Book Hotels in Winchester, KY
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Top Winchester hotels

The Manchester
The Manchester was a great experience. Its location is ideal. Unfortunately my stay was brief, checked in late and slept until right before checkout. I can only speak to the comfort of the rooms, which was excellent, and the courteousness of staff, also excellent. The atmosphere and ambiance are ...
Reviewed on Feb 5, 2026

Elwood Hotel & Suites
Staff, cleanliness, decor and location
Reviewed on Feb 1, 2026

Hampton Inn Winchester
Overall the hotel was good - very friendly staff, safe area, clean and presentable. I was quite surprised and astonished by the $75 pet fee - it is outrageous for adding a dog to add $75 to a $150 room. This also was not clearly presented during the booking process.
Reviewed on Jan 4, 2026

Home2 Suites by Hilton Lexington Hamburg
It was very clean. The staff at the desk, I can't remember the lady's name, was phenomenal. Was offered a room upgrade so I didn't have to use the pull out couch afterall. I appreciated that greatly. As for the rooms themselves, so spacious and well-equipped. Very convenient location with a lot of ...
Reviewed on Jan 24, 2026

Embassy Suites by Hilton Lexington Green
Excellent service!
Reviewed on Feb 2, 2026

DoubleTree Suites by Hilton Hotel Lexington
Very cool hotel, good amenities, clean, spacious good price really enjoyed it
Reviewed on Feb 2, 2026

Hyatt Regency Lexington
Fast check in, convenient location, clean
Reviewed on Feb 6, 2026

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Friendly staff, clean room, comfy bed
Reviewed on Feb 2, 2026

Hilton Lexington/Downtown
Nice quiet room. Staff were very helpful.
Reviewed on Jan 16, 2026
Cheap Winchester hotels

Baymont by Wyndham Winchester
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Winchester Hotel & Travel Guide\n
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.
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Recent Winchester hotel reviews by fellow wanderers

Hyatt Regency Lexington
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