Cheap Flights to Winchester from $287
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 Much Does it Cost To Fly To Winchester?
The cheapest prices found with in the last 7 days for return flights were $621 and $287 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
BOS
Logan Intl.
SOU
Southampton
$621 Roundtrip, found 4 days ago
$621
Roundtrip
found 4 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | Southampton | January 11 to January 25 | $621 |
| JFK | Southampton | January 10 to January 25 | $622 |
| YYZ | Southampton | March 24 to April 8 | $695 |
| LAX | Southampton | January 12 to January 25 | $748 |
| SFO | Southampton | January 18 to January 26 | $768 |
| FCO | Southampton | December 31 to January 4 | $824 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Southampton | December 19 to December 23 | $2,009 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $621 |
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
Moto Motorway Service Area Winchester England
$39 nightly
The price is $47 total per night from Dec 23 to Dec 24
$47 total
Dec 23 - Dec 24
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 ...
7.2/10 Good! (838 reviews)
Everything was clean and good With the respected employee
Reviewed on Nov 2, 2025
Marwell Hotel Winchester South
Thompson Lane Winchester England
$64 nightly
The price is $77 total per night from Jan 3 to Jan 4
$77 total
Jan 3 - Jan 4, 2026
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! (1,004 reviews)
Yes good
Reviewed on Dec 15, 2025
Winchester Royal Hotel
St Peter Street Winchester England
$122 nightly
The price is $146 total per night from Jan 12 to Jan 13
$146 total
Jan 12 - Jan 13, 2026
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 ...
8.2/10 Very Good! (1,000 reviews)
We had one breakfast during our 2 day spell which was excellent
Reviewed on Dec 9, 2025
Save an average of 15% on thousands of hotels when you're signed in
The Winchester Hotel & Spa
Worthy Lane Winchester England
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 ...
8.4/10 Very Good! (1,003 reviews)
Staff were excellent, Oakley was brilliant at the front desk- rooms were lovely and facilities amazing - will be back
Reviewed on Dec 14, 2025
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
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 ...
Stately home from home
Very nice stay in a stately home. Staff are extremely friendly and helpful, and the food is high quality
Reviewed on Feb 12, 2022
Hotel du Vin & Bistro Winchester
Southgate Street Winchester England
$118 nightly
The price is $142 total per night from Jan 4 to Jan 5
$142 total
Jan 4 - Jan 5, 2026
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 ...
8.8/10 Excellent! (547 reviews)
A very pleasant two-night stay in a convenient location in Winchester. Good value for money given its premium look and feel. My only concern was confusion over the way my credit card was loaded on check-in with the full cost of the booking + another almost full day.
Reviewed on Dec 5, 2025
The Winchester Hotel & Spa
Worthy Lane Winchester England
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 ...
8.4/10 Very Good! (1,003 reviews)
Staff were excellent, Oakley was brilliant at the front desk- rooms were lovely and facilities amazing - will be back
Reviewed on Dec 14, 2025
Save an average of 15% on thousands of hotels when you're signed in
voco Winchester Hotel & Spa by IHG
Telegraph Way Morn Hill Winchester England
$91 nightly
The price is $110 total per night from Jan 4 to Jan 5
$110 total
Jan 4 - Jan 5, 2026
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! (931 reviews)
Really good hotel, great staff and very clean, well equipped. There were some issues, seemed really understaffed the first two nights, so quite long waits at the bar a, but the bit that really got my goat was the bwto be sergeant major
Reviewed on Dec 11, 2025
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
Thompson Lane Winchester England
$64 nightly
The price is $77 total per night from Jan 3 to Jan 4
$77 total
Jan 3 - Jan 4, 2026
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! (1,004 reviews)
Yes good
Reviewed on Dec 15, 2025
voco Winchester Hotel & Spa by IHG
Telegraph Way Morn Hill Winchester England
$91 nightly
The price is $110 total per night from Jan 4 to Jan 5
$110 total
Jan 4 - Jan 5, 2026
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! (931 reviews)
Really good hotel, great staff and very clean, well equipped. There were some issues, seemed really understaffed the first two nights, so quite long waits at the bar a, but the bit that really got my goat was the bwto be sergeant major
Reviewed on Dec 11, 2025
The Running Horse
88 Main Road Winchester England
$50 nightly
The price is $60 total per night from Jan 11 to Jan 12
$60 total
Jan 11 - Jan 12, 2026
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! (306 reviews)
Lovely cosy room, nice touch with the homemade short bread and the Christmas music playing. Thank you so much
Reviewed on Dec 14, 2025
Save an average of 15% on thousands of hotels when you're signed in
The Winchester Hotel & Spa
Worthy Lane Winchester England
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 ...
8.4/10 Very Good! (1,003 reviews)
Staff were excellent, Oakley was brilliant at the front desk- rooms were lovely and facilities amazing - will be back
Reviewed on Dec 14, 2025
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.
Need a Car For After Your Flight?
Economy
Chevrolet Spark or similar
Compact
Ford Focus or similar
Midsize
Toyota Corolla or similar
SUV
Jeep Compass or similar
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
- Cottages in Micheldever
- Micheldever Hotels
- All Inclusive Resorts & in Hampshire
- Hotels with Free Breakfast in Hampshire
- Hotels with smoking rooms in Hampshire
- Hotels on the River in Hampshire
- Romantic Getaways & Hotels in Hampshire
- Waterpark Hotels and Resorts in Hampshire
- Hampshire Hotels
- Cabins in Hampshire
- Extended Stay Hotels in Hampshire
- Hotels near Winchester Christmas Market
- Hursley Hotels
- Kings Worthy Hotels
- Cheriton Hotels
- B&B in Itchen Abbas
- Chandler's Ford Hotels
- Hotels near Southampton
- Eastleigh Hotels
- Hinton Ampner Hotels
- Sutton Scotney Hotels
- Hotels near Sparsholt College
- Hotels near Sir Harold Hillier Gardens
- Hotels near Winchester Cathedral
- Hotels near Winchester Science Centre and Planetarium
- Ampfield Hotels
- Flights to Gosport
- Flights to Woodlands
- Flights to Basingstoke
- Flights to Rogate
- Flights to Denmead
- Flights to Hampshire
- Flights to Barton Stacey
- Flights to Salisbury
- Flights to Tadley
- Flights to Monk Sherborne
- Flights to Southampton
- Flights to Alderbury
- Flights to Kingsclere
- Flights to Beaulieu
- Flights to Cowes
- Flights to Romsey
- Flights to Liss
- Flights to Clanfield
- Flights to Havant
- Flights to Emsworth
- Flights from Southampton
- Air Canada Toronto (YYZ) to Southampton (SOU) flights
- Air France Paris (CDG) to Southampton (SOU) flights
- American Airlines Dallas (DFW) to Southampton (SOU) flights
- American Airlines New York (JFK) to Southampton (SOU) flights
- British Airways Edinburgh (EDI) to Southampton (SOU) flights
- British Airways Rome (FCO) to Southampton (SOU) flights
- British Airways Houston (IAH) to Southampton (SOU) flights
- British Airways New York (JFK) to Southampton (SOU) flights
- British Airways Newcastle (NCL) to Southampton (SOU) flights
- British Airways Seattle (SEA) to Southampton (SOU) flights
- British Airways Phoenix (PHX) to Southampton (SOU) flights
- Delta Atlanta (ATL) to Southampton (SOU) flights
- Eastern Airways Manchester (MAN) to Southampton (SOU) flights
- Flybe Belfast (BHD) to Southampton (SOU) flights
- Flybe Glasgow (GLA) to Southampton (SOU) flights
- Flybe Leeds (LBA) to Southampton (SOU) flights
- Klm Amsterdam (AMS) to Southampton (SOU) flights
- Flights from Nashville (BNA) to Southampton (SOU)
- Flights from Boston (BOS) to Southampton (SOU)
- Flights from Charlotte (CLT) to Southampton (SOU)
- Flights from Dublin (DUB) to Southampton (SOU)
- Flights from Newark Liberty Intl. Airport (EWR) to Southampton (SOU)
- Flights from Los Angeles (LAX) to Southampton (SOU)
- Flights from London (LHR) to Southampton (SOU)
- Flights from Orlando (MCO) to Southampton (SOU)
- Flights from Miami (MIA) to Southampton (SOU)
- Flights from Chicago (ORD) to Southampton (SOU)
- Flights from Portland (PDX) to Southampton (SOU)
- Flights from Philadelphia (PHL) to Southampton (SOU)
- Flights from Phoenix (PHX) to Southampton (SOU)
- Flights from Pittsburgh (PIT) to Southampton (SOU)
- Flights from Raleigh (RDU) to Southampton (SOU)
- Flights from Fort Myers (RSW) to Southampton (SOU)
- Flights from San Francisco (SFO) to Southampton (SOU)
- Flights from Tampa (TPA) to Southampton (SOU)
- Flights to Hook
- Flights to Horndean
- Flights to Amesbury
- Flights to Eastleigh
- Flights to Petersfield
- Flights to Brockenhurst
- Flights to Tidworth
- Flights to Privett
- Flights to Stony Cross
- Flights to Otterbourne