Cheap Flights to Winchester from $30
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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 $60 and $30 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, just found
$60
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | February 2 to February 2 | $63 |
| ATL | Baltimore | February 2 to February 2 | $63 |
| FLL | Baltimore | December 25 to January 1 | $65 |
| DFW | Baltimore | January 25 to February 6 | $68 |
| CLT | Baltimore | January 15 to January 18 | $68 |
| DFW | Chantilly | January 18 to January 18 | $95 |
| FLL | Washington | January 17 to January 18 | $117 |
| ATL | Washington | January 20 to January 24 | $139 |
| BOS | Baltimore | January 23 to January 30 | $139 |
| BOS | Chantilly | January 28 to February 1 | $142 |
| LAX | Washington | January 31 to January 31 | $187 |
| LAX | Baltimore | January 7 to January 30 | $188 |
| DFW | Washington | January 28 to January 31 | $192 |
| LAX | Chantilly | February 26 to March 7 | $192 |
| SFO | Baltimore | December 14 to January 8 | $222 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Baltimore | November 29 to December 13 | $216 |
| ATL | Chantilly | November 29 to December 7 | $221 |
| ATL | Baltimore | November 30 to December 6 | $227 |
| BOS | Chantilly | November 29 to December 3 | $232 |
| CLT | Chantilly | November 30 to December 8 | $338 |
| BOS | Washington | November 30 to December 3 | $345 |
| MCO | Washington | November 29 to December 1 | $391 |
| LAX | Washington | November 29 to December 2 | $397 |
| SFO | Washington | November 29 to December 4 | $433 |
| FLL | Washington | November 29 to December 13 | $459 |
| DFW | Baltimore | November 29 to December 2 | $470 |
| ATL | Washington | November 30 to December 1 | $538 |
| SFO | Chantilly | November 29 to December 14 | $539 |
| BOS | Baltimore | November 30 to December 1 | $630 |
| SFO | Baltimore | November 30 to December 3 | $681 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $60 |
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
$68 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
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! (1,005 reviews)
Great room at a great price. Front desk staff went above and beyond to make it a great stay.
Reviewed on Nov 19, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 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. ...
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.
Reviewed on Nov 23, 2025
Twi-Lite Inn
53 West 14th Street Front Royal VA
$65 nightly
The price is $72 total per night from Nov 30 to Dec 1
$72 total
Nov 30 - Dec 1
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 ...
8/10 Very Good! (537 reviews)
Clean, very cute room! I love how old school it all was. The heat lamp in the bathroom took me back to my childhood. Very happy with my stay.
Reviewed on Nov 19, 2025
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 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
$68 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
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! (1,005 reviews)
Great room at a great price. Front desk staff went above and beyond to make it a great stay.
Reviewed on Nov 19, 2025
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Dec 1 to Dec 2
$74 total
Dec 1 - Dec 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. ...
8.4/10 Very Good! (1,093 reviews)
Clean and comfortable.
Reviewed on Nov 23, 2025
Wayside Inn
7783 Main St Middletown VA
$131 nightly
The price is $144 total per night from Dec 1 to Dec 2
$144 total
Dec 1 - Dec 2
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 Wayside ...
9.2/10 Wonderful! (404 reviews)
heater worked well, room was neat and clean.
Reviewed on Nov 17, 2025
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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 ...
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
$97 nightly
The price is $105 total per night from Dec 17 to Dec 18
$105 total
Dec 17 - Dec 18
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 ...
8.6/10 Excellent! (1,005 reviews)
As long as I don’t experience anything negative then my stay was great
Reviewed on Nov 20, 2025
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$101 nightly
The price is $113 total per night from Dec 7 to Dec 8
$113 total
Dec 7 - Dec 8
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. ...
8.8/10 Excellent! (1,000 reviews)
Everything was wonderful, especially the mattress which appeared new and was very firm but soft on top.
Reviewed on Nov 2, 2025
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$76 nightly
The price is $82 total per night from Dec 7 to Dec 8
$82 total
Dec 7 - Dec 8
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 ...
9.2/10 Wonderful! (1,003 reviews)
Great room, even better staff! I enjoyed the breakfast as well. Can’t wait to come back!!
Reviewed on Nov 19, 2025
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$99 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
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! (1,002 reviews)
Very clean room , the staff was very friendly and a good breakfast.
Reviewed on Nov 15, 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.
Need a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$29
$58 total
found 2 days ago
Compact
Hanover, District of Columbia, USA
$29
$58 total
found 2 days ago
Midsize
Hanover, District of Columbia, USA
$37
$74 total
found 2 days ago
Special
Hanover, District of Columbia, USA
$45
$90 total
found 1 day ago
Lowest prices found within the past 2 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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