Cheap Flight Deals to Winchester VA from CA $196
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 $120 and CA $196 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* |
|---|---|---|---|
| FLL | Baltimore | January 7 to January 9 | CA $128 |
| FLL | Washington | January 8 to January 12 | CA $130 |
| DFW | Baltimore | January 10 to January 14 | CA $157 |
| BOS | Washington | January 7 to January 14 | CA $193 |
| ATL | Baltimore | January 24 to January 25 | CA $197 |
| MCO | Washington | February 19 to February 25 | CA $199 |
| LAX | Baltimore | December 25 to January 1 | CA $357 |
| SFO | Washington | January 31 to February 6 | CA $365 |
| SFO | Chantilly | January 8 to January 14 | CA $422 |
| CLT | Chantilly | December 19 to December 21 | CA $438 |
| SFO | Baltimore | January 8 to January 12 | CA $605 |
| LAX | Chantilly | December 25 to January 1 | CA $608 |
| FCO | Chantilly | January 17 to January 24 | CA $691 |
| FCO | Baltimore | January 17 to January 30 | CA $905 |
| FCO | Washington | January 17 to January 30 | CA $930 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| FLL | Baltimore | December 12 to December 15 | CA $120 |
| MCO | Baltimore | December 13 to December 14 | CA $129 |
| BOS | Washington | December 12 to December 14 | CA $235 |
| FLL | Washington | December 12 to December 15 | CA $266 |
| DFW | Baltimore | December 12 to December 18 | CA $350 |
| BOS | Chantilly | December 13 to December 14 | CA $351 |
| MCO | Washington | December 13 to December 14 | CA $382 |
| ATL | Baltimore | December 13 to December 14 | CA $500 |
| FCO | Chantilly | December 14 to December 16 | CA $1,740 |
Your guide to flights to Winchester, VA
Delta, Porter Airlines 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 VA currently costs between CA $120 and CA $1,740. Prices vary, but for the best fares, travel in February 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 $120. 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 December 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
Motel 6 Winchester, VA
Good area
Reviewed on Nov 26, 2025
Travelodge by Wyndham Winchester
Room clean, heater works great parking
Reviewed on Dec 7, 2025
Twi-Lite Inn
Room was very clean. Easy, efficient check-in, quiet, very comfortable beds.
Reviewed on Nov 23, 2025
Royal Inn Motel
It’s a roadside motel. Extremely cheap. For the price- it was excellent. Beds comfortable enough. Not enough towels. No toiletries besides soap. NO COFFEE MAKER. That was strange. BUT the room was big and had fridge and microwave. Overall very happy.
Reviewed on Dec 23, 2020
Luxury Hotels in Winchester
Motel 6 Winchester, VA
Good area
Reviewed on Nov 26, 2025
Travelodge by Wyndham Winchester
Room clean, heater works great parking
Reviewed on Dec 7, 2025
Wayside Inn
Brittany and the rest of the staff at Wayside were wonderful. They made us feel welcome, talked to us about the history and quirks of the, and our room was very quaint. The Christmas decorations in the room were a nice touch.
Reviewed on Nov 23, 2025
Hotel Strasburg
The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!
Reviewed on Oct 5, 2020
Family Friendly Hotels in Winchester
Country Inn & Suites by Radisson, Winchester, VA
Average room, very clean. Breakfast was disappointing.
Reviewed on Dec 2, 2025
Fairfield Inn & Suites Strasburg Shenandoah Valley
Everything was wonderful, especially the mattress which appeared new and was very firm but soft on top.
Reviewed on Nov 2, 2025
Quality Inn Winchester
Everything was great, including breakfast
Reviewed on Dec 6, 2025
Hampton Inn Front Royal
Everything was great about this Hampton Inn. It's dog friendly so i didn't know what to expect. It was very clean, nicely decorated (not dated) and the staff was super nice. Highly recommend it.
Reviewed on Dec 4, 2025
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
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!
Need more than a Flight to Winchester?
Near Winchester
Other Flights to Winchester
Most Popular
- Spa Resorts & Hotels in Woodbridge
- Hotels in Grand Forks
- Kid Friendly Hotels in Virginia Beach
- Hotels in Syria
- Hotels in Great Falls
- Beach Resorts & Hotels in Virginia Beach
- Hotels in Virginia Beach
- Hotels in Palm Desert
- Hotels in Fargo
- Hotels in Honolulu
- Hotels in Staunton
- Hotels in Duluth
- Hotels in Niagara Falls
- Hotels in Bangor
- Hotels in Kalispell