Hotels in Winchester

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Where to stay in Winchester?

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 $85
$94 total
includes taxes & fees
Jul 5 - Jul 6
Best Western Winchester Hotel

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (158 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 $59
$65 total
includes taxes & fees
Aug 1 - Aug 2
Value Stay

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (817 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
Jul 26 - Jul 27
Baymont by Wyndham Winchester

Comfort Inn Winchester

Comfort Inn Winchester
2.5 star property
Winchester
7.0 out of 10, Good, (370 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
$77 total
includes taxes & fees
Jul 26 - Jul 27
Comfort Inn Winchester

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (472 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 $133
$146 total
includes taxes & fees
Jul 26 - Jul 27
Hampton 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, (575 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 $118
$130 total
includes taxes & fees
Jul 30 - Jul 31
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, (686 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
Jul 5 - Jul 6
Black Bear Lodge Motel

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
Jul 2 - Jul 3
Super 8 by Wyndham Richmond

Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (236 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 $89
$103 total
includes taxes & fees
Jul 15 - Jul 16
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, (1,943 reviews)
The price is $141
$155 total
includes taxes & fees
Jul 12 - Jul 13
Natural Bridge State Resort Park

Comfort Inn & Suites Mount Sterling

Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (763 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 $91
$100 total
includes taxes & fees
Jul 5 - Jul 6
Comfort Inn & Suites Mount Sterling

Home2 Suites By Hilton Richmond, Ky

Home2 Suites By Hilton Richmond, Ky
3.0 star property
Richmond
9.6 out of 10, Exceptional, (252 reviews)
The price is $130
$144 total
includes taxes & fees
Jul 8 - Jul 9
Home2 Suites By Hilton Richmond, Ky

Comfort Suites Richmond

Comfort Suites Richmond
2.5 star property
Richmond
7.4 out of 10, Good, (762 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 $49
$54 total
includes taxes & fees
Jul 28 - Jul 29
Comfort Suites Richmond

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,003 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 $48
$56 total
includes taxes & fees
Jul 12 - Jul 13
Days Inn Lexington SE/Hamburg

Asbury Inn & Suites

Asbury Inn & Suites
3.0 star property
Wilmore
9.6 out of 10, Exceptional, (515 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
Jul 2 - Jul 3
Asbury Inn & Suites

Hampton Inn Lexington South-Keeneland/Airport

Hampton Inn Lexington South-Keeneland/Airport
2.5 star property
Beaumont Residential
8.2 out of 10, Very Good, (626 reviews)
Energize your Lexington stay at this ideally located hotel near Kroger Field and Rupp Arena. Start each morning with complimentary buffet breakfast before exploring nearby attractions. The helpful staff, fitness center, and free WiFi create a comfortable base for business or leisure trips.
The price is $77
$90 total
includes taxes & fees
Jul 4 - Jul 5
Hampton Inn Lexington South-Keeneland/Airport

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, (1,010 reviews)
The price is $83
$91 total
includes taxes & fees
Jul 15 - Jul 16
Country Inn & Suites by Radisson, Georgetown, KY

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, (1,169 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 $82
$95 total
includes taxes & fees
Jul 5 - Jul 6
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Hotel Thoroughbred

Hotel Thoroughbred
2.0 star property
Paris
10.0 out of 10, Exceptional, (17 reviews)
The price is $164
$181 total
includes taxes & fees
Jul 2 - Jul 3
Hotel Thoroughbred

Baymont by Wyndham Georgetown/Lexington North

Baymont by Wyndham Georgetown/Lexington North
2.5 star property
Georgetown
8.0 out of 10, Very Good, (1,003 reviews)
Wake up to a free breakfast at this quiet Georgetown hotel near Kentucky Horse Park. Take a refreshing swim in the indoor pool, squeeze in a workout at the fitness center, or explore nearby restaurants. Clean rooms and helpful staff create a peaceful, convenient stay.
The price is $68
$75 total
includes taxes & fees
Jul 5 - Jul 6
Baymont by Wyndham Georgetown/Lexington North
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 July
Currently viewing crowd sizes and weather for July.
Typical weather for Winchester
July
High 29°C / low 19°C. Sunny most days.
View properties in July
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°
weather_cloudy
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°
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°
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 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.