Cheap Flights to Winchester from $24

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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 $97 and $24 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
CMHWashingtonMay 11 to May 15$136
CMHBaltimoreMay 11 to May 15$152
CMHChantillyMay 22 to May 26$165
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CMHWashingtonApril 20 to May 7$318
CMHChantillyApril 21 to April 22$396
CMHBaltimoreApril 20 to April 27$406
*Prices include taxes and fees

Winchester DCA Flight Information

Traveling to
Winchester DCA
Lowest Price
$97
Number of Airlines Serving
3
Airlines Serving
Frontier Airlines, Spirit Airlines, American Airlines
Number of Daily Flights
6
Airlines with Direct Flights
American Airlines, Alaska Airlines, Southwest Airlines

Winchester Flight Schedule

CarrierFlightDepart CMHArrive DCAWed
4/17
Thu
4/18
Fri
4/19
Sat
4/20
Sun
4/21
Mon
4/22
Tue
4/23
Stops
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0 Stops
AA470000:32 pm01:55 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
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AA474103:36 pm04:59 pmCheck FareCheck FareCheck Fare
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AA373905:35 pm06:54 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops

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 $62 per night from Apr 21 to Apr 22
$62
per night
Apr 21 - Apr 22
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! (1,000 reviews)
"Clean, safe, Spartan, and perfect!"

Reviewed on Apr 4, 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 $72 per night from Apr 25 to Apr 26
$72
per night
Apr 25 - Apr 26
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 rooms ...
7.8/10 Good! (1,057 reviews)
"Lots of room, cheap and comfortable."

Reviewed on Apr 14, 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 Apr 17 to Apr 18
$75
per night
Apr 17 - Apr 18
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! (446 reviews)
"This hotel is pretty good for the price! Clean and quiet!"

Reviewed on Apr 9, 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.

Luxury Hotels in Winchester

Motel 6 Winchester, VA

Motel 6 Winchester, VA

2 out of 5
2951 Valley Avenue, Winchester, VA
The price is $62 per night from Apr 21 to Apr 22
$62
per night
Apr 21 - Apr 22
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! (1,000 reviews)
"Clean, safe, Spartan, and perfect!"

Reviewed on Apr 4, 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 $72 per night from Apr 25 to Apr 26
$72
per night
Apr 25 - Apr 26
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 rooms ...
7.8/10 Good! (1,057 reviews)
"Lots of room, cheap and comfortable."

Reviewed on Apr 14, 2024

Travelodge by Wyndham Winchester
Wayside Inn

Wayside Inn

3.5 out of 5
7783 Main St, Middletown, VA
The price is $105 per night from Apr 21 to Apr 22
$105
per night
Apr 21 - Apr 22
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and a terrace. Popular attractions Wayside Theater and Cedar Creek and Belle Grove National ...
9.2/10 Wonderful! (326 reviews)
Charming and delightful
"Lovely stay. Felt like i was at my great grandmothers house."

Reviewed on Apr 11, 2024

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 Strasburg Theater and Strasburg Town ...
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
Great for families

Country Inn & Suites by Radisson, Winchester, VA

3 out of 5
141 Kernstown Commons Blvd, Winchester, VA
The price is $85 per night from May 12 to May 13
$85
per night
May 12 - May 13
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)

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

Travelers say...
"The management and staff try very hard to accommodate their guest with concern, understanding, and kindness."

Reviewed on Apr 14, 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 $118 per night from Apr 24 to Apr 25
$118
per night
Apr 24 - Apr 25
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 rooms ...
8.8/10 Excellent! (994 reviews)

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

Travelers say...
"Clean and easy"

Reviewed on Apr 13, 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 $75 per night from May 12 to May 13
$75
per night
May 12 - May 13
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! (969 reviews)

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

Travelers say...
"Affordable and quiet. Close to the new job."

Reviewed on Mar 22, 2024

Quality Inn
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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 Apr 28 to Apr 29
$110
per night
Apr 28 - Apr 29
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 staff ...
8.8/10 Excellent! (1,001 reviews)

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

Travelers say...
"Leslie was extremely helpful and kind! Loved everything about the room, great job!!"

Reviewed on Apr 12, 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

The Royal Sonesta Washington DC Dupont Circle
YOTEL Washington DC
The Graham Georgetown
Don't see what you're looking for?
See all available trips from CMH-All Airports to Winchester
View all trips
Prices and availability subject to change. Additional terms may apply.

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.