Cheap Flights to Winchester from $21

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How Much Does it Cost To Fly To Winchester?

The cheapest prices found with in the last 7 days for return flights were $41 and $21 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
MIABaltimoreJune 5 to June 11$41
DFWBaltimoreAugust 14 to August 27$93
MCOWashingtonJune 10 to June 11$107
LAXBaltimoreAugust 17 to August 28$126
DENBaltimoreJune 11 to June 25$128
BOSWashingtonAugust 18 to August 18$133
BOSChantillyJune 21 to June 24$139
DENWashingtonAugust 17 to August 24$140
TPAChantillyAugust 9 to August 11$142
ATLChantillyJuly 17 to July 23$169
ATLWashingtonAugust 6 to August 21$169
DFWChantillyAugust 31 to September 10$208
SFOBaltimoreAugust 20 to August 31$210
FCOWashingtonJuly 15 to July 22$556
FCOChantillyJune 8 to June 16$556
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ATLBaltimoreMay 31 to June 4$147
BOSChantillyJune 2 to June 5$179
LAXBaltimoreJune 2 to June 9$204
MIAWashingtonMay 31 to June 2$214
BOSWashingtonJune 1 to June 18$219
MCOChantillyJune 2 to June 6$237
DENBaltimoreJune 1 to June 6$258
MIAChantillyMay 31 to June 2$298
DFWChantillyJune 1 to August 3$341
DENWashingtonJune 2 to June 4$401
ATLChantillyJune 2 to June 17$421
DENChantillyJune 1 to June 6$427
SFOChantillyMay 31 to October 8$430
LAXChantillyJune 1 to June 12$459
FCOWashingtonJune 2 to June 10$603
*Prices include taxes and fees

Winchester DCA Flight Information

Traveling to
Winchester DCA
Lowest Price
$41
Number of Airlines Serving
4
Airlines Serving
Spirit Airlines
Number of Daily Flights
7
Airlines with Direct Flights
American Airlines, Alaska Airlines, Southwest Airlines, United Airlines

Find The Perfect Hotel For After Your Flight

Amazing Winchester Accommodation Deals

Motel 6 Winchester, VA

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is $66 per night from Jun 5 to Jun 6
$66
per night
Jun 5 - Jun 6
Stay at this motel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
8/10 Very Good! (1,002 reviews)
"Very friendly staff, easy check in, close to gas stations, dining, and grocery stores"

Reviewed on May 25, 2024

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 $70 per night from Jun 9 to Jun 10
$70
per night
Jun 9 - Jun 10
Book a stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (1,068 reviews)
"The room was very good. The breakfast was mediocre."

Reviewed on May 25, 2024

Travelodge by Wyndham Winchester
Twi-Lite Inn

Twi-Lite Inn

2 out of 5
53 West 14th Street, Front Royal, VA
The price is $75 per night from May 29 to May 30
$75
per night
May 29 - May 30
Stay at this motel in Front Royal. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions ...
8/10 Very Good! (453 reviews)
"Staying at the Twi-Lite was like being in a time capsule in the best way. Our room was super clean, the beds were great, and we appreciated the convenience of the microwave and refrigerator in our room. Loved the retro feel of this mid century property. The pool looked pristine, although the weather ..."

Reviewed on May 21, 2024

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 Front Royal Entrance Shenandoah National Park ...
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.

Family Friendly Hotels in Winchester

Country Inn & Suites by Radisson, Winchester, VA
Great for families

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
The price is $106 per night from Jun 2 to Jun 3
$106
per night
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! (1,004 reviews)

Families like: Indoor pools, extra beds/cribs, free breakfast for the whole family, laundry

A good stay
"I love the country Inn and suites have always chosen this place no matter the location. This location was very clean and the staff was very accommodating. The bed wasn’t the most comfortable, but it was a good stay."

Reviewed on May 27, 2024

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

Fairfield Inn & Suites Strasburg Shenandoah Valley

2.5 out of 5
33760 Old Valley Pike, Strasburg, VA
The price is $123 per night from Jun 2 to Jun 3
$123
per night
Jun 2 - Jun 3
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,000 reviews)

Families like: Indoor pools, free breakfast for the whole family, laundry

Travelers say...
"Very friendly staff and free breakfast"

Reviewed on Apr 22, 2024

Fairfield Inn & Suites Strasburg Shenandoah Valley
Quality Inn
Great for families

Quality Inn

2.5 out of 5
1601 Martinsburg Pike, Winchester, VA
The price is $93 per night from Jun 2 to Jun 3
$93
per night
Jun 2 - Jun 3
Stay at this hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.8/10 Excellent! (1,000 reviews)

Families like: Outdoor pool, extra beds/cribs, free breakfast for the whole family, laundry

Travelers say...
"Easy to find. Pleasant staff. Nice clean room"

Reviewed on May 25, 2024

Quality Inn
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Front Royal
Great for families

Hampton Inn Front Royal

2.5 out of 5
9800 Winchester Rd, Front Royal, VA
The price is $110 per night from Jun 2 to Jun 3
$110
per night
Jun 2 - Jun 3
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)

Families like: Pool, free breakfast for the whole family, laundry

Would stay again!
"Well kept, friendly stay. The bed was a bit more firm than I care for but this is a clean, well run hotel where guests are comfortable hanging out in the well appointed lobby/dining area. Coffee, tea & hot chocolate always available."

Reviewed on May 22, 2024

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.
The Graham Georgetown
Hamilton Hotel Washington DC
Glover Park - Georgetown
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Need a Car For After Your Flight?

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
Whether you’re looking to splurge, or simply grab the necessities, you’ll be treated to some fine retail therapy at Apple Blossom Mall. Want some more options? If you’re looking to stay on top of your health while on vacation, why not get physical at Jim Barnett Park? This popular recreation area will get you out of the gym and into the open air. But there’s more. Shenandoah Valley Discovery Museum has plenty of hands-on activities for active discovery. Your youngsters will be entertained for ages!
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.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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.