Cheap Flights to Winchester from $75

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Winchester?

The cheapest prices found with in the last 7 days for return flights were $550 and $75 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
FCOSouthamptonMay 2 to May 6$550
YYZSouthamptonMay 11 to May 16$751
JFKSouthamptonMay 5 to May 9$923
BOSSouthamptonMay 3 to May 7$974
LAXSouthamptonMay 25 to June 3$1,032
SFOSouthamptonMay 4 to May 13$1,119
MELSouthamptonMay 1 to May 5$1,656
PEKChristchurchApril 30 to May 1$1,814
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKSouthamptonApril 25 to May 10$874
LAXSouthamptonApril 26 to May 12$1,155
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$550
Number of Airlines Serving
Airlines Serving
Aer Lingus
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Winchester Accommodation Deals

Days Inn by Wyndham Winchester M3

Days Inn by Wyndham Winchester M3

2.5 out of 5
Moto Motorway Service Area Winchester England
$39 nightly
The price is $47 total per night from Apr 26 to Apr 27
$47 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowDays Inn by Wyndham Winchester M3
 Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane Winchester England
$59 nightly
The price is $71 total per night from Apr 26 to Apr 27
$71 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (1,002 reviews)
Great hotel

Reviewed on Apr 16, 2026

Opens in a new window Marwell Hotel Winchester South
Winchester Royal Hotel

Winchester Royal Hotel

4 out of 5
St Peter Street Winchester England
$98 nightly
The price is $118 total per night from Apr 26 to Apr 27
$118 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy breakfast (surcharge), 24-hour room service, and parking (surcharge). Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
Great staff

Reviewed on Apr 18, 2026

Opens in a new windowWinchester Royal Hotel
Save an average of 15% on thousands of hotels when you're signed in
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
$102 nightly
The price is $123 total per night from Apr 30 to May 1
$123 total
Apr 30 - May 1
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
Clean room, lovely staff, gym was ok for a quick session,

Reviewed on Apr 9, 2026

Opens in a new windowThe Winchester Hotel & Spa
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.

Luxury Hotels in Winchester

Lainston House Hotel

Lainston House Hotel

3.5 out of 5
Woodman Lane Winchester England
Book a stay at this boutique hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Farley Mount Country Park and ...
Opens in a new windowLainston House Hotel
Hotel du Vin & Bistro Winchester

Hotel du Vin & Bistro Winchester

4 out of 5
Southgate Street Winchester England
$152 nightly
The price is $183 total per night from Apr 26 to Apr 27
$183 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
9/10 Wonderful! (566 reviews)
Lovely breakfast, wobblby tav

Reviewed on Apr 7, 2026

Opens in a new windowHotel du Vin & Bistro Winchester
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
$102 nightly
The price is $123 total per night from Apr 30 to May 1
$123 total
Apr 30 - May 1
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
Clean room, lovely staff, gym was ok for a quick session,

Reviewed on Apr 9, 2026

Opens in a new windowThe Winchester Hotel & Spa
Save an average of 15% on thousands of hotels when you're signed in
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way, Morn Hill Winchester England
$83 nightly
The price is $100 total per night from Apr 26 to Apr 27
$100 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (987 reviews)
Lovely staff. Clean room. Amazing breakfasts with loads of variety

Reviewed on Apr 21, 2026

Opens in a new windowvoco Winchester Hotel & Spa by IHG
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.

Family Friendly Hotels in Winchester

 Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane Winchester England
$59 nightly
The price is $71 total per night from Apr 26 to Apr 27
$71 total
Apr 26 - Apr 27
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
7.6/10 Good! (1,002 reviews)
Great hotel

Reviewed on Apr 16, 2026

Opens in a new window Marwell Hotel Winchester South
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way, Morn Hill Winchester England
$83 nightly
The price is $100 total per night from Apr 26 to Apr 27
$100 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (987 reviews)
Lovely staff. Clean room. Amazing breakfasts with loads of variety

Reviewed on Apr 21, 2026

Opens in a new windowvoco Winchester Hotel & Spa by IHG
The Running Horse

The Running Horse

4 out of 5
88 Main Road Winchester England
$70 nightly
The price is $84 total per night from May 4 to May 5
$84 total
May 4 - May 5
Total with taxes and fees
Book a stay at this business-friendly inn in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9/10 Wonderful! (333 reviews)
Overall, this hotel provided excellent value for money, combining comfort, convenience, and great service. I would definitely stay here again and recommend it to anyone looking for a pleasant and stress-free stay.

Reviewed on Apr 16, 2026

Opens in a new windowThe Running Horse
Save an average of 15% on thousands of hotels when you're signed in
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
$102 nightly
The price is $123 total per night from Apr 30 to May 1
$123 total
Apr 30 - May 1
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
Clean room, lovely staff, gym was ok for a quick session,

Reviewed on Apr 9, 2026

Opens in a new windowThe Winchester Hotel & Spa
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.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday
Don't see what you're looking for?
See all available trips from Boston to Winchester
View all trips

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Winchester?
Packed and ready to travel around the world? Hoping to begin in Winchester? A few of the 20 airlines that fly here include:

  • British Airways
  • Virgin Atlantic
  • Aer Lingus

What airport is best to fly into Winchester?
Before locking in your flight to Winchester, remember it has two airports. LHR is 45 mi from the city center, while Southampton Airport is 8 mi from the downtown area.
Where to stay in Winchester
Whether you're in Winchester on a family vacation, a solo adventure or something else entirely, you'll find the ideal place to lay your head. Book with Travelocity and pick from 203 properties within easy reach of the downtown area.If you're after somewhere fancy to spend your nights, slide between the silky smooth sheets at the Winchester Royal Hotel. Alternatively, look into the Days Inn by Wyndham Winchester M3. It's an attractive choice if you're vacationing on a smaller budget.
Places to visit in Winchester
If you want to check out a couple of the fabulous attractions here, add Great Hall, and Winchester Cathedral to your travel schedule.Winchester Christmas Market is a great place to buy yourself a gift or stroll among the stalls. Want some more options? Inject some culture into your stay by purchasing tickets to a play at Theatre Royal Winchester. And that's not all there is. You'll feel like you've stepped back in time with an excursion to Hospital of St Cross, a historically significant building.
How to get through airport security fast when traveling to Winchester
These useful tips and hints about airport security procedures will save you a lot of time and energy on your way to Winchester:

  • Be sure you know the whereabouts of your boarding pass and passport. You don't want to hold up the queue when you're asked to produce them.
  • Take off your belt, jewellery and shoes before approaching security. Items like these are not permitted to pass through the body scanner.
  • Laptops must be taken out of their protective cases and placed in a tub before being X-rayed.
  • Flying with a new cologne? As long as it contains no more than 3.4 ounces (100 milliliters) and it's stored in a clear resealable plastic bag, you can keep it with you in your hand luggage.
  • Steel-cap footwear and other heavy shoes are usually X-rayed at the security checkpoint. Consider wearing lightweight sneakers instead.
  • Some places have strict quarantine laws. Think about where you're headed to and whether or not you can travel with unpackaged foods.

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

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.