Winchester Holidays
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Your Winchester Holiday
Take away the hard part of organising your next epic adventure with a Winchester holiday 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 holiday is just a few clicks away. Browse hotels, airfares and more on Expedia for an adventure that's tailored to suit your travel style.
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Blue Grass Airport (LEX) |
Population | 18,400 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Bluegrass Heritage Museum, Community Park and Lykins Park |
Top hotels in Winchester
Baymont by Wyndham Winchester
960 Interstate Dr Winchester KY
Fully refundableReserve now, pay when you stay
The price is £64 per night from 26 Jul to 27 Jul
£64
26 Jul - 27 Jul
includes taxes & fees
7.2/10 Good! (816 reviews)
"The staff was very friendly. Breakfast was good. Room clean and comfortable."
Reviewed on 26 Jun 2026
Value Stay
5100 Revilo Rd Winchester KY
Fully refundableReserve now, pay when you stay
The price is £54 per night from 29 Jun to 30 Jun
£54
29 Jun - 30 Jun
includes taxes & fees
7.6/10 Good! (158 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 14 Jun 2026
Marriott Lexington Griffin Gate Golf Resort & Spa
1800 Newtown Pike Lexington KY
Fully refundableReserve now, pay when you stay
The price is £106 per night from 29 Jun to 30 Jun
£106
29 Jun - 30 Jun
includes taxes & fees
8.4/10 Very good! (712 reviews)
"I absolutely love this hotel and it's location however it was my husband and my 15th anniversary and we wanted to stay for the weekend. The internet was down and we could not stream movies or shows and since it was pouring down rain and storming the entire time we couldn't use the pool or hottub ..."
Reviewed on 27 Jun 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.
Stay near popular Winchester attractions
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
£7
per adult
80% of travellers recommend
Unique Horse Farm Tours with Insider Access to Private Farms
£44
per adult
90% of travellers recommend
Lexington: Downtown Walking Food & History Tour
£74
per adult
100% of travellers recommend
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- Flights to Blue Grass
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- Flights to Kentucky
- Flights from Blue Grass
- Delta Detroit (DTW) to Lexington (LEX) flights
- Flights from Richmond
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- Flights from Paris
- Flights from Aberdeen (ABZ) to Lexington (LEX)
- Flights from Atlanta (ATL) to Lexington (LEX)
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- Flights from Birmingham (BHX) to Lexington (LEX)
- Flights from Nashville (BNA) to Lexington (LEX)
- Flights from Bristol (BRS) to Lexington (LEX)
- Flights from Baltimore (BWI) to Lexington (LEX)
- Flights from Columbia (CAE) to Lexington (LEX)
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- Flights from Dallas (DFW) to Lexington (LEX)
- Flights from Dublin (DUB) to Lexington (LEX)
- Flights from Edinburgh (EDI) to Lexington (LEX)
- Flights from Newark Liberty Intl. Airport (EWR) to Lexington (LEX)
- Flights from Guernsey (GCI) to Lexington (LEX)
- Flights from Glasgow (GLA) to Lexington (LEX)
- Flights from Washington (IAD) to Lexington (LEX)
- Flights from New York (JFK) to Lexington (LEX)
- Flights from London (LGW) to Lexington (LEX)
- Flights from London (LHR) to Lexington (LEX)
- Flights from Liverpool (LPL) to Lexington (LEX)
- Flights from Manchester (MAN) to Lexington (LEX)
- Flights from Kansas City (MCI) to Lexington (LEX)
- Flights from Orlando (MCO) to Lexington (LEX)
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- Flights from Minneapolis (MSP) to Lexington (LEX)
- Flights from Newcastle (NCL) to Lexington (LEX)
- Flights from Norwich (NWI) to Lexington (LEX)
- Flights from Chicago (ORD) to Lexington (LEX)
- Flights from Rapid City (RAP) to Lexington (LEX)
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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. Flight-inclusive packages are ATOL protected.
