Create your free account
Sign in to your account
Get 24/7 travel help, thanks to our Customer First Guarantee
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Most Frequently Booked Winchester Hotels
Price for 1 night 2 adults*
Per night/room
Nov 3 - Nov 4
Red Roof Inn Lexington - Winchester
1100 Interstate Drive, Winchester, KYThis motel 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. The front desk is staffed around-the-clock and laundry facilities are on offer.
Per night/room
Oct 20 - Oct 21
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KYThis motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and express check-out are also provided.
Per night/room
Nov 1 - Nov 2
Hampton Inn Winchester
1025 Early Dr, Winchester, KYThis hotel features an outdoor pool and a fitness center. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Per night/room
Nov 3 - Nov 4
Holiday Inn Express Lexington East - Winchester
100 Winchester Plaza, Winchester, KYThis 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.
Top Cheap Winchester Hotel Deals
Price for 1 night 2 adults*
Baymont by Wyndham Winchester
960 Interstate Dr, Winchester, KYThis 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.
Per night/room
Nov 3 - Nov 4
Red Roof Inn Lexington - Winchester
1100 Interstate Drive, Winchester, KYThis motel 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. The front desk is staffed around-the-clock and laundry facilities are on offer.
Per night/room
Oct 20 - Oct 21
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KYThis motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and express check-out are also provided.
Top Luxury Winchester Hotel Deals
Price for 1 night 2 adults*
Per night/room
Oct 20 - Oct 21
Best Western Winchester Hotel
1307 W Lexington Ave, Winchester, KYThis motel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and express check-out are also provided.
Other Travelers Recently Booked These Winchester Hotels
Best Western Winchester Hotel 2.5 out of 5.0
How much is a hotel room in Winchester?
Hotels in Winchester start at $47 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
An Airport
An Attraction
- Hotels near Community Park
- Hotels near Southwind Golf Course
- Hotels near Clark Regional Medical Center
- Hotels near Bluegrass Heritage Museum
- Hotels near Lykins Park
- Hotels near Cassell Creek Golf Course
- Hotels near University of Kentucky
- Hotels near Rupp Arena
- Hotels near Keeneland Racing Course
- Hotels near Kroger Field
- Hotels near Mary Todd Lincoln House
- Hotels near Kentucky Horse Park
- Hotels near Red River Gorge
- Hotels near Fayette Mall
- Hotels near The Mall At Lexington Green
- Hotels near Lexington Opera House
- Hotels near Lexington Convention Center
- Hotels near Eastern Kentucky University
- Hotels near University of Kentucky Albert B. Chandler Hospital
- Hotels near Natural Bridge State Park
- Hotels near Georgetown College
- Hotels near Shriners Hospitals for Children
- Hotels near Lexington Public Library
- Hotels near Martin Castle
- Hotels near Transylvania University
- Hotels near Richmond Centre Mall
- Hotels near Fort Boonesborough State Park
- Hotels near Arboretum
- Hotels near Lexington Memorial Coliseum
- Hotels near Whitaker Bank Ballpark
- Hotels near The Red Mile Racetrack
- Hotels near Hummel Planetarium
- Hotels near EKU Center for the Arts
- Hotels near Jacobson Park
- Hotels near Talon Winery
- Hotels near Downtown Arts Center
- Hotels near Raven Run Nature Sanctuary
- Hotels near Lexington Ice Center
- Hotels near Thoroughbred Park
- Hotels near Masterson Station Park
- Georgetown Hotels
- Richmond Hotels
- Berea Hotels
- Slade Hotels
- Nicholasville Hotels
- Versailles Hotels
- Appalachian Mountains Hotels
- Mount Sterling Hotels
- Campton Hotels
- Paris Hotels
- Northern Kentucky Hotels
- Wilmore Hotels
- Carlisle Hotels
- Cynthiana Hotels
- Stanton Hotels
- Irvine Hotels
- Beattyville Hotels
- Lancaster Hotels
- Appalachian Plateau Hotels
- Owingsville Hotels
- Central United States Hotels
- The South Hotels
- Eastern Kentucky Hotels
- Clay City Hotels
- Ohio River Valley Hotels
- Salt Lick Hotels
- Frenchburg Hotels
- McKee Hotels
- Paint Lick Hotels
- Pine Ridge Hotels
- Bowen Hotels
- Waco Hotels
- Ravenna Hotels
- Flights to Winchester
The best fares to get you there
- Winchester Vacation Rentals
Great Deals on Alternative Accommodations
- Winchester Car Rentals
Affordable cars to get you around town
- Winchester Vacations
Save more by combining flights, hotels and cars
Most Popular
-
- Hotels with Jacuzzis In Room in Lexington
- Hotels in Shelbyville
- Hotels in Springfield
- Hotels in Central City
- Hotels in La Grange
- Hotels in Williamsburg
- Hotels in Mason
- Hotels in Liberty
- Hotels in Lawrenceburg
- Hotels in Dry Ridge
- Hotels in Henderson
- Hotels in Blue Ash
- Hotels in Batavia
- Hotels in Brooks
- Hotels in Marion
- Hotels in Frankfort
- Spa Resorts & Hotels in Lexington
- Pet Friendly Hotels in Lexington
- Capital Plaza Hotel
- Romantic Getaways & Hotels in Lexington
- Hotels with Jacuzzis In Room in Richmond
- Luxury Hotels in Lexington
- Boutique Hotels in Lexington
- Holiday Inn Express Nicholasville