A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Winchester cottages

An outdoor patio with Adirondack chairs and a fire pit, surrounded by a forested area.

1. Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!

Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
3.0 star property
Luray
$290 nightly
The price is $334
Oct 21 - Oct 22
Total with taxes and fees
Luray 'black Walnut Cabin' on 2 Acres w/ Fire Pit!
A stone house with a white picket fence, a front porch, and potted plants.

2. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
$591 nightly
The price is $679
Oct 22 - Oct 23
Total with taxes and fees
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester

10/10 Excellent
"Everything was fantastic"
Dorothyann 1-night trip
Posted 4 hours ago
Fairfield Inn & Suites by Marriott Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
Accommodation
197 Cottages
Lowest Price
$334
Highest Price
$679

Frequently asked questions

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What is there to do in Winchester near my cottage?
Winchester has enough activities and sights to keep you on the hop for weeks, starting with Rock Harbor Golf Course. The Kernstown Battlefield, Museum of the Shenandoah Valley and Apple Blossom Mall are other fantastic attractions. If you're in town a while, Jim Barnett Park and Handley Regional Library are nice final touches to your itinerary.

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