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.
IAD
Washington Dulles Intl.
$58 Roundtrip, found 3 hours ago
$58
Roundtrip
found 3 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Baltimore | July 1 to July 7 | $67 |
| CLT | Baltimore | June 9 to June 10 | $70 |
| FLL | Chantilly | July 22 to July 29 | $76 |
| BOS | Washington | August 11 to August 11 | $132 |
| DFW | Chantilly | August 18 to August 25 | $160 |
| DFW | Baltimore | August 11 to August 18 | $166 |
| LAX | Baltimore | July 8 to July 24 | $172 |
| BOS | Baltimore | August 5 to August 6 | $174 |
| ATL | Washington | July 20 to July 22 | $189 |
| CLT | Chantilly | June 16 to June 23 | $190 |
| FLL | Washington | June 4 to June 6 | $200 |
| LAX | Washington | August 14 to August 17 | $213 |
| DFW | Washington | August 24 to September 1 | $214 |
| CLT | Washington | July 16 to July 21 | $235 |
| LAX | Chantilly | June 25 to July 4 | $244 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| CLT | Baltimore | May 24 to May 24 | $136 |
| FLL | Baltimore | May 22 to May 30 | $165 |
| FLL | Chantilly | May 23 to May 27 | $175 |
| FLL | Washington | May 24 to June 1 | $236 |
| MCO | Baltimore | May 23 to May 26 | $311 |
| DFW | Washington | May 24 to May 27 | $346 |
| LAX | Washington | May 23 to May 27 | $370 |
| BOS | Baltimore | May 23 to May 26 | $398 |
| LAX | Chantilly | May 23 to May 26 | $404 |
| LAX | Baltimore | May 24 to May 27 | $405 |
| ATL | Washington | May 23 to May 25 | $419 |
| SFO | Baltimore | May 22 to May 26 | $452 |
| SFO | Washington | May 22 to May 24 | $577 |
| FCO | Chantilly | May 24 to June 9 | $712 |
| FCO | Baltimore | May 24 to June 9 | $2,779 |
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
$72 nightly
The price is $82 total per night from May 24 to May 25
$82 total
May 24 - May 25
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! (1,003 reviews)
"Very nice no complaints."
Reviewed on May 15, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$74 nightly
The price is $81 total per night from May 25 to May 26
$81 total
May 25 - May 26
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! (1,076 reviews)
"Very nice convenient and friendly. Highly recommend"
Reviewed on May 19, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$84 nightly
The price is $93 total per night from May 21 to May 22
$93 total
May 21 - May 22
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! (553 reviews)
"The room was very clean and comfortable. We enjoyed our stay and enjoyed being able to pull up to the room and unload with no steps or elevator to get on."
Reviewed on May 12, 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 May 24 to May 25
$82 total
May 24 - May 25
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! (1,003 reviews)
"Very nice no complaints."
Reviewed on May 15, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$74 nightly
The price is $81 total per night from May 25 to May 26
$81 total
May 25 - May 26
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! (1,076 reviews)
"Very nice convenient and friendly. Highly recommend"
Reviewed on May 19, 2026
Wayside Inn
7783 Main St Middletown VA
$144 nightly
The price is $159 total per night from May 24 to May 25
$159 total
May 24 - May 25
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! (433 reviews)
"was nice and my gf enjoyed it"
Reviewed on May 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
$94 nightly
The price is $102 total per night from Jun 9 to Jun 10
$102 total
Jun 9 - Jun 10
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)
"We stayed 4 nights and received NO room cleaning services, yet were promised 3rd day room would be cleaned and new towels. Terrible TV service too, without a channel guide. Room was roomy and bathroom was nice"
Reviewed on May 18, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$101 nightly
The price is $113 total per night from May 31 to Jun 1
$113 total
May 31 - Jun 1
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)
"It was a nice hotel for an over night stay. The room took a while to cool down but the overall stay was great."
Reviewed on May 18, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from May 26 to May 27
$92 total
May 26 - May 27
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)
"Great."
Reviewed on May 20, 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
$122 nightly
The price is $136 total per night from May 31 to Jun 1
$136 total
May 31 - Jun 1
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! (1,014 reviews)
"Everything was lovely"
Reviewed on May 14, 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.
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?
Economy
Hanover, District of Columbia, USA
$34
$68 total
found 1 day ago
Compact
Hanover, District of Columbia, USA
$34
$68 total
found 1 day ago
Midsize
Hanover, District of Columbia, USA
$38
$76 total
found 1 day ago
Special
Hanover, District of Columbia, USA
$41
$82 total
found 1 day ago
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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