Winchester Vacation Packages
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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.
Top Winchester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Georgetown
Price was CA $1,140, price is now CA $1,045 per person
CA $1,045
per person
Aug 22 - Aug 28
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lexington (LEX)
8.4/10 Very Good! (1,001 reviews)
Very friendly staff, clean, good price. Would stay there again.
Reviewed on Jun 12, 2026
Holiday Inn Express Lexington North-Georgetown by IHG
Price was CA $1,339, price is now CA $1,265 per person
CA $1,265
per person
Aug 22 - Aug 28
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lexington (LEX)
8.8/10 Excellent! (747 reviews)
What you would expect. Which if fine
Reviewed on Jun 12, 2026
Country Inn & Suites by Radisson, Georgetown, KY
Price was CA $1,230, price is now CA $1,165 per person
CA $1,165
per person
Aug 22 - Aug 28
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lexington (LEX)
8.8/10 Excellent! (1,006 reviews)
Bathtub didn’t have a rubber mat in tub so very slippery. Toilet ran a lot, making noise often.
Reviewed on Jun 15, 2026
MainStay Suites Georgetown Lexington North
Price was CA $1,344, price is now CA $1,278 per person
CA $1,278
per person
Aug 22 - Aug 28
found 1 hour ago
Roundtrip non-stop flight included
Edmonton (YEG) to Lexington (LEX)
7.4/10 Good! (250 reviews)
I loved it was as advertised. Not many places still do that so my big family enjoyed that. However, my last morning I left my room(305) and went to my other room (303) with my mother. I went to go back in my room & the keys did not work. My children were still sleeping. It took two key resets, a maintenance man, 3 elevator rides, and almost an hour later to get this issue fixed once the master key reset the door lock. This was not a good experience and when I asked if I could have a discount for the inconvenience on a future stay I was told no. I got $10.
Reviewed on Jun 2, 2026
Winchester Hotel Deals
Value Stay
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
The price is CA $91 per night from Jun 17 to Jun 18
CA $91
CA $100 total
Jun 17 - Jun 18
includes taxes & fees
7.6/10 Good! (157 reviews)
"While the room was clean and maintained, the only grip I had was its location and the road you had to travel to reach the hotels. A sign would have been nice so drivers won't get lost on their first time getting to the hotel."
Reviewed on Jun 14, 2026
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Jul 12 to Jul 13
CA $112
CA $124 total
Jul 12 - Jul 13
includes taxes & fees
7.2/10 Good! (809 reviews)
"Great people clean rooms and the pool works"
Reviewed on Jun 8, 2026
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is CA $130 per night from Jul 2 to Jul 3
CA $130
CA $151 total
Jul 2 - Jul 3
includes taxes & fees
9.4/10 Exceptional! (2,200 reviews)
"I liked everything. Stayed one night in nice room with a very comfortable bed that I slept well in. Great breakfast selection. Will definitely return when in Lexington. Thanks"
Reviewed on Jun 16, 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.
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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.
