Winchester Vacations from $555
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Your Winchester Vacation
Take away the hard part of organizing your next epic adventure with a Winchester vacation package. Whether you're visiting for its landmarks, food or other highlights, this city offers endless possibilities for fun. Every trip to Winchester needs a well-thought-out itinerary. Fill yours with attractions like Bluegrass Heritage Museum, Lykins Park and Southwind Golf Course. Your ultimate Winchester vacation is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Winchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Lex and Conference Center, Trademark Collection
Price was $630, price is now $555 per person
$555
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Lexington (LEX)
8/10 Very Good! (812 reviews)
I loved our stay here. The hotel is so cute, all this horse paraphernalia everywhere, fairy lights in the room - my daughters loved the fairy lights - good lighting in the bathroom for teenagers to put on their make up, the beds were comfy, full size refrigerator, and live music at the bar on one of the nights. We had a wonderful stay, I would go back and recommend it.
Reviewed on Oct 27, 2026
Stay near popular Winchester attractions
What to do in Winchester
Bites of the Bluegrass Cocktails & Bites Tour
$125
per adult
100% of travellers recommend
Distillery District Food & History Tour in Lexington
$125
per adult
Woodford Reserve, Castle & Key, and Stitzel Weller Bourbon Tour
$289
per adult
Winchester Hotel Deals
Comfort Inn Winchester
5250 Revilo Rd Winchester KY
Fully refundable
$69 nightly
The price is $76 total per night from Nov 17 to Nov 18
$76 total
Nov 17 - Nov 18
Total with taxes and fees
Value Stay
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
$53 nightly
The price is $59 total per night from Nov 11 to Nov 12
$59 total
Nov 11 - Nov 12
Total with taxes and fees
Quality Inn Lexington -Horse Park
1938 Stanton Way Lexington KY
Fully refundable
$59 nightly
The price is $68 total per night from Nov 23 to Nov 24
$68 total
Nov 23 - Nov 24
Total with taxes and fees
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.
Find the Best Winchester Vacation Packages
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 40ºF |
Max Temp Summer | 85ºF |
Top Sights | Bluegrass Heritage Museum, Southwind Golf Course and Lykins Park |
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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.
