Photo by Hyelsinta

Hotels in Winchester

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Check prices for these dates

Tonight
May 7 - May 8
Tomorrow
May 8 - May 9
This weekend
May 9 - May 11
Next weekend
May 16 - May 18

Where to stay in Winchester?

Holiday Inn Express Lexington East - Winchester by IHG
In-room safe, desk, laptop workspace, blackout drapes

Holiday Inn Express Lexington East - Winchester by IHG

2.5 star property
9.4 out of 10, Exceptional, (447)
The price is $119
includes taxes & fees
$107 per night
May 18 - May 19
Holiday Inn Express Lexington East - Winchester by IHG
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 hotels in Winchester are cheapest in December

See average prices and weather for all months

Price trends for hotels in Winchester

Pricing is based on two traveler single night rates
May
$131
Average price during May is $131
Jun
$128
Average price during June is $128
Jul
$117
Average price during July is $117
Aug
$117
Average price during August is $117
Sep
$115
Average price during September is $115
Oct
$120
Average price during October is $120
Nov
$103
Average price during November is $103
Dec
$94
Average price during December is $94
Jan
$96
Average price during January is $96
Feb
$98
Average price during February is $98
Mar
$115
Average price during March is $115
Apr
$118
Average price during April is $118
Currently viewing crowd sizes and weather for May.

May

trending_upHigh crowds
High 74°F / low 56°F. Sunny most days.
74°
weather_sun
May, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
82°
weather_sun
June, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 63 degrees Fahrenheit. Sunny most days.
63°
85°
weather_sun
July, Moderate crowds, average high temperature 85 degrees Fahrenheit, average low temperature 67 degrees Fahrenheit. Sunny most days.
67°
84°
weather_sun
August, High crowds, average high temperature 84 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
78°
weather_sun
September, Moderate crowds, average high temperature 78 degrees Fahrenheit, average low temperature 60 degrees Fahrenheit. Sunny most days.
60°
67°
weather_sun
October, High crowds, average high temperature 67 degrees Fahrenheit, average low temperature 49 degrees Fahrenheit. Sunny most days.
49°
54°
weather_partly_sunny
November, Moderate crowds, average high temperature 54 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Partly sunny.
37°
46°
weather_cloudy
December, Low crowds, average high temperature 46 degrees Fahrenheit, average low temperature 32 degrees Fahrenheit. Cloudy most days.
32°
40°
ac_unit
January, Low crowds, average high temperature 40 degrees Fahrenheit, average low temperature 26 degrees Fahrenheit. Snow likely.
26°
45°
weather_cloudy
February, Low crowds, average high temperature 45 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Cloudy most days.
29°
55°
weather_cloudy
March, Low crowds, average high temperature 55 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Cloudy most days.
37°
65°
weather_sun
April, High crowds, average high temperature 65 degrees Fahrenheit, average low temperature 46 degrees Fahrenheit. Sunny most days.
46°
Monthly weather averages (˚F)
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Top landmarks in Winchester

Bluegrass Heritage Museum

The centre of Winchester is home to cultural attractions like Bluegrass Heritage Museum, so you might want to stop by during your stay. If you want to experience more of the culture Winchester has to offer, head to Clark Regional Medical Center, Lykins Park, and Southwind Golf Course.

See properties in Bluegrass Heritage Museum
Bluegrass Heritage Museum

Learn more about Winchester

Winchester is well-known for its attractions such as Bluegrass Heritage Museum and Lykins Park. Visitors to this welcoming city speak highly of the restaurants whereas sights include Southwind Golf Course and Cassell Creek Golf Course.

See all hotels in Winchester
Canoeing down the Kentucky river 🚣
Photo by Hyelsinta
Open Photo by Hyelsinta
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?
Holiday Inn Express Lexington East - Winchester by IHG, Hampton Inn Winchester and Value Stays by OYO I-64 are all properties that our guests really like.
Where can I find free parking with my stay in Winchester?
Park your car for free at these properties: Baymont by Wyndham Winchester, Comfort Inn and Holiday Inn Express Lexington East - Winchester, an IHG Hotel. There are 5 choices you may want to check out on our site.
Can I book refundable hotels in Winchester?
If you want the flexibility to change your plans to Winchester, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the “fully refundable” filter to narrow the results down.
Where can I stay with my pet in Winchester?
Your furry friend can stay with you at these pet-friendly hotels: Baymont by Wyndham Winchester, Best Western Winchester Hotel and Hampton Inn Winchester. There are 5 alternatives to choose from on our site.
Which Winchester hotels do travelers like for their central location?
Travelers like these properties for their good location: Hampton Inn Winchester and Holiday Inn Express Lexington East - Winchester, an IHG Hotel.
Where should I stay in Winchester if I'm looking for a cheap accommodation?
A few inexpensive options worth considering are Hampton Inn Winchester, Best Western Winchester Hotel and Baymont by Wyndham Winchester.
Where can I stay in Winchester if I want a vacation home instead of a traditional hotel?
Browse 7 vacation homes on our site.
Where can I stay if I'm visiting Winchester with my family?
Your kids are welcome at Hampton Inn Winchester.
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 38°F. April and July 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.

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.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

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