Cheap Flights to Winchester from $32
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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 $68 and $32 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| BOS | Baltimore | August 2 to August 5 | $72 |
| MCO | Chantilly | September 28 to September 28 | $83 |
| ATL | Chantilly | September 23 to September 24 | $88 |
| MCO | Baltimore | July 16 to July 21 | $91 |
| DFW | Baltimore | August 5 to August 9 | $93 |
| MIA | Chantilly | August 25 to August 25 | $108 |
| DFW | Chantilly | September 27 to September 27 | $109 |
| MCO | Washington | September 10 to September 10 | $122 |
| BOS | Washington | September 29 to September 29 | $132 |
| DFW | Washington | September 20 to September 20 | $134 |
| BOS | Chantilly | September 9 to September 16 | $137 |
| MIA | Washington | August 25 to August 27 | $157 |
| SFO | Washington | September 9 to September 10 | $233 |
| FCO | Chantilly | August 27 to September 9 | $442 |
| FCO | Washington | October 3 to October 19 | $652 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| TPA | Baltimore | July 12 to July 21 | $112 |
| ATL | Baltimore | July 12 to July 16 | $112 |
| ATL | Chantilly | July 12 to July 19 | $112 |
| MIA | Chantilly | July 11 to July 13 | $115 |
| TPA | Chantilly | July 12 to July 14 | $147 |
| MCO | Baltimore | July 11 to July 13 | $177 |
| DEN | Washington | July 12 to July 15 | $208 |
| MCO | Chantilly | July 12 to July 13 | $216 |
| LAX | Baltimore | July 12 to July 22 | $261 |
| DEN | Chantilly | July 12 to July 22 | $315 |
| LAX | Washington | July 12 to July 21 | $322 |
| ATL | Washington | July 13 to July 15 | $337 |
| EKW | Washington | July 12 to October 6 | $372 |
| SFO | Washington | July 11 to July 14 | $572 |
| FCO | Baltimore | July 13 to April 28 | $731 |
Winchester DCA Flight Information
Traveling to | Winchester DCA |
|---|---|
Lowest Price | $68 |
Number of Airlines Serving | 3 |
Airlines Serving | Spirit Airlines |
Number of Daily Flights | 5 |
Airlines with Direct Flights | American Airlines, Alaska Airlines, Southwest Airlines |
Find The Perfect Hotel For After Your Flight
Amazing Winchester Accommodation Deals
Motel 6 Winchester, VA
2951 Valley Avenue, Winchester, VA
$64 nightly
The price is $73 total per night from Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
Total includes taxes and fees
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! (1,001 reviews)
"Great for an overnight stay. Clean room. Needs comfortable chairs."
Reviewed on Jul 2, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
$69 nightly
The price is $75 total per night from Jul 9 to Jul 10
$75 total
Jul 9 - Jul 10
Total includes taxes and fees
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. ...
8.4/10 Very Good! (1,103 reviews)
"Hotel was clean, rooms were comfortable bed was also comfy."
Reviewed on Jul 4, 2025
Twi-Lite Inn
53 West 14th Street, Front Royal, VA
$78 nightly
The price is $87 total per night from Jul 28 to Jul 29
$87 total
Jul 28 - Jul 29
Total includes taxes and fees
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! (510 reviews)
"This is such a delightful Inn run by lovely people. Is it a 5 star hotel? No. Was it built in the 70s? Probably. Nonetheless, the pool is crystal clear. The landscaping is gorgeous (The gentleman does it all himself!) Its close to a beautiful state park. The owners couldnt be more friendly. I've ..."
Reviewed on Jun 22, 2025
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Royal Inn Motel
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
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
2951 Valley Avenue, Winchester, VA
$64 nightly
The price is $73 total per night from Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
Total includes taxes and fees
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! (1,001 reviews)
"Great for an overnight stay. Clean room. Needs comfortable chairs."
Reviewed on Jul 2, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
$69 nightly
The price is $75 total per night from Jul 9 to Jul 10
$75 total
Jul 9 - Jul 10
Total includes taxes and fees
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. ...
8.4/10 Very Good! (1,103 reviews)
"Hotel was clean, rooms were comfortable bed was also comfy."
Reviewed on Jul 4, 2025
Wayside Inn
7783 Main St, Middletown, VA
$107 nightly
The price is $118 total per night from Jul 8 to Jul 9
$118 total
Jul 8 - Jul 9
Total includes taxes and fees
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! (389 reviews)
"Old Inn with unique features great for those who don’t want the cookie cutter experience. Great history and furniture was amazing, the building itself was incredible. Lot of history in the building. The manager was very knowledgeable about the history and property. Staff was great. Enjoyed my ..."
Reviewed on Jun 30, 2025
Save an average of 15% on thousands of hotels when you're signed in
Hotel Strasburg
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 Museum and Hupp's Hill Civil ...
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
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
141 Kernstown Commons Blvd, Winchester, VA
$99 nightly
The price is $108 total per night from Jul 8 to Jul 9
$108 total
Jul 8 - Jul 9
Total includes taxes and fees
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)
Nice stay!
"Nice stay. Everything was clean and comfortable. Breakfast was good. Friendly staff. Would definitely stay here again."
Reviewed on Jul 2, 2025
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike, Strasburg, VA
$118 nightly
The price is $131 total per night from Jul 20 to Jul 21
$131 total
Jul 20 - Jul 21
Total includes taxes and fees
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! (1,001 reviews)
"Fast frinedly service po warm and clean"
Reviewed on Jun 20, 2025
Quality Inn
1601 Martinsburg Pike, Winchester, VA
$93 nightly
The price is $101 total per night from Jul 13 to Jul 14
$101 total
Jul 13 - Jul 14
Total includes taxes and fees
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)
"Very clean, very kind people at check-in. Everyone was working and busy doing something. Even had recycling containers but food was in one of them."
Reviewed on Jul 3, 2025
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Hampton Inn Front Royal
9800 Winchester Rd, Front Royal, VA
$111 nightly
The price is $123 total per night from Aug 3 to Aug 4
$123 total
Aug 3 - Aug 4
Total includes taxes and fees
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! (1,008 reviews)
"My experience was great, the only thing that bother me was the noise of the AC at night Atleast my room 209 was a bit loudly on that. And the shower i could tell the cleaning crew only wipes down the showers instead of scrubbing it. Staff and everything else was great."
Reviewed on Jun 29, 2025
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.
Winchester flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Economy
Arlington, Virginia, USA
$35
$94 total
found 1 day ago
Special
Arlington, Virginia, USA
$35
$94 total
found 1 day ago
Standard
Arlington, District of Columbia, USA
$35
$95 total
found 1 day ago
Compact
Arlington, Virginia, USA
$35
$94 total
found 1 day ago
Frequently asked questions
Plane Tickets To Winchester
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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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Winchester Hotels
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Winchester Vacation Rentals
Great Deals on alternative accommodations
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