Photo by Nawa Aseen

Hotels in Winchester

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Check prices for these dates

Tonight
Jan 13 - Jan 14
Tomorrow
Jan 14 - Jan 15
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Where to stay in Winchester?

Free daily full breakfast
Best Western Winchester Hotel
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,000 reviews)
The price is $72
$80 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Winchester Hotel
In-room safe, desk, laptop workspace, blackout drapes
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (532 reviews)
The price is $97
$107 total
includes taxes & fees
Jan 20 - Jan 21
Holiday Inn Express Lexington East - Winchester by IHG
Lobby
Hampton Inn Winchester
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (455 reviews)
The price is $126
$139 total
includes taxes & fees
Jan 19 - Jan 20
Hampton Inn Winchester
Indoor pool
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (773 reviews)
The price is $76
$83 total
includes taxes & fees
Jan 14 - Jan 15
Baymont by Wyndham Winchester
Exterior
Red Roof Inn Winchester - Lexington East
Red Roof Inn Winchester - Lexington East
Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (588 reviews)
The price is $62
$69 total
includes taxes & fees
Jan 18 - Jan 19
Red Roof Inn Winchester - Lexington East
Indoor pool
Comfort Inn Winchester
Comfort Inn Winchester
Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (353 reviews)
The price is $72
$80 total
includes taxes & fees
Feb 2 - Feb 3
Comfort Inn Winchester
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets
Value Stay
Value Stay
Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (127 reviews)
The price is $67
$74 total
includes taxes & fees
Jan 14 - Jan 15
Value Stay
Indoor pool, sun loungers
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,205 reviews)
The price is $90
$105 total
includes taxes & fees
Jan 15 - Jan 16
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lobby
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,008 reviews)
The price is $58
$67 total
includes taxes & fees
Jan 15 - Jan 16
Days Inn Lexington SE/Hamburg
Lobby
Comfort Inn Lexington I-75
Comfort Inn Lexington I-75
Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (734 reviews)
The price is $71
$83 total
includes taxes & fees
Jan 14 - Jan 15
Comfort Inn Lexington I-75
Reception
Hotel LEX, Trademark Collection by Wyndham
Hotel LEX, Trademark Collection by Wyndham
Hotel LEX, Trademark Collection by Wyndham
3.0 star property
Lexington
8.4 out of 10, Very Good, (576 reviews)
The price is $71
$82 total
includes taxes & fees
Jan 23 - Jan 24
Hotel LEX, Trademark Collection by Wyndham
Exterior
Holiday Inn Lexington - Hamburg by IHG
Holiday Inn Lexington - Hamburg by IHG
Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,003 reviews)
The price is $88
$102 total
includes taxes & fees
Jan 23 - Jan 24
Holiday Inn Lexington - Hamburg by IHG
Lobby
Hyatt Place Lexington
Hyatt Place Lexington
Hyatt Place Lexington
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,005 reviews)
The price is $101
$117 total
includes taxes & fees
Jan 14 - Jan 15
Hyatt Place Lexington
Exterior
avid hotel Lexington - Hamburg Area by IHG
avid hotel Lexington - Hamburg Area by IHG
avid hotel Lexington - Hamburg Area by IHG
2.5 star property
Lexington
9.2 out of 10, Wonderful, (886 reviews)
The price is $78
$91 total
includes taxes & fees
Jan 18 - Jan 19
avid hotel Lexington - Hamburg Area by IHG
Terrace/patio
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,001 reviews)
The price is $98
$113 total
includes taxes & fees
Jan 17 - Jan 18
Home2 Suites by Hilton Lexington Hamburg
Breakfast and dinner served, American cuisine
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (852 reviews)
The price is $84
$97 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Lexington Hamburg
Outdoor pool, pool umbrellas, sun loungers
Homewood Suites Lexington-Hamburg
Homewood Suites Lexington-Hamburg
Homewood Suites Lexington-Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (665 reviews)
The price is $100
$115 total
includes taxes & fees
Jan 28 - Jan 29
Homewood Suites Lexington-Hamburg
Exterior
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHG
Holiday Inn Express & Suites Mt Sterling North by IHG
2.5 star property
Mount Sterling
8.8 out of 10, Excellent, (578 reviews)
The price is $89
$98 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Express & Suites Mt Sterling North by IHG
Lobby lounge
Sleep Inn Lexington
Sleep Inn Lexington
Sleep Inn Lexington
2.5 star property
Liberty Area
7.8 out of 10, Good, (810 reviews)
The price is $69
$80 total
includes taxes & fees
Jan 20 - Jan 21
Sleep Inn Lexington
Indoor pool
Hampton Inn I-75 Lexington/Hamburg Area
Hampton Inn I-75 Lexington/Hamburg Area
Hampton Inn I-75 Lexington/Hamburg Area
2.5 star property
Lexington
8.6 out of 10, Excellent, (975 reviews)
The price is $81
$94 total
includes taxes & fees
Jan 30 - Jan 31
Hampton Inn I-75 Lexington/Hamburg Area
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.
View all properties

Check out hotels with a pool in Winchester

Free daily full breakfast
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1000)
The price is $72
$80 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Winchester Hotel
View all properties

You may also like pet-friendly hotels in Winchester

Free daily full breakfast
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1000)
The price is $72
$80 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Winchester Hotel
View all properties

You can also stay at family-friendly hotels in Winchester

Free daily full breakfast
Best Western Winchester Hotel

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1000)
The price is $72
$80 total
includes taxes & fees
Jan 18 - Jan 19
Best Western Winchester Hotel
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.
View all properties

When is the best time to visit Winchester?

Our prices for hotels in Winchester are cheapest in December
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
View properties in January
Currently viewing crowd sizes and weather for January.
Typical weather for Winchester
January
High 4°C / low -3°C. Snow likely.
View properties in January
4°
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
7°
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February, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
13°
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March, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
3°
18°
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April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
23°
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May, no crowd data, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
13°
28°
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June, no crowd data, average high temperature 28 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
29°
weather_sun
July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
weather_sun
August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
26°
weather_sun
September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
19°
weather_sun
October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
9°
12°
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
8°
weather_cloudy
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
0°
Monthly weather averages (˚C)

Top landmarks in Winchester

Winchester Traveling Trail

Stroll through a mile of Kentucky bluegrass on this peaceful meadow trail with strategically placed benches for breaks. Leashed dogs are welcome, making it a favorite spot for locals seeking a quick nature escape.
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Bluegrass Heritage Museum

Step back in time at this Romanesque Revival building housing three floors of Bluegrass region history. Don't miss the preserved operating room that offers a fascinating glimpse into early medical practices.
See properties

Learn more about Winchester

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

See all hotels in Winchester
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

Check out reviews of Winchester hotels guests love

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Clean room. Friendly and helpful staff. Smooth check in and check out experience. "
Ethan 1-night trip
Posted 1 day ago
Hyatt Regency Lexington

Frequently asked questions

What hotels do travelers like in Winchester?
Holiday Inn Express Lexington East - Winchester by IHG, Hampton Inn Winchester and Best Western Winchester Hotel are all properties that our guests really like.
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 in Winchester if I want a vacation home instead of a traditional hotel?
Browse 6 vacation homes on our site.
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.