Cheap Flight Deals to Winchester VA from CA $144

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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 $112 and CA $144 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
ATLBaltimoreMay 10 to May 13CA $112
MCOBaltimoreApril 24 to April 27CA $124
LAXBaltimoreMay 1 to May 7CA $149
DFWBaltimoreApril 24 to April 28CA $155
ATLWashingtonMay 10 to May 13CA $225
TPABaltimoreApril 18 to April 22CA $250
ATLChantillyMay 10 to May 13CA $253
DALChantillyApril 12 to April 19CA $296
LAXChantillyMay 30 to June 3CA $327
LAXWashingtonMay 30 to June 3CA $327
MCOChantillyJune 5 to July 19CA $390
DENWashingtonApril 15 to May 3CA $401
SFOBaltimoreApril 26 to April 30CA $445
TPAChantillyApril 20 to April 21CA $730
BOSChantillyApril 24 to April 26CA $958
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXBaltimoreApril 5 to April 8CA $487
LAXChantillyApril 5 to April 8CA $680
LAXWashingtonApril 5 to April 8CA $686
SFOWashingtonApril 6 to April 9CA $747
SFOChantillyApril 5 to April 6CA $1,479
SFOBaltimoreApril 6 to April 9CA $8,004
*Prices include taxes and fees

Your guide to flights to Winchester, VA

WestJet 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 $112 and CA $8,004. Prices vary, but for the best fares, travel in June 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 $112. 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 August 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

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is CA $88 per night from Apr. 6 to Apr. 7
CA $88
CA $100 total
includes taxes & fees
Apr 6 - Apr 7
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,000 reviews)
Comfortable
"Nice stay. A few miles from I-81 as that was where I was traveling from NC to NY. It was clean and comfortable and a good place to walk the dog."

Reviewed on Mar. 27, 2025

Motel 6 Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is CA $91 per night from Apr. 20 to Apr. 21
CA $91
CA $99 total
includes taxes & fees
Apr 20 - Apr 21
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,104 reviews)
"Service was friendly & quick Room was super clean & smelled clean I felt safe because I observed desk clerk watching activity on cameras"

Reviewed on Mar. 30, 2025

Travelodge by Wyndham Winchester
Twi-Lite Inn

Twi-Lite Inn

2 out of 5
53 West 14th Street, Front Royal, VA
The price is CA $94 per night from Apr. 7 to Apr. 8
CA $94
CA $105 total
includes taxes & fees
Apr 7 - Apr 8
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8/10 Very Good! (501 reviews)
"Everything is clean,no bugs at all. I triple checked cause I’ve experienced bed bugs etc before. The blankets are thin and it’s close to a busy road that’s the worst parts. Owner and wife are nice.easy check in."

Reviewed on Mar. 4, 2025

Twi-Lite Inn
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Royal Inn Motel

Royal Inn Motel

2.5 out of 5
533 S. Royal Avenue, Front Royal, VA
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Blue Ridge Arts Council and Gallery and Front ...
6.4/10 (121 reviews)
Excellent for a roadside 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

Royal Inn Motel
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

Motel 6 Winchester, VA

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is CA $88 per night from Apr. 6 to Apr. 7
CA $88
CA $100 total
includes taxes & fees
Apr 6 - Apr 7
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,000 reviews)
Comfortable
"Nice stay. A few miles from I-81 as that was where I was traveling from NC to NY. It was clean and comfortable and a good place to walk the dog."

Reviewed on Mar. 27, 2025

Motel 6 Winchester, VA
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
The price is CA $91 per night from Apr. 20 to Apr. 21
CA $91
CA $99 total
includes taxes & fees
Apr 20 - Apr 21
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.2/10 Very Good! (1,104 reviews)
"Service was friendly & quick Room was super clean & smelled clean I felt safe because I observed desk clerk watching activity on cameras"

Reviewed on Mar. 30, 2025

Travelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is CA $148 per night from Apr. 14 to Apr. 15
CA $148
CA $178 total
includes taxes & fees
Apr 14 - Apr 15
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wayside ...
9.2/10 Wonderful! (376 reviews)
"Was a very fun atmosphere with and employees and also other guess very nice and friendly and excellent wings"

Reviewed on Feb. 2, 2025

Wayside Inn
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Hotel Strasburg

Hotel Strasburg

3 out of 5
213 S. Holliday Street, Strasburg, VA
Stay at this 3-star historic hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Shenandoah Valley Artworks and Strasburg ...
7.8/10 Good! (728 reviews)
awful
"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

Hotel Strasburg
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

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
The price is CA $126 per night from Apr. 6 to Apr. 7
CA $126
CA $137 total
includes taxes & fees
Apr 6 - Apr 7
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,002 reviews)
"Clean, comfortable, pool was nice, breakfast was good"

Reviewed on Apr. 2, 2025

Country Inn & Suites by Radisson, Winchester, VA
Fairfield Inn & Suites Strasburg Shenandoah Valley

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
The price is CA $154 per night from Apr. 14 to Apr. 15
CA $154
CA $171 total
includes taxes & fees
Apr 14 - Apr 15
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
"Pleasant hotel. Good staff. Breakfast was good. We had dinner at Blue Wing Frog Restaurant. 5 minute drive."

Reviewed on Mar. 26, 2025

Fairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn

Quality Inn

2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
The price is CA $122 per night from Apr. 10 to Apr. 11
CA $122
CA $132 total
includes taxes & fees
Apr 10 - Apr 11
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9/10 Wonderful! (1,003 reviews)
"Great place"

Reviewed on Mar. 29, 2025

Quality Inn
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Hampton Inn Front Royal

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA
The price is CA $145 per night from Apr. 27 to Apr. 28
CA $145
CA $161 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,001 reviews)
"Clean however was under renovation and informed after booking."

Reviewed on Apr. 2, 2025

Hampton Inn Front Royal
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.
Hilton Garden Inn Washington DC/U.S. Capitol
Airlie Hotel
Inn at Evergreen
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Need a car after flight to Winchester?

Frequently asked questions

Which airlines fly to Winchester?
Whether you’re seeking first-rate service or tasty in-flight meals on your flight to Winchester, you’re bound to find what you’re looking for. There are 20 carriers that advertise flights to this city, including:

  • United Airlines
  • American Airlines
  • Delta Air Lines

Where to stay in Winchester
Few things are as satisfying as sliding into bed after a big day of sightseeing. With an impressive 45 accommodations in Winchester, you can have your pick of the comfiest of them.The The George Washington Hotel, A Wyndham Grand Hotel and the City Charmer Near Historic Oldtown Winchester are some of Travelocity’s top accommodation options in the Winchester area.
Places to visit in Winchester
0 Seeking some more options? 0 But that’s not all there is. 0
How to get through airport security fast when traveling to Winchester
Make your flight to Winchester a little easier by following these useful security tips:

  • Have your travel ID and boarding pass within easy reach. They’ll be the first things you’ll be instructed to produce by airport security staff.
  • You’ll need to put your tunes on pause for a little while. Earphones and headphones must be removed and put in a tray for X-raying. The same goes for items such as belts and heavy jackets.
  • Laptops need to be taken out of their protective carry bags and placed in a tray before going through the X-ray machine.
  • Toothpaste, lip balm and other toiletry items in gel, liquid or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They must also fit in a 1-quart (1-liter) clear zip-lock bag.
  • Think about the type of footwear you want to travel in. Slippers are awesome because they’re a cinch to step out of when you’re at the security checkpoint. Try wearing a pair on your next flight!
  • Some places have strict quarantine laws. Consider where you’re going to and whether or not you’re permitted to travel with fruit and meats.

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!

*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.