats! Set of 2 Cabins in Frenchburg
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

The Manchester

The Manchester

8/10 Good
"Really cool building and super welcoming, helpful staff. However, not great sound barrier between rooms."
Michael 1-night trip
Posted less than an hour ago
The Manchester

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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