Cheap Flights to Winchester from $28
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
Feel at ease with free flight cancellations within 24 hours of booking
Change your flight without a fee on select flights
How Much Does it Cost To Fly To Winchester?
The cheapest prices found with in the last 7 days for return flights were $56 and $28 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.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 5 hours ago
$56
Roundtrip
found 5 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | April 29 to May 4 | $56 |
| ATL | Baltimore | May 5 to May 9 | $56 |
| FLL | Baltimore | April 25 to April 27 | $56 |
| DFW | Baltimore | April 22 to May 2 | $88 |
| CLT | Baltimore | May 9 to May 16 | $98 |
| BOS | Baltimore | May 5 to May 12 | $108 |
| FLL | Washington | April 30 to May 4 | $113 |
| FLL | Chantilly | April 14 to April 20 | $121 |
| LAX | Baltimore | April 27 to May 5 | $144 |
| SFO | Washington | April 14 to April 18 | $145 |
| BOS | Washington | April 29 to May 5 | $147 |
| BOS | Chantilly | May 12 to May 19 | $148 |
| CLT | Chantilly | May 8 to May 10 | $160 |
| LAX | Chantilly | April 28 to May 5 | $200 |
| FCO | Baltimore | April 7 to April 11 | $590 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | March 7 to March 10 | $121 |
| ATL | Baltimore | March 7 to March 8 | $160 |
| FLL | Baltimore | March 7 to March 8 | $202 |
| BOS | Washington | March 8 to March 10 | $251 |
| BOS | Chantilly | March 8 to March 10 | $251 |
| DFW | Baltimore | March 7 to March 9 | $257 |
| FLL | Chantilly | March 7 to March 8 | $260 |
| DFW | Chantilly | March 8 to March 13 | $291 |
| ATL | Washington | March 7 to March 10 | $333 |
| SFO | Baltimore | March 7 to March 11 | $361 |
| LAX | Washington | March 7 to March 14 | $409 |
| LAX | Chantilly | March 7 to March 16 | $430 |
| LAX | Baltimore | March 6 to March 9 | $471 |
| BOS | Baltimore | March 6 to March 8 | $516 |
| SFO | Washington | March 6 to March 9 | $579 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $56 |
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 Mar 2 to Mar 3
$77 total
Mar 2 - Mar 3
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)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Mar 1 to Mar 2
$76 total
Mar 1 - Mar 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. ...
8.6/10 Excellent! (1,076 reviews)
Room was spacious, bed was comfortable and lots of TV channels. Gentleman that checked us in and out was very courteous.
Reviewed on Feb 24, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$65 nightly
The price is $72 total per night from Mar 1 to Mar 2
$72 total
Mar 1 - Mar 2
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 ...
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
$68 nightly
The price is $77 total per night from Mar 2 to Mar 3
$77 total
Mar 2 - Mar 3
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)
Room clean and staff was nice
Reviewed on Feb 25, 2026
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$70 nightly
The price is $76 total per night from Mar 1 to Mar 2
$76 total
Mar 1 - Mar 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. ...
8.6/10 Excellent! (1,076 reviews)
Room was spacious, bed was comfortable and lots of TV channels. Gentleman that checked us in and out was very courteous.
Reviewed on Feb 24, 2026
Wayside Inn
7783 Main St Middletown VA
$89 nightly
The price is $98 total per night from Mar 1 to Mar 2
$98 total
Mar 1 - Mar 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! (424 reviews)
Interesting unique place. We explored the different rooms, will definitely be back. With ghost hunting equipment.
Reviewed on Feb 26, 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
$91 nightly
The price is $99 total per night from Mar 8 to Mar 9
$99 total
Mar 8 - Mar 9
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)
Very courteous staff - clean hotel, great breakfast.
Reviewed on Feb 23, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$101 nightly
The price is $113 total per night from Mar 7 to Mar 8
$113 total
Mar 7 - Mar 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. ...
9/10 Wonderful! (1,001 reviews)
Yes
Reviewed on Feb 15, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$84 nightly
The price is $92 total per night from Mar 6 to Mar 7
$92 total
Mar 6 - Mar 7
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! (1,000 reviews)
Staff were friendly and helpful. Room was clean, spacious and the bed was comfortable. Easy check in, convenient parking and the area felt safe
Reviewed on Feb 21, 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 Mar 15 to Mar 16
$109 total
Mar 15 - Mar 16
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! (1,000 reviews)
Great one night stay! Friendly, welcoming staff! Room was clean and comfortable. Location was perfect- near dining and highway!
Reviewed on Feb 27, 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?
Special
Hanover, District of Columbia, USA
$23
$78 total
found 20 hours ago
Standard
Hanover, District of Columbia, USA
$24
$80 total
found 20 hours ago
Fullsize
Baltimore, Maryland, USA
$25
$83 total
found 20 hours ago
Economy
Hanover, District of Columbia, USA
$29
$58 total
found 16 hours ago
Lowest prices found within the past 20 hours. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Plane Tickets To Winchester
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.
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
Explore More Ways to Travel with Travelocity
- Apartments in Berryville
- B&B in Berryville
- Cabins in Berryville
- Chalets in Berryville
- Cottages in Berryville
- Extended Stay Hotels in Berryville
- Romantic Getaways & Hotels in Berryville
- Berryville Hotels
- Motels in Berryville
- Hotels near Virginia River Trips
- Hotels near Abram's Delight
- Hotels near Nalls Farm Market
- Hotels near Jim Barnett Park
- Farmstay in Stephens City
- Apartments in Stephens City
- B&B in Stephens City
- Cabins in Stephens City
- Extended Stay Hotels in Stephens City
- Historic Hotels in Stephens City
- Hotels with Hot Tubs in Stephens City
- Luxury Hotels in Stephens City
- Pet Friendly Hotels in Stephens City
- Winery Hotels in Stephens City
- Stephens City Hotels
- Motels in Stephens City
- Rv Parks in Stephens City
- Resorts in Stephens City
- Hotels near Rocking S Ranch
- Hotels near Apple Blossom Mall
- Hotels near Patsy Cline Historic House
- Hotels near Rock Harbor Golf Course
- Hotels near Bright Box Theater
- Hotels near The Kernstown Battlefield
- 3 Star Hotels in Old Town Winchester
- Boutique Hotels in Old Town Winchester
- Golf Resorts & in Old Town Winchester
- Historic Hotels in Old Town Winchester
- Hotels with Balconies in Old Town Winchester
- Old Town Winchester Hotels
- Hotels near Shenandoah University
- Hotels near Dinosaur Land
- Hotels near Mt Hebron Cemetery
- Hotels near Winchester Medical Center
- 3 Star Hotels in Boyce
- B&B in Boyce
- Cabins in Boyce
- Luxury Hotels in Boyce
- Boyce Hotels
- Vacation Homes in Boyce
- Resorts in Boyce
- Villas in Boyce
- Apartments in White Post
- B&B in White Post
- Cabins in White Post
- Luxury Hotels in White Post
- Spa Resorts & in White Post
- Winery Hotels in White Post
- White Post Hotels
- Inns in White Post
- Hotels near Winchester-Frederick County Convention & Visitors Bureau
- Hotels near Winchester Regional
- Hotels near Mackintosh Fruit Farm
- Flights to Berryville
- Flights to Luray
- Flights to Woodstock
- Flights to Front Royal
- Flights to Syria
- Flights to Warrenton
- Flights to Sterling
- Flights to Paris
- Flights to Stephens City
- Flights to Nokesville
- Flights to Basye
- Flights to Herndon
- Flights to Upperville
- Flights to Boston
- Flights to Middleburg
- Flights to Edinburg
- Flights to Star Tannery
- Flights to Manassas
- Flights to Ashburn
- Flights to Skyland
- Flights to Airlie
- Flights to Purcellville
- Flights to Chantilly
- Flights to Reston
- Flights to Millwood
- Flights to Leesburg
- Flights to Boyce
- Flights to Centreville
- Flights to Northern Virginia
- Flights from Winchester Regional
- Flights to Haymarket