Cheap Flights to Winchester from $29
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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 $58 and $29 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
$58 Roundtrip, found 11 hours ago
$58
Roundtrip
found 11 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | September 1 to September 8 | $58 |
| FLL | Chantilly | August 20 to August 25 | $88 |
| CLT | Baltimore | July 29 to July 29 | $95 |
| FLL | Baltimore | August 12 to August 19 | $111 |
| BOS | Baltimore | August 25 to August 29 | $117 |
| BOS | Washington | August 25 to August 29 | $117 |
| ATL | Washington | September 8 to September 12 | $169 |
| CLT | Chantilly | July 22 to July 29 | $185 |
| FLL | Washington | July 28 to July 28 | $196 |
| DFW | Washington | September 15 to September 16 | $210 |
| LAX | Washington | September 9 to September 15 | $227 |
| LAX | Baltimore | August 18 to August 25 | $248 |
| SFO | Washington | August 1 to August 8 | $252 |
| SFO | Baltimore | September 1 to September 9 | $252 |
| SFO | Chantilly | October 6 to October 13 | $354 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | July 4 to July 5 | $183 |
| CLT | Baltimore | July 4 to July 7 | $191 |
| ATL | Chantilly | July 4 to July 5 | $233 |
| FLL | Washington | July 4 to July 8 | $279 |
| ATL | Washington | July 5 to July 7 | $281 |
| FLL | Baltimore | July 5 to July 11 | $324 |
| CLT | Chantilly | July 4 to July 24 | $335 |
| LAX | Chantilly | July 4 to July 16 | $357 |
| LAX | Washington | July 4 to July 16 | $396 |
| DFW | Baltimore | July 5 to July 7 | $434 |
| LAX | Baltimore | July 4 to July 13 | $486 |
| SFO | Washington | July 5 to July 17 | $611 |
| SFO | Baltimore | July 4 to July 8 | $657 |
| FCO | Chantilly | July 4 to July 18 | $774 |
| SFO | Chantilly | July 5 to July 9 | $838 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Winchester Accommodation Deals
Motel 6 Winchester, VA
2951 Valley Avenue Winchester VA
$67 nightly
The price is $75 total per night from Aug 1 to Aug 2
$75 total
Aug 1 - Aug 2
Total with 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! (1,004 reviews)
"Was a solo traveler and booked last minute. Reviews were overall good. The motel was clean and comfortable. A great value for the price and recommend."
Reviewed on Jul 1, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Jul 2 to Jul 3
$76 total
Jul 2 - Jul 3
Total with 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. ...
8.6/10 Excellent! (1,052 reviews)
"A"
Reviewed on Jul 1, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$78 nightly
The price is $87 total per night from Jul 27 to Jul 28
$87 total
Jul 27 - Jul 28
Total with 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 ...
8.2/10 Very Good! (563 reviews)
"We were in town for a wedding for a couple of nights & just wanted a place to sleep that wasn't crazy expensive....The room was clean, but small and outdated. The stay was overall quiet. The room had a fridge and cold AC which was appreciated. We didn't use the pool but it looked clean and well kept. ..."
Reviewed on Jun 28, 2026
Save an average of 15% on thousands of hotels when you're signed in
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 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
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
$67 nightly
The price is $75 total per night from Aug 1 to Aug 2
$75 total
Aug 1 - Aug 2
Total with 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! (1,004 reviews)
"Was a solo traveler and booked last minute. Reviews were overall good. The motel was clean and comfortable. A great value for the price and recommend."
Reviewed on Jul 1, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Jul 2 to Jul 3
$76 total
Jul 2 - Jul 3
Total with 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. ...
8.6/10 Excellent! (1,052 reviews)
"A"
Reviewed on Jul 1, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Jul 5 to Jul 6
$159 total
Jul 5 - Jul 6
Total with 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 Cedar ...
9.2/10 Wonderful! (440 reviews)
"Quaint and quiet. Love historic places like this."
Reviewed on Jun 30, 2026
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Hotel Strasburg
213 S. Holliday Street Strasburg VA
Book a stay at this historic hotel in Strasburg. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Strasburg Museum and Hupp's Hill Civil ...
7.8/10 Good! (731 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
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
$94 nightly
The price is $102 total per night from Jul 26 to Jul 27
$102 total
Jul 26 - Jul 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,001 reviews)
"The bed was comfortable and cozy and the breakfast was good. Staff people were very nice. The reason for knocking off a star is that the room smelled kind of like stale cigarettes and the carpet in the room had stains. However it was “good enough” for an overnight while traveling and I have a pretty ..."
Reviewed on Jul 1, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$105 nightly
The price is $117 total per night from Jul 12 to Jul 13
$117 total
Jul 12 - Jul 13
Total with 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. ...
9/10 Wonderful! (1,000 reviews)
"The staff was exceptionally helpful and friendly. Everything was clean. The breakfast was well-maintained with fresh food items. We were very pleased with our stay."
Reviewed on Jun 30, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$93 nightly
The price is $103 total per night from Jul 12 to Jul 13
$103 total
Jul 12 - Jul 13
Total with 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 ...
9.4/10 Exceptional! (1,001 reviews)
"The water came out of the spigot very yellow."
Reviewed on Jul 1, 2026
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$130 nightly
The price is $145 total per night from Jul 8 to Jul 9
$145 total
Jul 8 - Jul 9
Total with 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 ...
9/10 Wonderful! (1,001 reviews)
"Room was clean and comfy. Front desk was very nice and helpful. Breakfast was good"
Reviewed on Jun 27, 2026
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.
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See all available trips from Minneapolis to Winchester
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View all tripsNeed a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$38
$76 total
found 5 days ago
Compact
Hanover, District of Columbia, USA
$38
$76 total
found 5 days ago
Midsize
Hanover, District of Columbia, USA
$42
$84 total
found 5 days ago
Special
Hanover, District of Columbia, USA
$45
$90 total
found 5 days ago
Lowest prices found within the past 5 days. Prices and availability subject to change. Additional terms may apply.
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!
More Ways To Wander
Winchester Hotels
Find the perfect hotel after your flight
Winchester Vacation Rentals
Great Deals on alternative accommodations
Winchester Car Rentals
Affordable cars to get you around town
Winchester Vacations
Save more by combining flights, hotels and cars
Things to do in Winchester
Activities, attractions and tours
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