Cheap Flight Deals to Winchester ENG from CA $667
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How to find cheap flights to Winchester?
The cheapest prices found with in the last 7 days for return flights were CA $959 and CA $667 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 | October 22 to October 28 | CA $959 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| YYZ | Southampton | August 1 to August 24 | CA $1,202 |
Your guide to flights to Winchester, ENG
Virgin Atlantic, Delta fly to Winchester, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winchester ENG currently costs between CA $959 and CA $1,202. Prices vary, but for the best fares, travel in January 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 $959. 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
"The shower was leaking and so the bathroom and floor of the room were wet/damp. There was a strong smell of mararjuna. The beds were comfortable though and it was good to have 2 singles with the double. Couldn't find any breakfast."
Reviewed on Jul 25, 2026
Marwell Hotel Winchester South
"Room was excellent, staff were very helpful. Only disappointment was the restaurant. Inflexible when ordering dessert (would not swap ice-cream for custard) and the breakfast was also slightly disappointing as there were only a limited choice (eg no sausages). However overall it was a very convenient ..."
Reviewed on Jul 25, 2026
Winchester Royal Hotel
"Potentially the best hotel we have ever stayed in, incredibly comfortable beds, very clean and well maintained rooms. Very relaxing surroundings and garden. The breakfast was delicious with an amazing choice. Parking available and in a perfect location to explore Winchester."
Reviewed on Jul 19, 2026
The Winchester Hotel & Spa
"Brilliant experience only down side was the hotels.com listing stated certain number of hotel parking spaces available but when arrived everything was chargeable and £10 for a stay between 5pm and 8am was very high"
Reviewed on Jul 30, 2026
Luxury Hotels in Winchester
Lainston House Hotel
Hotel du Vin & Bistro Winchester
The Winchester Hotel & Spa
"Brilliant experience only down side was the hotels.com listing stated certain number of hotel parking spaces available but when arrived everything was chargeable and £10 for a stay between 5pm and 8am was very high"
Reviewed on Jul 30, 2026
voco Winchester Hotel & Spa by IHG
"Not much great to say about this place other than the parking was good and it’s convenient for Winchester. The lift was not working so we had to haul our heavy bags on the stairs. Basement room smelled stuffy/lacking any fresh air. Breakfast was meh. Room was like a premier inn std."
Reviewed on Jul 26, 2026
Family Friendly Hotels in Winchester
Marwell Hotel Winchester South
"Room was excellent, staff were very helpful. Only disappointment was the restaurant. Inflexible when ordering dessert (would not swap ice-cream for custard) and the breakfast was also slightly disappointing as there were only a limited choice (eg no sausages). However overall it was a very convenient ..."
Reviewed on Jul 25, 2026
voco Winchester Hotel & Spa by IHG
"Not much great to say about this place other than the parking was good and it’s convenient for Winchester. The lift was not working so we had to haul our heavy bags on the stairs. Basement room smelled stuffy/lacking any fresh air. Breakfast was meh. Room was like a premier inn std."
Reviewed on Jul 26, 2026
The Running Horse
"Traveling from the USA , this is the second time we have stayed here visiting family in the area, great location , food and staff."
Reviewed on Jul 28, 2026
The Winchester Hotel & Spa
"Brilliant experience only down side was the hotels.com listing stated certain number of hotel parking spaces available but when arrived everything was chargeable and £10 for a stay between 5pm and 8am was very high"
Reviewed on Jul 30, 2026
Need a car after flight to Winchester?
Economy
Compact
Midsize
SUV
Frequently asked questions
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!
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in Southampton
- 4 Star Hotels in Winchester
- Chawton Hotels
- Hampshire Hotels
- Eastleigh Hotels
- Fareham Hotels
- Hotels near Hamble Common Beach
- B&B in Hythe
- Rv Parks in Micheldever
- Overton Hotels
- Hotels near Paultons Family Theme Park - Home of Peppa Pig World
- Romsey Hotels
- Sherfield English Hotels
- Hotels near Sir Harold Hillier Gardens
- Hotels near Southampton
- B&B in Southampton
- Condos in Southampton
- Hotels near Southampton Cruise Terminal
- Hotels near Southampton Guildhall
- Beach Resorts & in Southampton
- Kid Friendly Hotels in Southampton
- Golf Resorts & in Southampton
- Pet Friendly Hotels in Southampton
- Spa Resorts & in Southampton
- Hotel Wedding Venues Hotels in Southampton
- Southampton Hotels
- Houseboat Rentals in Southampton
- Vacation Homes in Southampton
- Hotels near St. Mary's Stadium
- Titchfield Hotels
- Hostels in Totton Station
- Hotels near Totton Station
- Hotels near University of Winchester
- Whitchurch Hotels
- Whiteley Hotels
- Hotels near Winchester Christmas Market
- Convention Center Hotels in Winchester
- Handpicked Hotels in Winchester
- Hotels with Hot Tubs in Winchester
- Pet Friendly Hotels in Winchester
- Winchester Hotels
- Flights to Southampton
- Air Canada Toronto (YYZ) to Southampton (SOU) flights
- Air Canada Montreal (YUL) to Southampton (SOU) flights
- Air Canada Vancouver (YVR) to Southampton (SOU) flights
- Air France Basel (BSL) to Southampton (SOU) flights
- Air France Paris (CDG) to Southampton (SOU) flights
- British Airways Dublin (DUB) to Southampton (SOU) flights
- British Airways Edinburgh (EDI) to Southampton (SOU) flights
- British Airways Limoges (LIG) to Southampton (SOU) flights
- Delta New York (JFK) to Southampton (SOU) flights
- Eastern Airways Manchester (MAN) to Southampton (SOU) flights
- Flybe Belfast (BHD) to Southampton (SOU) flights
- Icelandair Reykjavik (KEF) to Southampton (SOU) flights
- Klm Cape Town (CPT) to Southampton (SOU) flights
- Klm Ontario (ONT) to Southampton (SOU) flights
- Klm Amsterdam (AMS) to Southampton (SOU) flights
- United Roanoke (ROA) to Southampton (SOU) flights
- Flights from Amsterdam to Southampton
- Flights from Calgary to Winchester
- Flights from Vancouver to Southampton
- Flights from St. John's to Southampton
- Flights from Taiyuan to Southampton
- Flights from Cusco to Southampton
- Flights from Amsterdam (AMS) to Southampton (SOU)
- Flights from Bratislava (BTS) to Southampton (SOU)
- Flights from Zhengzhou (CGO) to Southampton (SOU)
- Flights from Detroit (DTW) to Southampton (SOU)
- Flights from Dublin (DUB) to Southampton (SOU)
- Flights from East Midlands (EMA) to Southampton (SOU)
- Flights from Isle of Man (IOM) to Southampton (SOU)
- Flights from London (LHR) to Southampton (SOU)
- Flights from Newcastle (NCL) to Southampton (SOU)
- Flights from San Juan (SJU) to Southampton (SOU)
- Flights from Vancouver (YVR) to Southampton (SOU)
- Flights from St. John's (YYT) to Southampton (SOU)
- Flights from Toronto (YYZ) to Southampton (SOU)