Winchester Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿4,531 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Winchester
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is ฿5,256 per night from 22 Mar to 23 Mar
฿5,256
฿6,641 total
22 Mar - 23 Mar
includes taxes & fees
9.6/10 Exceptional! (1,181 reviews)
Remarkable MCM hotel with unique taste throughout. Friendly staff. Cozy bar, restaurant and lounge.
Reviewed on 2 Mar 2026
DoubleTree Suites by Hilton Hotel Lexington
2601 Richmond Rd Lexington KY
Fully refundableReserve now, pay when you stay
The price is ฿3,576 per night from 12 Mar to 13 Mar
฿3,576
฿4,151 total
12 Mar - 13 Mar
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Great staff!!
Reviewed on 2 Mar 2026
Hilton Lexington/Downtown
369 West Vine Street Lexington KY
Fully refundableReserve now, pay when you stay
The price is ฿4,684 per night from 31 Mar to 1 Apr
฿4,684
฿5,437 total
31 Mar - 1 Apr
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Of the 4 Hilton's I stay in regularly in KY and TN, this one has room for improvement. Building is very old and was the most luxurious of the downtown hotels. Unfortunately all that was lost during a bad renovation. Property is not a luxury hotel at all. Problems everywhere. Horrible wall paper pealing ...
Reviewed on 28 Feb 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
฿1,878
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
฿3,152
per adult
Experience Rebecca Ruth Chocolate Tour & Museum!
฿318
per adult
80% of travellers recommend
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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.
