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 $66 and $29 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | August 11 to August 19 | $66 |
| CLT | Baltimore | August 18 to August 20 | $69 |
| FLL | Baltimore | August 4 to August 11 | $78 |
| ATL | Chantilly | September 1 to September 1 | $93 |
| DFW | Baltimore | August 15 to August 20 | $102 |
| BOS | Washington | September 2 to September 2 | $138 |
| BOS | Baltimore | August 12 to August 19 | $143 |
| ATL | Washington | August 11 to August 18 | $177 |
| DAL | Washington | August 18 to August 19 | $181 |
| BOS | Chantilly | August 1 to August 4 | $189 |
| CLT | Chantilly | July 1 to July 8 | $214 |
| LAX | Baltimore | August 6 to August 10 | $244 |
| LAX | Chantilly | August 14 to August 17 | $251 |
| SFO | Baltimore | August 10 to August 18 | $300 |
| FCO | Baltimore | August 28 to October 6 | $689 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Baltimore | June 13 to June 24 | $220 |
| ATL | Chantilly | June 12 to June 15 | $231 |
| ATL | Baltimore | June 12 to June 14 | $231 |
| MCO | Chantilly | June 12 to June 13 | $270 |
| CLT | Washington | June 13 to June 19 | $386 |
| BOS | Washington | June 12 to June 20 | $391 |
| ATL | Washington | June 14 to June 21 | $398 |
| DFW | Chantilly | June 12 to June 16 | $408 |
| BOS | Baltimore | June 12 to June 15 | $410 |
| BOS | Chantilly | June 12 to June 14 | $411 |
| LAX | Chantilly | June 12 to June 14 | $420 |
| DFW | Washington | June 12 to June 16 | $422 |
| LAX | Washington | June 13 to June 16 | $437 |
| LAX | Baltimore | June 12 to June 15 | $511 |
| FCO | Baltimore | June 12 to June 28 | $1,150 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $66 |
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
$74 nightly
The price is $84 total per night from Jun 12 to Jun 13
$84 total
Jun 12 - Jun 13
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! (1,007 reviews)
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Jun 11 to Jun 12
$77 total
Jun 11 - Jun 12
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! (1,059 reviews)
"Was a nice stop no complaints. It was as expected at a good value"
Reviewed on Jun 7, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$82 nightly
The price is $91 total per night from Jun 30 to Jul 1
$91 total
Jun 30 - Jul 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 ...
8.2/10 Very Good! (556 reviews)
"Clean, quiet, good location."
Reviewed on May 25, 2026
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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 ...
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
$74 nightly
The price is $84 total per night from Jun 12 to Jun 13
$84 total
Jun 12 - Jun 13
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! (1,007 reviews)
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $77 total per night from Jun 11 to Jun 12
$77 total
Jun 11 - Jun 12
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! (1,059 reviews)
"Was a nice stop no complaints. It was as expected at a good value"
Reviewed on Jun 7, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from Jun 14 to Jun 15
$159 total
Jun 14 - Jun 15
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! (437 reviews)
"Clean, well-maintained, delicious food, hot shower!"
Reviewed on Jun 7, 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 6 to Jul 7
$102 total
Jul 6 - Jul 7
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! (1,003 reviews)
"Very disappointed as we have stayed here before but this time was not good. Our floor was terribly dirty, didn't have enough towels, the room looked as if had been partially remodeled but was not finished, and the pool was closed. Not worth the money and we won't be back the next ti.e we are in the ..."
Reviewed on Jun 4, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$113 nightly
The price is $126 total per night from Jun 21 to Jun 22
$126 total
Jun 21 - Jun 22
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! (1,004 reviews)
"Standard hotel. Neither excellent nor lacking."
Reviewed on Jun 7, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$88 nightly
The price is $96 total per night from Jun 21 to Jun 22
$96 total
Jun 21 - Jun 22
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! (1,007 reviews)
"Inside is definitely better than the outside property. Friendly staff, room was clean. Close to shopping and restaurants."
Reviewed on Jun 9, 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
$126 nightly
The price is $141 total per night from Jul 5 to Jul 6
$141 total
Jul 5 - Jul 6
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)
"Excellent swimming pool, a little cool. Room was very spacious and clean."
Reviewed on Jun 9, 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.
Need a Car For After Your Flight?
Economy
Hanover, District of Columbia, USA
$43
$86 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$43
$86 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$46
$92 total
found 1 day ago
Standard
Hanover, District of Columbia, USA
$48
$96 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!
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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