Cheap Flight Deals to Winchester VA from CA $186
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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 $161 and CA $186 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* |
|---|---|---|---|
| BOS | Baltimore | October 3 to October 5 | CA $161 |
| CLT | Chantilly | October 15 to October 19 | CA $223 |
| CLT | Washington | October 15 to October 19 | CA $223 |
| BOS | Washington | November 12 to November 13 | CA $226 |
| ATL | Chantilly | December 8 to December 15 | CA $234 |
| FLL | Washington | November 4 to November 7 | CA $301 |
| BOS | Chantilly | October 2 to October 3 | CA $329 |
| LAX | Chantilly | October 7 to October 11 | CA $389 |
| SFO | Washington | October 31 to November 7 | CA $518 |
| DFW | Washington | November 14 to November 17 | CA $520 |
| FLL | Chantilly | September 21 to September 26 | CA $566 |
| DFW | Baltimore | October 1 to October 5 | CA $608 |
| SFO | Baltimore | October 27 to November 11 | CA $665 |
| FCO | Chantilly | October 1 to October 5 | CA $736 |
| FCO | Baltimore | September 24 to October 3 | CA $1,073 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| FLL | Baltimore | September 11 to September 14 | CA $454 |
| FLL | Washington | September 11 to September 13 | CA $480 |
| ATL | Chantilly | September 12 to September 15 | CA $586 |
| BOS | Washington | September 11 to September 14 | CA $673 |
| BOS | Chantilly | September 11 to September 14 | CA $736 |
| DFW | Chantilly | September 13 to September 19 | CA $799 |
| DFW | Washington | September 11 to September 13 | CA $830 |
| DAL | Baltimore | September 13 to September 16 | CA $844 |
| LAX | Washington | September 11 to September 21 | CA $889 |
| LAX | Baltimore | September 12 to September 19 | CA $1,149 |
| ATL | Baltimore | September 11 to September 13 | CA $1,207 |
| SFO | Baltimore | September 12 to September 16 | CA $1,216 |
| SFO | Washington | September 13 to September 15 | CA $1,383 |
| SFO | Chantilly | September 11 to September 13 | CA $1,493 |
| BOS | Baltimore | September 12 to September 14 | CA $2,119 |
Your guide to flights to Winchester, VA
Air Canada 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 $161 and CA $2,119. Prices vary, but for the best fares, travel in October 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 $161. 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
Motel 6 Winchester, VA
"Stayed four nights and had no issues at all. Property was surprisingly quiet and pretty well maintained. Surrounding area was nice and felt safe with some good restaurants and convenience stores near by. Staff I encountered were friendly. For the price I paid, I have absolutely no complaints and ..."
Reviewed on Sep 8, 2026
Travelodge by Wyndham Winchester
"I stay here on a regular basis when I am in Winchester. Staff is great and if they have rooms available they let me check in early. That's not always the case but they will if its available."
Reviewed on Sep 8, 2026
Twi-Lite Inn
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
"Stayed four nights and had no issues at all. Property was surprisingly quiet and pretty well maintained. Surrounding area was nice and felt safe with some good restaurants and convenience stores near by. Staff I encountered were friendly. For the price I paid, I have absolutely no complaints and ..."
Reviewed on Sep 8, 2026
Travelodge by Wyndham Winchester
"I stay here on a regular basis when I am in Winchester. Staff is great and if they have rooms available they let me check in early. That's not always the case but they will if its available."
Reviewed on Sep 8, 2026
Wayside Inn
"It was a very nice room with very comfortable bed. We misplaced the key and they were very helpful getting a replacement after hours. Fortunately, we found the lost key. Staff bwas very pleasant. Air conditioner was a little loud but effective. Did not prevent from sleeping. Would stay again."
Reviewed on Aug 29, 2026
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
"Everything was great! Only odd thing was during one of the days there was an awful smell. The staff said it was the grease trap but it smelt like sewer or an overflowed toilet. Ended up leaving for a few hours and thankfully it was gone. Other then that it was a great stay and the kids loved being ..."
Reviewed on Sep 8, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
"Clean. Friendly and helpful staff. Good location. Safe."
Reviewed on Sep 6, 2026
Quality Inn Winchester
"Although the property was a little old and dated, the staff was very helpful and friendly! I found the entire property to be clean and the price and location were great."
Reviewed on Sep 8, 2026
Hampton Inn Front Royal
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Need a car after flight to Winchester?
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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!
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