Search Winchester Cottage Rentals from CA $241

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Winchester cottages

House (1 Bedroom) | Interior

Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre

Hot Tub + Fire Pit: 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 traveller
The price is CA $169
CA $412 total
includes taxes & fees
May 25 - May 26
Hot Tub + Fire Pit: Frenchburg Cabin on 1 Acre
Exterior

Mountaintop Cottage

Mountaintop Cottage
Stanton
10.0 out of 10, Exceptional, (35 reviews)
"Great stay! Beautiful property and an awesome donkey"
United States
andymorg
The price is CA $163
CA $241 total
includes taxes & fees
May 26 - May 27
Mountaintop Cottage
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.
The price is CA $630
CA $1,093 total
includes taxes & fees
May 25 - May 26
Cozy Cottage Perfect for Girls Night Away
House (4 Bedrooms) | Interior

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 $236
CA $613 total
includes taxes & fees
May 28 - May 29
Walk to UK Campus: Charming Home w/ Patio!
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

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham

8/10 Good
"Cute place to stop for a night. Definitely was an exisiting hotel that was bought out and quickly flipped."
Samuel 1-night trip
Posted 2 hours ago
Hotel LEX, Trademark Collection by Wyndham

Find out more about Winchester

Winchester Cottages information

Number of reviews
37
Accommodation
38 Cottages
Lowest Price
CA $241
Highest Price
CA $1,093

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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