Hotels in Winchester

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Check prices for these dates

Tonight
May 17 - May 18
Tomorrow
May 18 - May 19
Next weekend
May 23 - May 25
In two weeks
May 30 - Jun 1

Where to stay in Winchester?

Best Western Inn
Suite, 1 King Bed, Non Smoking, Jetted Tub (Oversized Room) | Desk, laptop workspace, blackout drapes, iron/ironing board

Best Western Inn

2.5 star property
8.8 out of 10, Excellent, (601)
$110 nightly
The price is $125
May 21 - May 22
Total includes taxes and fees
Best Western Inn
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.
trending_down

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
May
$152
Average price during May is $152
Jun
$224
Average price during June is $224
Jul
$159
Average price during July is $159
Aug
$168
Average price during August is $168
Sep
$150
Average price during September is $150
Oct
$159
Average price during October is $159
Nov
$128
Average price during November is $128
Dec
$133
Average price during December is $133
Jan
$115
Average price during January is $115
Feb
$118
Average price during February is $118
Mar
$128
Average price during March is $128
Apr
$137
Average price during April is $137
Currently viewing crowd sizes and weather for May.

May

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

Tim's Ford Marina

If thrills are what you're after, head to Tim's Ford Marina, located 7.9 mi (12.7 km) from central Winchester. If you have fun at Tim's Ford Marina, you'll love Lakeview Marina, located nearby.

See properties in Tim's Ford Marina
Tim's Ford Marina

Learn more about Winchester

Winchester is well-known for its attractions such as Twin Creeks Marina and Tim's Ford Marina. This welcoming city has something for everyone including sights like Tims Ford State Park and Tims Ford.

See all hotels in Winchester
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

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 can I stay with my pet in Winchester?
Your furry friend can stay with you at these pet-friendly hotels: Best Western Inn and Spectacular views and location on Tim’s Ford Lake!.
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 119 vacation homes. You can also consider one of the 6 apartments or 13 cottages.
Where can I stay if I'm visiting Winchester with my kids?
Parents traveling with children may want to consider Best Western Inn, Spectacular views and location on Tim’s Ford Lake! and Tims Ford Lake! Modern farmhouse right across street from State Park.
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.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

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