Hotels in Winchester

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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

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Currently viewing crowd sizes and weather for August.
Weather forecast for Winchester
August
trending_upHigh crowds
High 86°F / low 67°F. Sunny most days.
View properties in August
86°
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August, High crowds, average high temperature 86 degrees Fahrenheit, average low temperature 67 degrees Fahrenheit. Sunny most days.
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81°
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September, Moderate crowds, average high temperature 81 degrees Fahrenheit, average low temperature 62 degrees Fahrenheit. Sunny most days.
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71°
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October, Low crowds, average high temperature 71 degrees Fahrenheit, average low temperature 51 degrees Fahrenheit. Sunny most days.
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58°
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November, Low crowds, average high temperature 58 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Sunny most days.
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51°
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December, Moderate crowds, average high temperature 51 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Partly sunny.
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46°
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January, Low crowds, average high temperature 46 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Cloudy most days.
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51°
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February, Low crowds, average high temperature 51 degrees Fahrenheit, average low temperature 35 degrees Fahrenheit. Cloudy most days.
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60°
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March, Moderate crowds, average high temperature 60 degrees Fahrenheit, average low temperature 42 degrees Fahrenheit. Sunny most days.
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69°
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April, Moderate crowds, average high temperature 69 degrees Fahrenheit, average low temperature 48 degrees Fahrenheit. Sunny most days.
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77°
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May, High crowds, average high temperature 77 degrees Fahrenheit, average low temperature 57 degrees Fahrenheit. Sunny most days.
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85°
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June, High crowds, average high temperature 85 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
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87°
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July, High crowds, average high temperature 87 degrees Fahrenheit, average low temperature 68 degrees Fahrenheit. Sunny most days.
68°
Monthly weather averages (˚F)

Top landmarks in Winchester

Learn more about Winchester

Explore the historic town square, where antique shops and local eateries offer a taste of small-town Southern life. Venture to nearby Tims Ford State Park for boating, fishing, and hiking along scenic lakeside trails.

Check out reviews of Winchester hotels guests love

Frequently asked questions

How much does a hotel room cost in Winchester?
You can discover great hotels in Winchester from $64 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Winchester that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How can I find deals and earn rewards at Winchester hotels?
Discover great deals on Winchester hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. If it's a spontaneous trip, check out our last-minute deals on Winchester hotels.
Can I book Winchester hotels with free cancellation?
It's easy to book a refundable Winchester hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best Winchester hotels with free parking?
If you're exploring by car, finding a great Winchester hotel with free parking is a win. Our travelers' favorites include:
Are all taxes and fees included in the Winchester hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
What hotels do travelers like in Winchester?
Best Western Inn is a property that our guests really like.
Where can I get free parking at my hotel in Winchester?
Best Western Inn offers the perk of free parking.
Can I book refundable hotels in Winchester?
If you want the flexibility to change your travel plans to Winchester, most accommodations provide refundable* rates you can book. You can see 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 want a reasonably priced accommodation?
Best Western Inn is an accommodation you might want to consider that'll save you money.
Where can I stay in Winchester if I want a vacation home instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 115 vacation homes. You can also consider one of the 6 apartments or 13 cottages.
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 74°F. January and February are the coldest months when the average temperature is 43°F. March and April are the months with the most rain.
Why should I book my Winchester hotel through 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.

Find out more about Winchester

Find out more about Winchester

If you're looking for a place to get away, look no further than Winchester. Whether you're planning to stay for a night or for the week, the area around Winchester has accommodations to fit every need. Search for hotels in Winchester with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Winchester hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Winchester hotel deals are here with our lowest price guarantee.