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Most frequently booked Winchester hotels

$99
Holiday Inn Express Lexington East - Winchester

Holiday Inn Express Lexington East - Winchester

2.5 out of 5.0 100 Winchester Plaza, Winchester, KY
4.8/5
(5 Reviews)
This hotel features an indoor pool and a 24-hour fitness center. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
 
$68
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5.0 1307 W Lexington Ave, Winchester, KY
3.9/5
(17 Reviews)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-out and a computer station are also provided.
 
$51
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5.0 960 Interstate Dr, Winchester, KY
3.4/5
(11 Reviews)
This hotel features an indoor pool and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Enjoy the spa tub and free perks like continental breakfast and free self parking.
 

Top cheap Winchester hotel deals

$51
Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5.0 960 Interstate Dr, Winchester, KY
3.4/5
(11 Reviews)
This hotel features an indoor pool and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Enjoy the spa tub and free perks like continental breakfast and free self parking.
 
$54
Red Roof Inn Lexington - Winchester

Red Roof Inn Lexington - Winchester

2.0 out of 5.0 1100 Interstate Drive, Winchester, KY
2.6/5
(11 Reviews)
This motel includes free WiFi in public areas and laundry facilities. Business travelers can take advantage of the business center. Staff at the 24-hour front desk can provide around-the-clock assistance.
 
$68
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5.0 1307 W Lexington Ave, Winchester, KY
3.9/5
(17 Reviews)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-out and a computer station are also provided.
 

Top luxury Winchester hotel deals

$68
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5.0 1307 W Lexington Ave, Winchester, KY
3.9/5
(17 Reviews)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Express check-out and a computer station are also provided.
Reviewed on Jul 20, 2020

Staff was very friendly. Great breakfast choices during COVID (I've seen some motels that typically serve breakfast use COVID as an excuse to not offer any options, so I really appreciate this motel going above and beyond to provide alternative options). The room was clean and bed was comfortable, ...

 
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How much is a hotel room in Winchester?

Hotels in Winchester start at $51 per night. Prices and availability subject to change. Additional terms may apply.

Winchester Hotel & Travel Guide

Since the days when it was a small town on the Western frontier, the power of the human character has driven Winchester, Kentucky to ever-greater achievements. Nestled amongst the rolling hills of the famed Bluegrass Region, the gorgeous scenery and down-to-earth locals will make you want to stay forever, while the inimitable pioneer spirit will also inspire you to see out great adventures from hotels in Winchester, KY.

Visiting Winchester

Are the scents of the day’s delicious meals already wafting through your curtains when you wake at Winchester hotels? It won’t be long until you indulge, but for now, follow the sounds of babbling brooks and gentle songbirds to Lower Howard’s Creek Nature and Heritage Preserve. In the spring, a sea of indigo overtakes the preserve as bluebells, Jacob’s ladder, and larkspur burst into color and friendly river otters wave hello from the riverbanks.

It will soon be time for sustenance, and Travelocity’s Winchester rental cars can take you on culinary pursuits to satisfy any palate. On the Beer Cheese Trail, let the delectable flavors of cheddar, beer and spices melt in your mouth—there is nothing on earth quite like Kentucky beer cheese, and you are lucky enough to be in its birthplace. Yearning for more? Whether you crave a classic, juicy American hot dog with all the accoutrements or fresh, country-style fish with more hush puppies than you can eat, Winchester’s Bypass Road is sure to satisfy.

Seventy-five miles west, Louisville also offers plenty of opportunity for edible adventures. While the flavors of smoky pulled pork linger in your mind, you sip a first-rate bourbon and let the toasted oak and caramel dance along your taste buds and warm your soul. After such exploits, you’ll be more than happy to slip under the covers at any of our superb Louisville hotels.

Thanks to the incredible souls who came before you and built their version of the American dream, no wish must remain unexplored in this Southern paradise. Book hotels near Winchester with Travelocity today, and your vacation fantasies can start coming true tomorrow.


Recent Winchester hotel reviews by fellow wanderers


*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.