Hotels in Winchester

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Where to stay in Winchester?

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (157 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 $65
$72 total
includes taxes & fees
Jun 19 - Jun 20
Value Stay

Best Western Winchester Hotel

Best Western Winchester Hotel
2.5 star property
Winchester
8.4 out of 10, Very Good, (1,002 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
Jun 23 - Jun 24
Best Western Winchester Hotel

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (809 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 $79
$87 total
includes taxes & fees
Jun 25 - Jun 26
Baymont by Wyndham Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (471 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 $129
$142 total
includes taxes & fees
Jul 6 - Jul 7
Hampton Inn Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (367 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 $73
$81 total
includes taxes & fees
Jul 19 - Jul 20
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, (570 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 $110
$121 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express Lexington East - Winchester by IHG

Black Bear Lodge Motel

Black Bear Lodge Motel
2.5 star property
Slade
8.0 out of 10, Very Good, (677 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
Jun 24 - Jun 25
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, (758 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 $93
$103 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Inn & Suites Mount Sterling

Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (229 reviews)
Located a short drive from Rupp Arena and University of Kentucky, this Lexington hotel offers complimentary daily buffet breakfast, WiFi, and parking. Stay active in the fitness center while Kroger Field and Blue Grass Airport remain easily accessible.
The price is $84
$98 total
includes taxes & fees
Jun 29 - Jun 30
Tru By Hilton Lexington Hamburg

Natural Bridge State Resort Park

Natural Bridge State Resort Park
3.5 star property
Slade
8.6 out of 10, Excellent, (1,930 reviews)
The price is $136
$150 total
includes taxes & fees
Jul 19 - Jul 20
Natural Bridge State Resort Park

Super 8 by Wyndham Richmond

Super 8 by Wyndham Richmond
2.0 star property
Richmond
7.8 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
Jun 21 - Jun 22
Super 8 by Wyndham Richmond

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,018 reviews)
Find peaceful rest at this motel with clean rooms and helpful staff. Just minutes from Kroger Field and Rupp Arena, guests enjoy free WiFi and on-the-go breakfast daily. Nearby attractions and University of Kentucky make this a convenient hub.
The price is $41
$48 total
includes taxes & fees
Jun 30 - Jul 1
Days Inn Lexington SE/Hamburg

Hampton Inn Richmond

Hampton Inn Richmond
2.5 star property
Richmond
9.2 out of 10, Wonderful, (1,012 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 $107
$118 total
includes taxes & fees
Jul 2 - Jul 3
Hampton 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, (243 reviews)
The price is $130
$144 total
includes taxes & fees
Jun 28 - Jun 29
Home2 Suites By Hilton Richmond, Ky

Country Inn & Suites by Radisson, Georgetown, KY

Country Inn & Suites by Radisson, Georgetown, KY
3.0 star property
Georgetown
8.8 out of 10, Excellent, (1,001 reviews)
The price is $73
$80 total
includes taxes & fees
Jul 19 - Jul 20
Country Inn & Suites by Radisson, Georgetown, KY

Hotel Thoroughbred

Hotel Thoroughbred
2.0 star property
Paris
10.0 out of 10, Exceptional, (13 reviews)
The price is $164
$181 total
includes taxes & fees
Jun 19 - Jun 20
Hotel Thoroughbred

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, (1,162 reviews)
Serene retreat with an indoor pool and fitness center just 15 minutes from Rupp Arena and University of Kentucky. Near interstate access and restaurants, this hotel offers free breakfast, WiFi, and parking. Guests praise the helpful staff and quiet atmosphere.
The price is $90
$105 total
includes taxes & fees
Jun 21 - Jun 22
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Microtel Inn by Wyndham Georgetown

Microtel Inn by Wyndham Georgetown
2.0 star property
Georgetown
7.8 out of 10, Good, (999 reviews)
Enjoy quiet rooms and fuel up with complimentary continental breakfast before exploring Georgetown. This hotel offers free WiFi and parking, with Kentucky Horse Park just 10 minutes away. Hiking trails invite outdoor adventure while helpful staff ensure a comfortable business stay.
The price is $67
$73 total
includes taxes & fees
Jun 21 - Jun 22
Microtel Inn by Wyndham Georgetown

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,000 reviews)
The price is $98
$114 total
includes taxes & fees
Jul 4 - Jul 5
Holiday Inn Lexington - Hamburg by IHG

Asbury Inn & Suites

Asbury Inn & Suites
3.0 star property
Wilmore
9.6 out of 10, Exceptional, (509 reviews)
Wake up to a complimentary breakfast at this Wilmore hotel offering 24-hour fitness facilities and free parking. Near B. L. Fisher Library and Wilmore Mini Park, guests appreciate the friendly staff and convenient amenities for a smooth Kentucky visit.
The price is $129
$142 total
includes taxes & fees
Jun 22 - Jun 23
Asbury Inn & Suites
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 January
Price trends for hotels in Winchester
Pricing is based on two traveler single night rates
View properties in June
Currently viewing crowd sizes and weather for June.
Typical weather for Winchester
June
High 28°C / low 17°C. Sunny most days.
View properties in June
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.
12°
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November, no crowd data, average high temperature 12 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
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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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January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-3°
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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.
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°
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.

An aerial view of a historic town with a prominent clock tower, narrow streets lined with historic buildings, and a mix of commercial and residential areas.

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 5 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.