Cheap flights from Winchester

Many airlines offer flexible change policies

Earn BONUS+ rewards on top of your airline points

Enjoy exclusive promotions on the ebookers app!

Winchester Flight Information
Origin airport IATA code
LEX

Your cheap flight from Winchester is available right now.

Visit us now at Ebookers to choose from lots of cheap flights leaving Winchester or our last minute air tickets from Winchester at unbeatable prices, specially chosen for those who want the best deal possible. Ebookers continuously compares and updates the choice of air tickets available from Winchester, offered by more than 400 airlines worldwide. Ebookers works 24/7 to find the best deals so that our clients don’t have to waste their valuable time. Wherever you are going, you will find your perfect combination for a fantastic holiday at a budget price right here with our extensive flights database and helpful information; star ratings, reviews, maps and more… Many discount flights with a departure from Winchester and last minute flights from Winchester are available at Ebookers to help you organise your flights the way you want them at a price you can afford. Come and prepare your perfect holiday now at Ebookers.

Fancy a break from Winchester? Book your flight in advance from Winchester!

Thinking about getting away for a while and leaving from Winchester? Visit Ebookers and discover our selection of inexpensive Winchester flights and air tickets from Winchester at unbelievable prices with a great choice of airlines - over 400 in fact. We give excellent service at an affordable price. For a great weekend away from Winchester, visit to Ebookers where we have many available flights departing Winchester on special offer. Check out our deals and find a flight leaving Winchester at a price you never imagined. These special Ebookers offers aren’t just about cheap flights. We have over 95,000 hotels worldwide in our database, so why not stay in a Winchester hotel and start or end your break in style? Combine your choice of flight, hotel and car rental from our vast, reliable database to create your perfect holiday or dream weekend at a discounted price with Ebookers. Don’t wait or you may be too late!

Featured Hotels near Winchester

The Manchester

The Manchester

4 out of 5
941 Manchester St Lexington KY
The price is €177 per night from 1 Jul to 2 Jul
€177
1 Jul - 2 Jul
includes taxes & fees
Our customers tell us that they can't get enough of the comfortable beds at The Manchester . During your stay, you're just a quick walk from Lexington Brewing & Distilling Co.. Features include free WiFi in public areas, plus 2 restaurants and 2 bars. This property offers pet-friendly amenities, such as food and water bowls.
9.6/10 Exceptional! (1,309 reviews)
"This property is as advertised, a cool historic older B&B that’s got lots of character and is centrally located. The breakfast is solid and the Inn Keeper is a really nice guy who personalizes the experience. Their outdoor patio is very nice."

Reviewed on 5 Jun 2026

Opens in a new windowThe Manchester
Holiday Inn Express Lexington Horse Park Area by IHG

Holiday Inn Express Lexington Horse Park Area by IHG

3 out of 5
1935 Stanton Way, 1935 4 yes Lexington KY
The price is €90 per night from 4 Jul to 5 Jul
€90
4 Jul - 5 Jul
includes taxes & fees
The free breakfast at Holiday Inn Express Lexington Horse Park Area by IHG gets high marks from our customers. During your stay, you'll be close to Lexington Opera House. Enjoy features like free WiFi in public areas and free self-parking, plus an indoor pool.
9.4/10 Exceptional! (2,200 reviews)
"Hotel staff were great, the rooms were clean And the price was reasonable. Would definitely stay again."

Reviewed on 3 Jun 2026

Opens in a new windowHoliday Inn Express Lexington Horse Park Area by IHG
La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

La Quinta Inn & Suites by Wyndham Lexington South / Hamburg

3 out of 5
100 Canebrake Drive Lexington KY
The price is €91 per night from 14 Jun to 15 Jun
€91
14 Jun - 15 Jun
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at La Quinta Inn & Suites by Wyndham Lexington South / Hamburg. During your stay, you're just a quick walk from Lexington Sporting Club Youth Complex. Features include free WiFi in public areas and free self-parking, plus an indoor pool.
8.8/10 Excellent! (1,164 reviews)
"Room was fine, time to get new mattresses. Only 2.lottle runes of body wash in room. Sheets were clean but not that really nice clean smell."

Reviewed on 5 Jun 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Lexington South / Hamburg
Save an average of 15% on thousands of hotels when you're signed in
DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
2601 Richmond Rd Lexington KY
The price is €100 per night from 28 Jun to 29 Jun
€100
28 Jun - 29 Jun
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at DoubleTree Suites by Hilton Hotel Lexington. During your stay, you'll be within walking distance of Lexington Ice Center. You'll find features such as free WiFi in public areas and a free round-trip airport shuttle, plus an outdoor pool. This property offers pet-friendly amenities, such as food and water bowls.
8.8/10 Excellent! (1,009 reviews)
"Clean and staff was very helpful."

Reviewed on 4 Jun 2026

Opens in a new windowDoubleTree Suites by Hilton Hotel Lexington
Natural Bridge State Resort Park

Natural Bridge State Resort Park

3.5 out of 5
2135 Natural Bridge Road Slade KY
The price is €108 per night from 14 Jun to 15 Jun
€108
14 Jun - 15 Jun
includes taxes & fees
Our customers tell us that they can't get enough of the clean cabins at Natural Bridge State Resort Park. During your stay, you're just a quick walk from Hoedown Island. Features include free breakfast, free WiFi in public areas and free self-parking. This comfortable cabin has 46 cabins. Flat-screen TVs and coffee makers are available in all cabins.
8.6/10 Excellent! (1,911 reviews)
"Loved the location. Steps everywhere."

Reviewed on 5 Jun 2026

Opens in a new windowNatural Bridge State Resort Park
Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
1800 Newtown Pike Lexington KY
The price is €121 per night from 21 Jun to 22 Jun
€121
21 Jun - 22 Jun
includes taxes & fees
Our customers tell us that they can't get enough of the pool at Marriott Lexington Griffin Gate Golf Resort & Spa. During your stay, you'll be within walking distance of Eastern State Hospital. Enjoy features like free self-parking, plus a full-service spa and an indoor pool.
8.4/10 Very Good! (688 reviews)
"Quick stay. Staff was incredibly friendly. We had an issue with our air not working at night but couldn't move rooms (our choice) due our daughter being sound asleep. Staff was very apologetic and offered to get engineering to look at it. We declined until the morning to not wake the baby. They promptly ..."

Reviewed on 5 Jun 2026

Opens in a new windowMarriott Lexington Griffin Gate Golf Resort & Spa
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.