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 Cottage Rentals from CA $244

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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
The price is CA $210
CA $419 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is CA $165
CA $244 total
includes taxes & fees
Oct 27 - Oct 28
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
The price is CA $208
CA $370 total
includes taxes & fees
Nov 1 - Nov 2
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.
The price is CA $700
CA $1,208 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is CA $451
CA $875 total
includes taxes & fees
Oct 25 - Oct 26
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

10/10 Excellent
"Modern, well decorated hotel near downtown. Cool design, more modern. Comfortable bed and room. Nice bathroom with nice toiletries. Minibar - thank you! Great restaurant and bar. Near a couple of music venues. Pay parking - all valet. Nothing cheap here, but well done and well run. Restaurant definitely worth a visit."
Robin 1-night trip
Posted less than an hour ago
The Manchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
377
Accommodation
42 Cottages
Lowest Price
CA $244
Highest Price
CA $1,208

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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