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.

Search Winchester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$271 nightly
The price is $299
Oct 25 - Oct 26
Total with taxes and fees
Plum Crazy: Frenchburg Cabin on 1 Acre
A building with a covered patio area, a small outdoor seating area, and a grassy lawn.

2. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (50 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
$158 nightly
The price is $174
Oct 27 - Oct 28
Total with taxes and fees
Mountaintop Cottage
A white house with a porch, stone wall, and a small garden.

3. 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)
"Good size kitchen and master bedroom...big tv..comfy couch...nice dining table...quiet and private."
United States
Lindi
$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 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.
$733 nightly
The price is $851
Oct 25 - Oct 26
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
Oct 25 - Oct 26
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Studio 6 Suites Lexington, Kentucky

Studio 6 Suites Lexington, Kentucky

8/10 Good
"It was just standard Motel 6. But, it was clean and comfortable. I was not pleased with the room being right next to the noisy highway. But, the heating system fan was so loud it helped to drown out the cars. I would have appreciated more info on how to work the TV. It was too complicated for my age group."
Chris 1-night trip
Posted less than an hour ago
Studio 6 Suites Lexington, Kentucky

Find out more about Winchester

Winchester Cottages information

Number of reviews
377
Accommodation
42 Cottages
Lowest Price
$174
Highest Price
$851

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.

Explore a world of travel with Expedia