Cheap Flight Deals to Winchester ENG from CA $64
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How to find cheap flights to Winchester?
The cheapest prices found with in the last 7 days for return flights were CA $193 and CA $64 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| YYZ | Southampton | November 19 to December 4 | CA $989 |
| BOS | Southampton | October 29 to November 2 | CA $1,512 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| YYZ | Southampton | October 23 to October 25 | CA $1,798 |
Your guide to flights to Winchester, ENG
easyJet, Jet2, Air Canada, Delta fly to Winchester, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winchester ENG currently costs between CA $193 and CA $1,798. Prices vary, but for the best fares, travel in December when prices are at their lowest.
Top tips for finding cheap flights to Winchester
The cheapest flight for a round trip to Winchester is currently CA $193. When you search for flights to Winchester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winchester for nearby days. The cheapest month to travel to Winchester is October from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Winchester
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Winchester with Travelocity
We have top deals on plane tickets even for last minute flights to Winchester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winchester for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Winchester
Days Inn by Wyndham Winchester M3
"Incredibly basic and room needed a dust / window mould removed. However, it's fine for the price and just a few steps walk to the services. Staff are only a phonecall away and very quick to bring extra pillows, fan etc. Just be aware, if you're using as a base to get to and from Winchester, it's ..."
Reviewed on Oct 18, 2026
Marwell Hotel Winchester South
"The location was excellent 👍 Very quiet and breakfast was delicious."
Reviewed on Oct 11, 2026
Winchester Royal Hotel
"Comfortable room and helpful staff"
Reviewed on Oct 12, 2026
The Winchester Hotel & Spa
"A lovely hotel with amazing staff who tend to your every need. Spa is lovely and treatments are out of this world. Food and service is 5star. This hotel is the perfect location as it’s walking distance from Winchester city centre. Perfect for a few days away to relax"
Reviewed on Oct 19, 2026
Luxury Hotels in Winchester
Lainston House Hotel
"Beautiful rooms - we even had a TV in the bathroom, and the staff were not only very helpful but always had time for us and were happy to tell me about the hotel, its history and the activities which go on there, such as cookery school. There were some great touches, such as the light controls by ..."
Reviewed on Oct 16, 2026
Hotel du Vin & Bistro Winchester
The Winchester Hotel & Spa
"A lovely hotel with amazing staff who tend to your every need. Spa is lovely and treatments are out of this world. Food and service is 5star. This hotel is the perfect location as it’s walking distance from Winchester city centre. Perfect for a few days away to relax"
Reviewed on Oct 19, 2026
voco Winchester Hotel & Spa by IHG
Family Friendly Hotels in Winchester
Marwell Hotel Winchester South
"The location was excellent 👍 Very quiet and breakfast was delicious."
Reviewed on Oct 11, 2026
voco Winchester Hotel & Spa by IHG
The Running Horse
"The room was very clean and comfortable and had all the little extras including ironing board and hairdryer as well as fresh milk for the tea/coffee provided. Also the all necessary toiletries. The staff were also very friendly and helpful."
Reviewed on Oct 10, 2026
The Winchester Hotel & Spa
"A lovely hotel with amazing staff who tend to your every need. Spa is lovely and treatments are out of this world. Food and service is 5star. This hotel is the perfect location as it’s walking distance from Winchester city centre. Perfect for a few days away to relax"
Reviewed on Oct 19, 2026
Need a car after flight to Winchester?
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Plane Tickets To Winchester
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winchester today!
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