Winchester Holidays from £1,020
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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.
Top Winchester Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Georgetown, KY
Price was £1,088, price is now £1,056 per person
£1,056
per person
1 Jun - 4 Jun
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Lexington (LEX)
8.8/10 Excellent! (1,008 reviews)
The staff, food was excellent and will stay here again.
Reviewed on 15 Apr 2026
Comfort Suites Georgetown
Price was £1,084, price is now £1,052 per person
£1,052
per person
1 Jun - 4 Jun
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Lexington (LEX)
8.6/10 Excellent! (1,002 reviews)
Didn't partake of breakfast other than a cup of yoghurt and a banana.
Reviewed on 10 Apr 2026
MainStay Suites Georgetown Lexington North
Price was £1,072, price is now £1,043 per person
£1,043
per person
1 Jun - 4 Jun
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Lexington (LEX)
7.4/10 Good! (223 reviews)
Clean and comfortable rooms. Easy to book and check-in, even with a last minute reservation.
Reviewed on 8 Apr 2026
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
Holiday Inn Express Lexington Horse Park Area by IHG
1935 Stanton Way, 1935 4 yes Lexington KY
Fully refundable
The price is £84 per night from 3 May to 4 May
£84
3 May - 4 May
includes taxes & fees
9.4/10 Exceptional! (2,168 reviews)
Clean property, professional staff and standard breakfast experience.
Reviewed on 14 Apr 2026
The Manchester
941 Manchester St Lexington KY
Fully refundableReserve now, pay when you stay
The price is £149 per night from 3 May to 4 May
£149
3 May - 4 May
includes taxes & fees
9.6/10 Exceptional! (1,236 reviews)
Awesome
Reviewed on 14 Apr 2026
Elwood Hotel & Suites
444 Parkway Drive Lexington KY
Fully refundableReserve now, pay when you stay
The price is £98 per night from 11 May to 12 May
£98
11 May - 12 May
includes taxes & fees
9.4/10 Exceptional! (1,075 reviews)
It was a 1-night stay. The young woman who checked us in was very friendly, explained how to get to the elevator, what amenities were available. The room was quite large, very clean, with a very comfortable bed. Would definitely recommend and hope to stay again.
Reviewed on 15 Apr 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.
Popular places to visit
Kentucky Horse Park
4.5/5(5 reviews)
Enjoy a trip to Kentucky Horse Park and popular activities such as horse riding in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
University of Kentucky
5/5(1 review)
Take a campus tour or just explore the area of University of Kentucky during your travels in Lexington. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Buffalo Trace Distillery
4/5(2 reviews)
You can take time to visit Buffalo Trace Distillery during your travels to Frankfort. You can seek out the hiking trails while in the area.
What to do in Winchester
Experience Rebecca Ruth Chocolate Tour & Museum!
£8
per adult
80% of travellers recommend
Lexington: Downtown Walking Food & History Tour
£74
per adult
Unique Horse Farm Tours with Insider Access to Private Farms
£44
per adult
90% 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. Flight-inclusive packages are ATOL protected.
