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
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | February 9 to February 16 | $58 |
| ATL | Baltimore | February 12 to February 16 | $58 |
| FLL | Baltimore | February 5 to February 8 | $59 |
| CLT | Baltimore | February 26 to February 28 | $90 |
| DFW | Baltimore | February 2 to February 4 | $123 |
| FLL | Washington | February 26 to March 2 | $127 |
| ATL | Washington | February 3 to February 4 | $130 |
| DFW | Washington | February 3 to February 7 | $130 |
| BOS | Baltimore | February 10 to February 17 | $139 |
| LAX | Washington | February 24 to March 3 | $148 |
| SFO | Washington | February 11 to March 14 | $149 |
| SFO | Chantilly | March 4 to March 11 | $149 |
| SFO | Baltimore | March 11 to March 17 | $150 |
| BOS | Washington | March 31 to April 4 | $157 |
| CLT | Washington | March 2 to March 4 | $181 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Baltimore | January 17 to January 21 | $87 |
| ATL | Chantilly | January 18 to January 24 | $143 |
| ATL | Baltimore | January 17 to January 24 | $163 |
| CLT | Chantilly | January 17 to January 26 | $186 |
| CLT | Baltimore | January 17 to January 19 | $189 |
| FLL | Chantilly | January 18 to January 24 | $216 |
| DFW | Washington | January 18 to January 24 | $223 |
| DFW | Baltimore | January 17 to January 19 | $224 |
| CLT | Washington | January 18 to January 29 | $254 |
| BOS | Washington | January 18 to January 23 | $260 |
| LAX | Baltimore | January 18 to January 26 | $306 |
| SFO | Washington | January 17 to January 22 | $321 |
| ATL | Washington | January 18 to January 24 | $335 |
| BOS | Baltimore | January 18 to February 16 | $419 |
| SFO | Baltimore | January 18 to January 21 | $521 |
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
$59 nightly
The price is $67 total per night from Jan 31 to Feb 1
$67 total
Jan 31 - Feb 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! (1,002 reviews)
Stayed in winfmg attached to front desk-lobby, which is designed for accessability. Just randomly assigned to me, but will ask for in future as it is fresher feeling than seoarate building with bulk of the room. Very friendly front desk person played with my Frenchie at check-in and departure, making ...
Reviewed on Jan 7, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Jan 13 to Jan 14
$74 total
Jan 13 - Jan 14
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! (1,086 reviews)
C'était propre et tranquille
Reviewed on Jan 11, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$68 nightly
The price is $76 total per night from Jan 13 to Jan 14
$76 total
Jan 13 - Jan 14
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! (544 reviews)
The room was cleaner than expected! No heat in the bathroom and there is a space under the door which lets air in but all in all a cute place. Outdated but the price is reflective of that. Very nice owners. I jad to unplug the fridge to ude the micriwave ans put the coffeepot in bathroom to ise because ...
Reviewed on Dec 29, 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
$59 nightly
The price is $67 total per night from Jan 31 to Feb 1
$67 total
Jan 31 - Feb 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! (1,002 reviews)
Stayed in winfmg attached to front desk-lobby, which is designed for accessability. Just randomly assigned to me, but will ask for in future as it is fresher feeling than seoarate building with bulk of the room. Very friendly front desk person played with my Frenchie at check-in and departure, making ...
Reviewed on Jan 7, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$68 nightly
The price is $74 total per night from Jan 13 to Jan 14
$74 total
Jan 13 - Jan 14
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! (1,086 reviews)
C'était propre et tranquille
Reviewed on Jan 11, 2026
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Jan 13 to Jan 14
$98 total
Jan 13 - Jan 14
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! (409 reviews)
The property, both guest room and public areas, were clean and nicely arranged.
Reviewed on Dec 23, 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
$83 nightly
The price is $91 total per night from Jan 25 to Jan 26
$91 total
Jan 25 - Jan 26
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! (1,002 reviews)
It was all totally smooth
Reviewed on Jan 7, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Jan 18 to Jan 19
$126 total
Jan 18 - Jan 19
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)
We like staying here on our way south.
Reviewed on Jan 1, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Jan 18 to Jan 19
$92 total
Jan 18 - Jan 19
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! (1,001 reviews)
Clean room, front dest service.
Reviewed on Jan 5, 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
$98 nightly
The price is $109 total per night from Jan 18 to Jan 19
$109 total
Jan 18 - Jan 19
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! (1,005 reviews)
Front desk staff very friendly
Reviewed on Dec 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.
Winchester flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Los Angeles to Winchester
View all tripsNeed a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$26
$52 total
found 3 days ago
Compact
Hanover, District of Columbia, USA
$26
$52 total
found 3 days ago
Midsize
Hanover, District of Columbia, USA
$34
$68 total
found 2 days ago
Special
Hanover, District of Columbia, USA
$37
$74 total
found 2 days ago
Lowest prices found within the past 3 days. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Plane Tickets To Winchester
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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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