Hotels in Winchester

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Check prices for these dates

Tonight
Apr 17 - Apr 18
Tomorrow
Apr 18 - Apr 19
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 22 - Apr 23
Best Western Winchester Hotel
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, (136 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 19 - Apr 20
Value Stay
Indoor pool
Baymont by Wyndham Winchester
Baymont by Wyndham Winchester
2.5 star property
Winchester
7.2 out of 10, Good, (787 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 $80
$88 total
includes taxes & fees
Apr 30 - May 1
Baymont by Wyndham Winchester
Lobby
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (462 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 $128
$141 total
includes taxes & fees
May 10 - May 11
Hampton Inn Winchester
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 21 - Apr 22
Red Roof Inn Winchester - Lexington East
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 $124
$137 total
includes taxes & fees
Apr 30 - May 1
Holiday Inn Express Lexington East - Winchester by IHG
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 $76
$83 total
includes taxes & fees
May 12 - May 13
Comfort Inn Winchester
Indoor pool, sun loungers
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, (1,141 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 $95
$110 total
includes taxes & fees
Apr 19 - Apr 20
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Lobby
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,010 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 $58
$67 total
includes taxes & fees
May 19 - May 20
Days Inn Lexington SE/Hamburg
Lobby
Comfort Inn Lexington I-75
Comfort Inn Lexington I-75
2.5 star property
Lexington
7.4 out of 10, Good, (752 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 $75
$87 total
includes taxes & fees
May 10 - May 11
Comfort Inn Lexington I-75
Reception
Hotel LEX, Trademark Collection by Wyndham
Hotel LEX, Trademark Collection by Wyndham
3.0 star property
Lexington
8.2 out of 10, Very Good, (663 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 $84
$98 total
includes taxes & fees
Apr 27 - Apr 28
Hotel LEX, Trademark Collection by Wyndham
Exterior
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, (932 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 $88
$103 total
includes taxes & fees
Apr 19 - Apr 20
avid hotel Lexington - Hamburg Area by IHG
Lobby
Hyatt Place Lexington
Hyatt Place Lexington
3.0 star property
Lexington
8.6 out of 10, Excellent, (1,004 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 $110
$128 total
includes taxes & fees
Apr 27 - Apr 28
Hyatt Place Lexington
Exterior
Holiday Inn Lexington - Hamburg by IHG
Holiday Inn Lexington - Hamburg by IHG
3.0 star property
Lexington
9.0 out of 10, Wonderful, (1,002 reviews)
The price is $100
$116 total
includes taxes & fees
May 19 - May 20
Holiday Inn Lexington - Hamburg by IHG
Breakfast and dinner served, American cuisine
Hilton Garden Inn Lexington Hamburg
Hilton Garden Inn Lexington Hamburg
3.0 star property
Liberty Area
8.6 out of 10, Excellent, (885 reviews)
The price is $111
$128 total
includes taxes & fees
May 14 - May 15
Hilton Garden Inn Lexington Hamburg
Snack bar
Tru By Hilton Lexington Hamburg
Tru By Hilton Lexington Hamburg
2.5 star property
Liberty Area
9.4 out of 10, Exceptional, (198 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 $104
$121 total
includes taxes & fees
May 4 - May 5
Tru By Hilton Lexington Hamburg
Terrace/patio
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (1,001 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
May 3 - May 4
Home2 Suites by Hilton Lexington Hamburg
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, (603 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 $125
$138 total
includes taxes & fees
Apr 26 - Apr 27
Holiday Inn Express & Suites Mt Sterling North by IHG
Lobby lounge
Sleep Inn Lexington
Sleep Inn Lexington
2.5 star property
Liberty Area
7.8 out of 10, Good, (827 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 $75
$86 total
includes taxes & fees
May 15 - May 16
Sleep Inn Lexington
Indoor pool
Comfort Inn & Suites Mount Sterling
Comfort Inn & Suites Mount Sterling
2.5 star property
Mount Sterling
7.8 out of 10, Good, (736 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 $99
$110 total
includes taxes & fees
Apr 30 - May 1
Comfort Inn & Suites Mount Sterling
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 family-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, (136)
The price is $48
$53 total
includes taxes & fees
Apr 19 - Apr 20
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

3.7/5 (13 reviews)
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.

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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

Holiday Inn Lexington - Hamburg by IHG

Holiday Inn Lexington - Hamburg by IHG

8/10 Good
"Clean room, good location. Nice bar with restaurant"
Mark 1-night trip
Posted 8 hours ago
Holiday Inn Lexington - Hamburg by IHG

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.