Hotels in Winchester

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Check prices for these dates

Tonight
Apr 14 - Apr 15
Tomorrow
Apr 15 - Apr 16
This weekend
Apr 17 - Apr 19
Next weekend
Apr 24 - Apr 26

Where to stay in Winchester?

Free daily full breakfast
Best Western Winchester Hotel
Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,001 reviews)
Enjoy a quiet respite at this Winchester hotel, featuring a seasonal outdoor pool and complimentary full breakfast. With free parking and helpful staff praised by travelers, you'll find comfort minutes from Wiseman Park and Community Park.
The price is $90
$99 total
includes taxes & fees
Apr 16 - Apr 17
Best Western Winchester Hotel
Indoor pool
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (786 reviews)
Retreat to this quiet Winchester hotel with its peaceful atmosphere and clean rooms. Start your day with a free breakfast, then enjoy a refreshing swim in the indoor pool. The fitness center, free WiFi, and parking enhance your stay near The Holler and Lykins Park.
The price is $76
$83 total
includes taxes & fees
Apr 21 - Apr 22
Baymont by Wyndham Winchester
Suite, 1 King Bed, Hot Tub | Free WiFi, bed sheets
Value Stay
Value Stay
2.0 star property
Winchester
7.8 out of 10, Good, (135 reviews)
Situated close to Community Park and Wiseman Park, this motel offers convenient amenities including free WiFi and complimentary parking. The 24-hour front desk ensures assistance is always available during your Winchester visit.
The price is $48
$53 total
includes taxes & fees
Apr 16 - Apr 17
Value Stay
Exterior
Red Roof Inn Winchester - Lexington East
Red Roof Inn Winchester - Lexington East
2.0 star property
Winchester
6.4 out of 10, (593 reviews)
This roadside hotel offers stress-free travel with complimentary amenities and round-the-clock front desk assistance. Located near The Holler and Lykins Park, you'll find easy access to local attractions just 32 minutes from Blue Grass Airport.
The price is $67
$74 total
includes taxes & fees
Apr 18 - Apr 19
Red Roof Inn Winchester - Lexington East
Indoor pool
Comfort Inn Winchester
Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (360 reviews)
Discover a tranquil retreat with an indoor pool for morning swims and full fitness center. Just minutes from Community Park and Wiseman Park, this Winchester hotel offers free WiFi and complimentary parking for easy exploration.
The price is $69
$76 total
includes taxes & fees
May 15 - May 16
Comfort Inn Winchester
In-room safe, desk, laptop workspace, blackout drapes
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, (557 reviews)
Set near Wiseman Park, this hotel offers an indoor pool for year-round swimming and a 24-hour fitness center. Free parking makes exploring easy, while the helpful staff ensures a comfortable stay with complimentary breakfast to start your day.
The price is $134
$148 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn Express Lexington East - Winchester by IHG
Lobby
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (461 reviews)
Discover a tranquil haven where safety and quiet comfort await. Located near The Holler and Lykins Park, this Winchester hotel offers a refreshing seasonal outdoor pool and convenient fitness center, plus free breakfast, WiFi and parking.
The price is $125
$138 total
includes taxes & fees
May 10 - May 11
Hampton Inn Winchester
Cabin, 2 Bedrooms, Kitchen | Living area | 32-inch flat-screen TV with cable channels, TV
Natural Bridge State Resort Park
Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,848 reviews)
The price is $116
$128 total
includes taxes & fees
May 3 - May 4
Natural Bridge State Resort Park
Exterior
Black Bear Lodge Motel
Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (646 reviews)
Tucked against Natural Bridge State Park, this cozy lodge invites outdoor adventures. Clean rooms with satellite TV await after exploring nearby Red River Gorge. Enjoy the picnic area and free parking while helpful staff ensure a memorable mountain getaway.
The price is $88
$97 total
includes taxes & fees
Apr 16 - Apr 17
Black Bear Lodge Motel
Indoor pool
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (734 reviews)
Start your day with a complimentary breakfast at this quiet Mount Sterling retreat. The indoor pool invites morning dips while the hot tub soothes evening tensions. Clean rooms and attentive staff create a peaceful atmosphere near Old Silo Golf Course.
The price is $88
$97 total
includes taxes & fees
Apr 26 - Apr 27
Comfort Inn & Suites Mount Sterling
Lobby sitting area
Ramada Limited Mount Sterling
Ramada Limited Mount Sterling
2.0 star property
Mount Sterling
7.0 out of 10, Good, (805 reviews)
Wake up to free breakfast at this peaceful Mount Sterling retreat near the local library. The helpful staff, indoor pool, and 24-hour fitness center create a welcoming atmosphere, while clean rooms with free WiFi ensure a comfortable business trip.
The price is $69
$76 total
includes taxes & fees
Apr 29 - Apr 30
Ramada Limited Mount Sterling
Exterior
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, (602 reviews)
Just minutes from Old Silo Golf Course, this welcoming hotel offers an indoor pool and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while the attentive staff ensures a comfortable stay near Mount Sterling Library.
The price is $122
$134 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn Express & Suites Mt Sterling North by IHG
Exterior
Clarion Pointe Richmond North near University
Clarion Pointe Richmond North near University
2.5 star property
Richmond
8.2 out of 10, Very Good, (953 reviews)
Wake up to free continental breakfast on weekdays before exploring nearby E.C. Million Park. This hotel offers clean rooms with complimentary WiFi and parking. University-adjacent location earns praise from guests for its peaceful atmosphere and helpful staff.
The price is $81
$89 total
includes taxes & fees
May 10 - May 11
Clarion Pointe Richmond North near University
Standard Room, 2 Queen Beds | Desk, blackout drapes, iron/ironing board, free WiFi
Super 8 by Wyndham Richmond
Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.6 out of 10, Good, (1,000 reviews)
This quiet Richmond motel offers free WiFi and on-the-go breakfast, making mornings easier. You'll be near E.C. Million Park and Richmond Area Arts Center. Guests consistently praise the helpful staff and clean, restful rooms.
The price is $55
$61 total
includes taxes & fees
Apr 16 - Apr 17
Super 8 by Wyndham Richmond
Indoor pool
Baymont by Wyndham Richmond KY
Baymont by Wyndham Richmond KY
2.5 star property
Richmond
7.0 out of 10, Good, (1,011 reviews)
Set near Richmond Centre Mall and Cinemark, this hotel offers an indoor pool and 24-hour fitness center. Clean rooms provide a relaxing retreat after enjoying the free breakfast and parking. Travelers consistently praise the friendly, accommodating staff.
The price is $71
$78 total
includes taxes & fees
Apr 20 - Apr 21
Baymont by Wyndham Richmond KY
Exterior
TownePlace Suites by Marriott Richmond
TownePlace Suites by Marriott Richmond
3.0 star property
Richmond
9.4 out of 10, Exceptional, (278 reviews)
Wake up to free breakfast and energize in the 24-hour fitness center at this welcoming hotel. Conveniently located near Richmond Centre Mall and Cinemark, you'll enjoy free parking and WiFi while exploring local attractions.
The price is $144
$159 total
includes taxes & fees
Apr 19 - Apr 20
TownePlace Suites by Marriott Richmond
Suite, 1 King Bed with Sofa bed, Non Smoking, Hot Tub | Desk, laptop workspace, iron/ironing board, free cribs/infant beds
Comfort Suites Richmond
Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (736 reviews)
Discover a serene retreat with an indoor pool and fitness center just minutes from Richmond Centre Mall. Free breakfast, WiFi, and parking add exceptional value, while the helpful staff ensures your comfort throughout your stay.
The price is $90
$99 total
includes taxes & fees
Apr 19 - Apr 20
Comfort Suites Richmond
Interior entrance
Quality Inn Richmond
Quality Inn Richmond
2.5 star property
Richmond
9.0 out of 10, Wonderful, (1,018 reviews)
Splash into the seasonal outdoor pool at this Richmond hotel, where clean rooms and attentive staff await. Near Richmond Centre Mall and Cinemark, with 24-hour fitness center access. Free breakfast, WiFi, and parking enhance your stay.
The price is $99
$109 total
includes taxes & fees
Apr 19 - Apr 20
Quality Inn Richmond
Terrace/patio
Home2 Suites By Hilton Richmond, Ky
Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (210 reviews)
The price is $106
$117 total
includes taxes & fees
Apr 21 - Apr 22
Home2 Suites By Hilton Richmond, Ky
Indoor pool
Hampton Inn Richmond
Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,011 reviews)
Wake up to a complimentary breakfast at this quiet Richmond hotel before exploring nearby attractions. The indoor pool offers year-round swimming, while convenient highway access and free parking make travel stress-free.
The price is $106
$117 total
includes taxes & fees
May 10 - May 11
Hampton Inn Richmond
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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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, (1001)
The price is $90
$99 total
includes taxes & fees
Apr 16 - Apr 17
Best Western Winchester Hotel
View all properties

You may also like pet-friendly hotels in 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, (135)
The price is $48
$53 total
includes taxes & fees
Apr 16 - Apr 17
Value Stay
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 April
Currently viewing crowd sizes and weather for April.
Typical weather for Winchester
April
High 18°C / low 8°C. Sunny most days.
View properties in April
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°
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
29°
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August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
19°
26°
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September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
19°
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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°
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December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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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°
weather_cloudy
February, no crowd data, average high temperature 7 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
-2°
13°
weather_cloudy
March, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
3°
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.
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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.

See all hotels in Winchester
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

Hyatt Regency Lexington

Hyatt Regency Lexington

10/10 Excellent
"Perfect location, very clean "
Kristen 2-night trip
Posted 1 hour 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.