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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winchester cottages

A hot tub with a wooden deck and a wooden fence.

1. 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, (4 reviews)
"This cabin was 100% the cleanest and nicest I’ve ever stayed in. Adorable, had everything needed for a comfortable stay. "
United States
Amy
$302 nightly
The price is $333
Nov 1 - Nov 2
Total with taxes and fees
Plum Crazy: Frenchburg Cabin on 1 Acre
A white house with a porch, stone wall, and a small garden.

2. 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, (306 reviews)
"The hosts were very attentive to our needs and made sure we had a happy stay. Would recommend them to anyone and would stay here again."
United States
Alicia C.
$225 nightly
The price is $261
Nov 1 - Nov 2
Total with taxes and fees
Charming Farm Cottage view Horses + City Access - Near Bourbon Trail Keeneland
A building with a covered patio area, a small outdoor seating area, and a grassy lawn.

3. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (50 reviews)
"House is great, very comfortable and clean. Owners are very friendly and responsive."
United States
Mike P.
$158 nightly
The price is $174
Nov 2 - Nov 3
Total with taxes and fees
Mountaintop Cottage
A bathroom with a pink wall, a gold-framed mirror, a white light switch, a bottle of wine, and a glass on a white countertop.

4. Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
9.8 out of 10, Exceptional, (17 reviews)
"This property was perfect for our weekend girls trip! We had plenty of space upstairs in the slumber party room for our children. Each room was decorated so cute! We enjoyed having the utensils needed to cook breakfast on this trip as well. Would recommend and stay again!"
United States
Hali B.
$735 nightly
The price is $853
Nov 3 - Nov 4
Total with taxes and fees
Cozy Cottage Perfect for Girls Night Away
A wooden cabin with a pitched roof, a front door, a small porch, and a swing seat.

5. 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
Nov 1 - Nov 2
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

Elwood Hotel & Suites

Elwood Hotel & Suites

10/10 Excellent
"Super cute and clean spot near the hospital! 🙏❤️"
Sheetal 1-night trip
Posted 2 hours ago
Elwood Hotel & Suites

Find out more about Winchester

Winchester Cottages information

Number of reviews
377
Accommodation
42 Cottages
Lowest Price
$174
Highest Price
$853

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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