Hotels in Winchester

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Where to stay in Winchester?

Value Stay
Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (132 reviews)
  • cleanliness
    Near downtown Winchester with free parking and WiFi for a smooth stay.
The price is $59
$65 total
includes taxes & fees
Mar 23 - Mar 24
Value Stay
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (778 reviews)
  • cleanliness
    Peaceful Winchester stay with clean rooms and indoor pool for year-round swimming.
The price is $76
$83 total
includes taxes & fees
Mar 23 - Mar 24
Baymont by Wyndham Winchester
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Stay at a peaceful spot with easy interstate access and tranquil rooms to rest in.
The price is $85
$94 total
includes taxes & fees
Mar 26 - Mar 27
Best Western Winchester Hotel
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (458 reviews)
  • cleanliness
    Unwind in a peaceful Winchester retreat with seasonal outdoor pool and fitness center.
The price is $114
$126 total
includes taxes & fees
Mar 29 - Mar 30
Hampton Inn Winchester
Comfort Inn Winchester
Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (358 reviews)
  • cleanliness
    Peaceful Winchester stay with indoor swimming and fitness near Community Park.
The price is $69
$76 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn Winchester
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.2 out of 10, Wonderful, (552 reviews)
  • cleanliness
    Experience Winchester with a complimentary breakfast after your morning swim at the pool.
The price is $113
$125 total
includes taxes & fees
Mar 29 - Mar 30
Holiday Inn Express Lexington East - Winchester by IHG
Red Roof Inn Winchester - Lexington East
Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (592 reviews)
  • cleanliness
    Stay connected in Winchester with free Wi-Fi, parking, and 24-hour service.
The price is $62
$69 total
includes taxes & fees
Mar 25 - Mar 26
Red Roof Inn Winchester - Lexington East
Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,826 reviews)
The price is $111
$122 total
includes taxes & fees
Apr 15 - Apr 16
Natural Bridge State Resort Park
Black Bear Lodge Motel
Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (643 reviews)
  • cleanliness
    Modern lodge with rustic charm near Natural Bridge State Park and Red River Gorge.
The price is $88
$97 total
includes taxes & fees
Mar 23 - Mar 24
Black Bear Lodge Motel
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (727 reviews)
  • cleanliness
    Serene Mount Sterling hotel with indoor pool for morning swims and relaxing hot tub.
The price is $78
$86 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn & Suites Mount Sterling
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, (593 reviews)
  • cleanliness
    Unwind in Mount Sterling with convenient amenities and friendly service.
The price is $95
$105 total
includes taxes & fees
Mar 29 - Mar 30
Holiday Inn Express & Suites Mt Sterling North by IHG
Best Western Paris Inn
Best Western Paris Inn
2.5 star property
Paris
7.8 out of 10, Good, (351 reviews)
The price is $102
$112 total
includes taxes & fees
Mar 23 - Mar 24
Best Western Paris Inn
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near University
2.5 star property
Richmond
8.2 out of 10, Very Good, (928 reviews)
  • cleanliness
    Tranquil, convenient Richmond stay with university proximity and traveler perks.
The price is $74
$81 total
includes taxes & fees
Apr 12 - Apr 13
Clarion Pointe Richmond North near University
Super 8 by Wyndham Richmond
Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.6 out of 10, Good, (1,002 reviews)
  • cleanliness
    Peaceful Richmond motel near area attractions with free parking and breakfast.
The price is $54
$60 total
includes taxes & fees
Mar 23 - Mar 24
Super 8 by Wyndham Richmond
Baymont by Wyndham Richmond KY
Baymont by Wyndham Richmond KY
2.5 star property
Richmond
7.0 out of 10, Good, (1,004 reviews)
  • cleanliness
    Enjoy modern comfort with a pool, fitness center, and helpful staff in Richmond.
The price is $68
$75 total
includes taxes & fees
Mar 29 - Mar 30
Baymont by Wyndham Richmond KY
TownePlace Suites by Marriott Richmond
TownePlace Suites by Marriott Richmond
3.0 star property
Richmond
9.4 out of 10, Exceptional, (278 reviews)
  • cleanliness
    Stylish Richmond hotel with in-room kitchens, daily buffet breakfast, and fitness.
The price is $144
$159 total
includes taxes & fees
Mar 29 - Mar 30
TownePlace Suites by Marriott Richmond
Quality Inn Richmond
Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Downtown Richmond hotel with seasonal pool near shopping and cinema attractions.
The price is $99
$109 total
includes taxes & fees
Mar 23 - Mar 24
Quality Inn Richmond
Home2 Suites By Hilton Richmond, Ky
Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (181 reviews)
The price is $98
$108 total
includes taxes & fees
Apr 2 - Apr 3
Home2 Suites By Hilton Richmond, Ky
Hampton Inn Richmond
Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Modern hotel near Richmond Centre with pool and fitness center for active travelers.
The price is $98
$108 total
includes taxes & fees
Apr 5 - Apr 6
Hampton Inn Richmond
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, (1,158 reviews)
  • cleanliness
    Peaceful stay near Rupp Arena with convenient access to local dining options.
The price is $93
$108 total
includes taxes & fees
Mar 23 - Mar 24
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
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.

Check out pet-friendly hotels in Winchester

You may also like hotels with pools 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.

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 March
Currently viewing crowd sizes and weather for March.
Typical weather for Winchester
March
High 13°C / low 3°C. Cloudy most days.
View properties in March
13°
weather_cloudy
March, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
18°
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April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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.
12°
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
weather_cloudy
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
weather_cloudy
February, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
Monthly weather averages (˚C)

Top landmarks in Winchester

Learn more about Winchester

Beneath the shadow of the Bluegrass Heritage Museum, Main Street reveals a parade of antique shops where yesterday's treasures await discovery. The Winchester Opera House stands as a cultural cornerstone in this small Kentucky town with big character. Escape to Daniel Boone National Forest, where hiking trails wind through Appalachian wilderness that would make the legendary frontiersman feel right at home. College Park offers a peaceful retreat when urban exploration tires the feet. Local eateries serve up authentic flavors that chain restaurants can't replicate. For golf enthusiasts, Southwind Golf Course presents challenging fairways with scenic vistas. The Clark County Courthouse anchors the historic downtown, its architecture telling stories of bygone eras without saying a word.

MAY 9, 2023 - WINCHESTER, KENTUCKY - aerial view of historic small town of Winchester with Town Clocktower and historic storefronts and buildings

Check out reviews of Winchester hotels guests love

Frequently asked questions

What hotels do travelers like in Winchester?
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.