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Hotels in Winchester

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Check prices for these dates

Tonight
Feb 4 - Feb 5
Tomorrow
Feb 5 - Feb 6
This weekend
Feb 6 - Feb 8
Next weekend
Feb 13 - Feb 15

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, (1,000 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 $72
$80 total
includes taxes & fees
Feb 9 - Feb 10
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, (775 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
Feb 8 - Feb 9
Baymont by Wyndham Winchester
Lobby
Hampton Inn Winchester
Hampton Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (456 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 $106
$117 total
includes taxes & fees
Feb 15 - Feb 16
Hampton Inn Winchester
Exterior
Holiday Inn Express Lexington East - Winchester by IHG
Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (541 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 $97
$107 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Express Lexington East - Winchester by IHG
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, (127 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
Mar 1 - Mar 2
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, (589 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 $62
$69 total
includes taxes & fees
Feb 8 - Feb 9
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, (354 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 $72
$80 total
includes taxes & fees
Feb 24 - Feb 25
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, (1,195 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 $87
$101 total
includes taxes & fees
Feb 5 - Feb 6
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Days Inn Lexington SE/Hamburg
Days Inn Lexington SE/Hamburg
2.0 star property
Lexington
7.2 out of 10, Good, (1,000 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 $59
$68 total
includes taxes & fees
Feb 10 - Feb 11
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, (736 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 $70
$81 total
includes taxes & fees
Feb 10 - Feb 11
Comfort Inn Lexington I-75
Reception
Hotel LEX, Trademark Collection by Wyndham
Hotel LEX, Trademark Collection by Wyndham
3.0 star property
Lexington
8.4 out of 10, Very Good, (584 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 $69
$80 total
includes taxes & fees
Feb 10 - Feb 11
Hotel LEX, Trademark Collection by Wyndham
Lobby
Hyatt Place Lexington
Hyatt Place Lexington
3.0 star property
Lexington
8.8 out of 10, Excellent, (1,002 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 $101
$117 total
includes taxes & fees
Feb 5 - Feb 6
Hyatt Place Lexington
Daily cooked-to-order breakfast for a fee
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 $88
$102 total
includes taxes & fees
Feb 20 - Feb 21
Holiday Inn Lexington - Hamburg by IHG
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, (901 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 $67
$78 total
includes taxes & fees
Feb 8 - Feb 9
avid hotel Lexington - Hamburg Area by IHG
Terrace/patio
Home2 Suites by Hilton Lexington Hamburg
Home2 Suites by Hilton Lexington Hamburg
3.0 star property
Lexington
9.4 out of 10, Exceptional, (1,002 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 $98
$113 total
includes taxes & fees
Feb 8 - Feb 9
Home2 Suites by Hilton Lexington Hamburg
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, (858 reviews)
The price is $89
$104 total
includes taxes & fees
Feb 10 - Feb 11
Hilton Garden Inn Lexington Hamburg
Free daily full breakfast
Homewood Suites Lexington-Hamburg
Homewood Suites Lexington-Hamburg
3.0 star property
Lexington
9.2 out of 10, Wonderful, (666 reviews)
Dive into comfort at this Lexington retreat with a 24-hour fitness center and outdoor pool. Enjoy free breakfast, WiFi, and parking while staying close to Kroger Field and Hamburg Pavilon. Clean rooms and helpful staff create a welcoming business-friendly atmosphere.
The price is $103
$119 total
includes taxes & fees
Feb 27 - Feb 28
Homewood Suites 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, (584 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 $89
$98 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Express & Suites Mt Sterling North by IHG
Lobby
GuestHouse Lexington
GuestHouse Lexington
2.5 star property
Lexington
8.4 out of 10, Very Good, (1,539 reviews)
The price is $71
$83 total
includes taxes & fees
Feb 10 - Feb 11
GuestHouse Lexington
Interior
Spark by Hilton Lexington Hamburg
Spark by Hilton Lexington Hamburg
2.5 star property
Lexington
8.6 out of 10, Excellent, (342 reviews)
Unwind in this peaceful retreat with easy highway access to downtown Lexington. The indoor pool and 24-hour fitness center offer perfect relaxation, while free breakfast, WiFi, and parking add value to your stay near Kroger Field and Kentucky Horse Park.
The price is $61
$70 total
includes taxes & fees
Feb 15 - Feb 16
Spark by Hilton Lexington Hamburg
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 pet-friendly hotels 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, (1000)
The price is $72
$80 total
includes taxes & fees
Feb 9 - Feb 10
Best Western Winchester Hotel
View all properties

You may also like hotels with pools in Winchester

Exterior
Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG

Holiday Inn Express Lexington East - Winchester by IHG
2.5 star property
Winchester
9.4 out of 10, Exceptional, (541)
The price is $97
$107 total
includes taxes & fees
Feb 8 - Feb 9
Holiday Inn Express Lexington East - Winchester by IHG
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 February
Currently viewing crowd sizes and weather for February.
Typical weather for Winchester
February
High 7°C / low -2°C. Cloudy most days.
View properties in February
7°
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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.
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18°
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April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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23°
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May, no crowd data, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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28°
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June, no crowd data, average high temperature 28 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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29°
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July, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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29°
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August, no crowd data, average high temperature 29 degrees Celsius, average low temperature 19 degrees Celsius. Sunny most days.
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26°
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September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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19°
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October, no crowd data, average high temperature 19 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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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°
weather_cloudy
December, no crowd data, average high temperature 8 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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4°
ac_unit
January, no crowd data, average high temperature 4 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
-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
Thanks to my friend of mine who's recommended me to this spot easy hike short walk to get there
Photo by Nawa Aseen
Open Photo by Nawa Aseen

Check out reviews of Winchester hotels guests love

Embassy Suites by Hilton Lexington/UK Coldstream

Embassy Suites by Hilton Lexington/UK Coldstream

10/10 Excellent
"All was good "
Olatunji 1-night trip
Posted 1 day ago
Embassy Suites by Hilton Lexington/UK Coldstream

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.