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 $239

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Winchester cottages

Exterior

1. Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (44 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is CA $162
CA $239 total
includes taxes & fees
Sep 8 - Sep 9
Mountaintop Cottage
House (4 Bedrooms) | Interior

2. Walk to UK Campus: Charming Home w/ Patio!

Walk to UK Campus: Charming Home w/ Patio!
3.0 star property
Lexington
The price is CA $275
CA $752 total
includes taxes & fees
Sep 13 - Sep 14
Walk to UK Campus: Charming Home w/ Patio!
Interior

3. Cozy Cottage Perfect for Girls Night Away

Cozy Cottage Perfect for Girls Night Away
Lexington
10.0 out of 10, Exceptional, (16 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 $692
CA $1,193 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Cottage Perfect for Girls Night Away
House (1 Bedroom) | Interior

4. 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, (3 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 $208
CA $414 total
includes taxes & fees
Sep 9 - Sep 10
Plum Crazy: Frenchburg Cabin on 1 Acre
House (2 Bedrooms) | Interior

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 $446
CA $864 total
includes taxes & fees
Sep 9 - Sep 10
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

Natural Bridge State Resort Park

Natural Bridge State Resort Park

10/10 Excellent
"We went there for our 58th anniversary. The place fit right into the Red River Gorge area. The view of the trees from our room was beautiful. The room had a little musty smell but it seemed to fit the atmosphere of the area. From the dinning room you could watch the squirrels and birds enjoy the feeders The food and the staff were great! To sum it up the Lodge was not real fancy but just prefect for us"
Virginia 1-night trip
Posted 4 hours ago
Natural Bridge State Resort Park

Find out more about Winchester

Winchester Cottages information

Number of reviews
60
Accommodation
42 Cottages
Lowest Price
CA $239
Highest Price
CA $1,193

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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