Hotels in Winchester

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Where to stay in Winchester?

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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Our prices for Winchester are cheapest in January

See average prices and weather for all months
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
View properties in August

Month selector

Currently viewing crowd sizes and weather for August.
Weather forecast for Winchester
August
trending_upHigh crowds
High 29°C / low 18°C. Sunny most days.
View properties in August
29°
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August, High crowds, average high temperature 29 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
25°
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September, Moderate crowds, average high temperature 25 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
18°
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October, High crowds, average high temperature 18 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
11°
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November, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature 2 degrees Celsius. Sunny most days.
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December, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
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January, Low crowds, average high temperature 4 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
-4°
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February, Low crowds, average high temperature 6 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
11°
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March, Low crowds, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Partly sunny.
17°
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April, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
22°
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May, High crowds, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
27°
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June, Moderate crowds, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
16°
30°
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July, High crowds, average high temperature 30 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
Monthly weather averages (˚C)

Top neighborhoods in Winchester

Old Town Winchester map

Old Town Winchester

Winchester's Old Town Winchester neighborhood is known for its restaurants and bars, and entices visitors with attractions including Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District map

Winchester Historic District

Winchester's Winchester Historic District neighborhood is home to attractions such as Bright Box Theater and Winchester Little Theater.

Top landmarks in Winchester

Winchester and related destinations

Immerse yourself in history at Stonewall Jackson's Headquarters and the Museum of the Shenandoah Valley. Catch a show at Bright Box Theater, then explore the charming pedestrian mall filled with excellent restaurants and shops.

Top traveler reviews of Winchester

Check out reviews of Winchester hotels guests love

Frequently asked questions

What hotels do travelers like in Winchester?
Can I book a refundable hotel in Winchester?
If you're looking for the flexibility to change your travel plans to Winchester, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where should I stay in Winchester if I'm looking for a budget-friendly accommodation?
Where can I stay in Winchester if I want a vacation home instead of a hotel?
If you're looking for a good alternative to a hotel, review our selection of 19 vacation homes. In addition, you can choose from 21 apartments.
What will the weather in Winchester be like during my visit?
July and August are typically the warmest months in Winchester when the average temp is 72°F. January and February are the coldest months when the average temperature is 36°F. May and September are the months with the most rain.
Why should I book my Winchester accommodation with Hotels.com?
There are lots of reasons to book your Winchester trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.