Cheap Flight Deals to Winchester VA from CA $170

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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 $110 and CA $170 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Tue., Jun. 24 - Tue., Sep. 23
YTZ
Billy Bishop Toronto City
IAD
Washington Dulles Intl.
CA $270 Roundtrip, found 2 days ago
CA $270
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue., Jun. 24 from Billy Bishop Toronto City to Washington Dulles Intl., returning Tue., Sep. 23, priced at CA $270 found 2 days ago
OriginDestinationTravel datesFlights from*
ATLBaltimoreJune 14 to June 17CA $110
DFWBaltimoreJune 16 to June 24CA $111
BOSBaltimoreJune 12 to June 16CA $120
MCOBaltimoreJune 13 to June 16CA $138
LAXBaltimoreJune 26 to July 3CA $139
ATLChantillySeptember 3 to September 9CA $190
MCOWashingtonJuly 4 to July 4CA $214
MIABaltimoreJune 14 to June 15CA $216
BOSChantillyJuly 1 to July 4CA $339
DENBaltimoreJuly 25 to August 4CA $361
ATLWashingtonJune 7 to June 14CA $384
LAXChantillyAugust 15 to August 17CA $396
LAXWashingtonAugust 23 to August 31CA $414
DENChantillyJune 14 to June 16CA $500
DENWashingtonJune 10 to June 14CA $647
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
ATLBaltimoreJune 7 to June 9CA $116
LAXBaltimoreJune 7 to June 8CA $374
ATLWashingtonJune 7 to June 14CA $384
BOSWashingtonJune 6 to June 7CA $418
LAXWashingtonJune 7 to June 8CA $700
LAXChantillyJune 7 to June 8CA $743
SFOChantillyJune 8 to June 13CA $918
SFOBaltimoreJune 8 to June 13CA $986
SFOWashingtonJune 8 to June 13CA $1,043
*Prices include taxes and fees

Your guide to flights to Winchester, VA

Air Canada, 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 $110 and CA $1,043. 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 $110. 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 June 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 Jun 2 to Jun 3
CA $88
CA $100 total
includes taxes & fees
Jun 2 - Jun 3
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! (1,003 reviews)
"Nice"

Reviewed on May 28, 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 $97 per night from Jun 2 to Jun 3
CA $97
CA $105 total
includes taxes & fees
Jun 2 - Jun 3
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! (1,110 reviews)
"Had an odor like cat pee in hall outside my room. TV was very confusing."

Reviewed on May 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 $110 per night from Jun 2 to Jun 3
CA $110
CA $123 total
includes taxes & fees
Jun 2 - Jun 3
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! (507 reviews)
"Exactly as described. An older mom and pop motel which is deceiving from the outside. The room was updated, VERY CLEAN, and the bathroom was excellent. A great stay on my way home from DC. Would definitely stay again."

Reviewed on Apr. 22, 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 ...
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

Get rates
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 Jun 2 to Jun 3
CA $88
CA $100 total
includes taxes & fees
Jun 2 - Jun 3
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! (1,003 reviews)
"Nice"

Reviewed on May 28, 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 $97 per night from Jun 2 to Jun 3
CA $97
CA $105 total
includes taxes & fees
Jun 2 - Jun 3
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! (1,110 reviews)
"Had an odor like cat pee in hall outside my room. TV was very confusing."

Reviewed on May 30, 2025

Travelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is CA $133 per night from Jun 10 to Jun 11
CA $133
CA $161 total
includes taxes & fees
Jun 10 - Jun 11
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! (381 reviews)
Wayside Inn charming
"Connecting with Family and Friends. Wanted to stay someplace interesting not a box/tel. Wayside was charming and interesting. An old, so expectations should be tailored accordingly."

Reviewed on Apr. 26, 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 ...
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

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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 $134 per night from Jun 2 to Jun 3
CA $134
CA $146 total
includes taxes & fees
Jun 2 - Jun 3
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! (1,001 reviews)
"Friendly staff, comfortable beds TV substandard, no towel racks"

Reviewed on May 21, 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 $175 per night from Jun 15 to Jun 16
CA $175
CA $195 total
includes taxes & fees
Jun 15 - Jun 16
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)
"Loved this hotel. So clean, staff is so friendly, east access. Will definitely stay here on our next trip."

Reviewed on May 27, 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 $116 per night from Jun 9 to Jun 10
CA $116
CA $126 total
includes taxes & fees
Jun 9 - Jun 10
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! (1,001 reviews)
"Excellent breakfast and nice remodeled rooms."

Reviewed on May 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 $157 per night from Jun 22 to Jun 23
CA $157
CA $175 total
includes taxes & fees
Jun 22 - Jun 23
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! (1,002 reviews)
"Nice hotel. The room was well appointed/remodeled. Staff were very friendly and helpful. Good breakfast."

Reviewed on May 23, 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.
Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Don't see what you're looking for?
See all available trips from Toronto to Winchester
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Need a car after flight to Winchester?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

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.

*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.