Winchester Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Winchester
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is Rp3.323.351 per night from 31 May to 1 Jun
Rp3.323.351
Rp4.165.054 total
31 May - 1 Jun
includes taxes & fees
9.6/10 Exceptional! (1,289 reviews)
"Had a great overnight stay. Shuttle was great to Distillary area and dining room rooftop was nice. We even played Trivia that night ( ugh we lost). Great nights rest before heading to Nashville. Would stay there again for certain."
Reviewed on 18 May 2026
Hotel LEX, Trademark Collection by Wyndham
5532 Athens Boonesboro Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is Rp1.542.416 per night from 14 Jun to 15 Jun
Rp1.542.416
Rp1.790.283 total
14 Jun - 15 Jun
includes taxes & fees
8/10 Very Good! (705 reviews)
"The room was clean, but the lighting in the room was terrible. The rooms appeared newly remodeled but lacked modern lighting. The pool area was very nice, clean and big. Overall it was okay..would I stay there again? No"
Reviewed on 14 May 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is Rp1.696.128 per night from 31 May to 1 Jun
Rp1.696.128
Rp1.968.695 total
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (2,206 reviews)
"Love the plank flooring for traveling with a dog!"
Reviewed on 18 May 2026
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.
What to do in Winchester
Unique Horse Farm Tours with Insider Access to Private Farms
Rp1.023.414
per adult
90% of travellers recommend
Experience Rebecca Ruth Chocolate Tour & Museum!
Rp173.460
per adult
80% of travellers recommend
Seasonal Cooking and Entertaining with The Mischief Maker
Rp2.584.554
per adult
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
