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, (1,000 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 $95
$105 total
includes taxes & fees
Jun 11 - Jun 12
Best Western Winchester Hotel

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (808 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 $85
$93 total
includes taxes & fees
Jul 1 - Jul 2
Baymont by Wyndham Winchester

Value Stay

Value Stay
2.0 star property
Winchester
7.6 out of 10, Good, (156 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 11 - Jun 12
Value Stay

Hampton Inn Winchester

Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (468 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 $130
$144 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, (366 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 $75
$83 total
includes taxes & fees
Jul 1 - Jul 2
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, (569 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 $122
$134 total
includes taxes & fees
Jul 9 - Jul 10
Holiday Inn Express Lexington East - Winchester by IHG

Days Inn Lexington SE/Hamburg

Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,009 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 $43
$50 total
includes taxes & fees
Jun 30 - Jul 1
Days Inn Lexington SE/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, (1,167 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 14 - Jun 15
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

Comfort Inn Lexington I-75

Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (777 reviews)
This welcoming Lexington hotel offers a peaceful stay with an indoor pool and fitness center. Just 15 minutes from Rupp Arena, you'll appreciate the free breakfast, WiFi, and parking. Guests praise the helpful staff and clean, quiet rooms near local attractions.
The price is $71
$83 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Inn Lexington I-75

Hotel LEX, Trademark Collection by Wyndham

Hotel LEX, Trademark Collection by Wyndham
3.0 star property
Lexington
8.0 out of 10, Very Good, (736 reviews)
Immerse yourself in Lexington's charm at this welcoming hotel with an indoor pool and on-site restaurant. Just a 15-minute drive from Rupp Arena and University of Kentucky, with convenient access to Kroger Field and local attractions.
The price is $77
$90 total
includes taxes & fees
Jun 16 - Jun 17
Hotel LEX, Trademark Collection by Wyndham

Hyatt Place Lexington

Hyatt Place Lexington
3.0 star property
Lexington
8.6 out of 10, Excellent, (1,001 reviews)
Stay minutes from top attractions at this Lexington hotel with an indoor pool and 24-hour fitness center. Grab a bite at the café or unwind at the bar after a busy day. Free breakfast, WiFi, and parking add value to rooms with sofa beds and fridges.
The price is $107
$124 total
includes taxes & fees
Jun 13 - Jun 14
Hyatt Place Lexington

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,011 reviews)
The price is $98
$114 total
includes taxes & fees
Jul 3 - Jul 4
Holiday Inn Lexington - Hamburg by IHG

Tru By Hilton Lexington Hamburg

Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (225 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 $85
$99 total
includes taxes & fees
Jun 29 - Jun 30
Tru By Hilton Lexington Hamburg

Hilton Garden Inn Lexington Hamburg

Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (895 reviews)
The price is $85
$99 total
includes taxes & fees
Jun 21 - Jun 22
Hilton Garden Inn Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg

Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.4 out of 10, Exceptional, (1,015 reviews)
Bright, modern suites with kitchen essentials await at this Lexington hotel near Kroger Field. Enjoy complimentary breakfast, WiFi, and parking, plus an indoor pool and fitness center. Just 15 minutes from Rupp Arena with attentive staff to enhance your stay.
The price is $114
$132 total
includes taxes & fees
Jun 14 - Jun 15
Home2 Suites by Hilton Lexington Hamburg

Courtyard Lexington South/Hamburg Place

Courtyard Lexington South/Hamburg Place
3.0 star property
Lexington
8.6 out of 10, Excellent, (383 reviews)
This Lexington hotel offers easy access to Kroger Field and Red Mile Racetrack. Enjoy American cuisine at The Bistro restaurant, unwind at the bar, or maintain your routine in the fitness center. Free WiFi and parking enhance your stay with attentive staff.
The price is $128
$149 total
includes taxes & fees
Jun 14 - Jun 15
Courtyard Lexington South/Hamburg Place

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, (613 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 $139
$153 total
includes taxes & fees
Jul 5 - Jul 6
Holiday Inn Express & Suites Mt Sterling North 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, (969 reviews)
Just a 15-minute drive from Rupp Arena and University of Kentucky, this modern hotel offers complimentary WiFi, parking, and daily breakfast. Guests appreciate the helpful staff, clean rooms, and convenient access to nearby shopping.
The price is $93
$108 total
includes taxes & fees
Jun 14 - Jun 15
avid hotel Lexington - Hamburg Area by IHG

Sleep Inn Lexington

Sleep Inn Lexington
2.5 star property
Liberty Area
7.8 out of 10, Good, (843 reviews)
Set near restaurants and shops in Lexington, this traveler-friendly hotel offers a seasonal outdoor pool and 24-hour fitness center. Just a short drive from Kentucky Horse Park, Rupp Arena, and University of Kentucky, guests appreciate the helpful staff, clean rooms, free breakfast, and parking.
The price is $70
$81 total
includes taxes & fees
Jul 5 - Jul 6
Sleep Inn Lexington
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

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.
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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.

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 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.