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 $46 and $24 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.
IAD
Washington Dulles Intl.
$47 Roundtrip, found 2 hours ago
$47
Roundtrip
found 2 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | October 20 to October 24 | $46 |
| ATL | Baltimore | December 8 to December 10 | $90 |
| ATL | Washington | December 9 to December 16 | $127 |
| CLT | Baltimore | October 12 to October 15 | $154 |
| BOS | Baltimore | October 26 to October 26 | $168 |
| BOS | Chantilly | December 1 to December 5 | $171 |
| BOS | Washington | November 18 to December 12 | $171 |
| DFW | Washington | October 20 to October 28 | $201 |
| CLT | Washington | October 20 to October 21 | $212 |
| SFO | Chantilly | October 24 to October 28 | $233 |
| LAX | Chantilly | October 8 to October 13 | $249 |
| LAX | Baltimore | November 4 to November 8 | $255 |
| LAX | Washington | October 28 to November 1 | $262 |
| SFO | Washington | October 19 to October 21 | $267 |
| FCO | Baltimore | November 9 to November 13 | $606 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | September 19 to September 29 | $201 |
| ATL | Chantilly | September 19 to September 20 | $270 |
| ATL | Baltimore | September 19 to September 20 | $270 |
| FLL | Baltimore | September 19 to September 20 | $338 |
| CLT | Chantilly | September 19 to September 20 | $354 |
| FLL | Washington | September 19 to September 23 | $382 |
| ATL | Washington | September 19 to September 20 | $457 |
| SFO | Baltimore | September 20 to October 7 | $458 |
| DFW | Washington | September 19 to September 23 | $484 |
| SFO | Chantilly | September 20 to September 26 | $492 |
| LAX | Baltimore | September 20 to September 23 | $494 |
| BOS | Washington | September 20 to September 22 | $501 |
| CLT | Washington | September 19 to September 20 | $503 |
| LAX | Washington | September 19 to September 25 | $524 |
| FCO | Chantilly | September 20 to September 29 | $1,046 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $46 |
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
$72 nightly
The price is $82 total per night from Sep 30 to Oct 1
$82 total
Sep 30 - Oct 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. ...
8.2/10 Very Good! (1,000 reviews)
"Okay stay with comfortable beds. You must keep in mind the low cost. Room very minimal but nice clean hard floors so no mystery carpet. Overall we got our money's worth."
Reviewed on Sep 17, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 20 to Sep 21
$76 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,074 reviews)
"Better breakfast"
Reviewed on Sep 17, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Sep 20 to Sep 21
$91 total
Sep 20 - Sep 21
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! (579 reviews)
"Very clean and comfortable room!"
Reviewed on Sep 14, 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 Blue Ridge Arts Council and Gallery and Front ...
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
$72 nightly
The price is $82 total per night from Sep 30 to Oct 1
$82 total
Sep 30 - Oct 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. ...
8.2/10 Very Good! (1,000 reviews)
"Okay stay with comfortable beds. You must keep in mind the low cost. Room very minimal but nice clean hard floors so no mystery carpet. Overall we got our money's worth."
Reviewed on Sep 17, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$69 nightly
The price is $76 total per night from Sep 20 to Sep 21
$76 total
Sep 20 - Sep 21
Total with taxes and fees
Stay at this motel in Winchester. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,074 reviews)
"Better breakfast"
Reviewed on Sep 17, 2026
Wayside Inn
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 15 to Oct 16
$104 total
Oct 15 - Oct 16
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! (447 reviews)
"This is a quaint, historical place to stay with lots of antiques and interesting furnishings. We enjoyed the patio, pub and live music on the night we stayed. We would stay again if we find ourselves in the area."
Reviewed on Sep 17, 2026
Save an average of 15% on thousands of hotels when you're signed in
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
$100 nightly
The price is $111 total per night from Oct 11 to Oct 12
$111 total
Oct 11 - Oct 12
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! (1,000 reviews)
"The room was very clean. The bed was comfortable. The bathroom was immaculate and it was a great breakfast. I enjoyed my stay thank you very much."
Reviewed on Sep 15, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$118 nightly
The price is $131 total per night from Sep 28 to Sep 29
$131 total
Sep 28 - Sep 29
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)
"Front desk staff - AWESOME! I needed to speak with someone the day before arrival, and the staff was awesome! Very helpful! On arrival, the same staff member was cordial, friendly, and very efficient! The room was spacious and well equipped, but felt old. It's in need of some updating. The mattress ..."
Reviewed on Sep 13, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $94 total per night from Sep 24 to Sep 25
$94 total
Sep 24 - Sep 25
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! (1,002 reviews)
"The hotel is conveniently located, clean, pleasant and very reasonably priced. It was just what we needed for an overnight stop with a dog."
Reviewed on Sep 16, 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
$120 nightly
The price is $133 total per night from Sep 29 to Sep 30
$133 total
Sep 29 - Sep 30
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 ...
9.2/10 Wonderful! (1,003 reviews)
"The property was excellent only thing was the pool wasn’t working. We were willing to pay the price per night because we thought we would be able to swim. Breakfast was awesome lots of good food and always plenty."
Reviewed on Sep 17, 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 - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Standard SUV
Baltimore, Maryland, USA
$45
$132 total
found 2 days ago
Mini Van
Baltimore, Maryland, USA
$47
$138 total
found 2 days ago
Compact SUV
BALTIMORE, USA
$54
$155 total
found 3 days ago
Economy
Hanover, USA
$54
$160 total
found 2 days 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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