Cheap Flights to Winchester from $19
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 $38 and $19 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$41 Roundtrip, found 22 hours ago
$41
Roundtrip
found 22 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chantilly | November 10 to November 17 | $38 |
| ATL | Baltimore | December 5 to December 12 | $50 |
| DFW | Chantilly | November 5 to November 9 | $54 |
| CLT | Baltimore | December 3 to December 6 | $91 |
| ATL | Washington | November 12 to November 17 | $132 |
| FLL | Washington | October 29 to November 3 | $135 |
| CLT | Chantilly | November 11 to November 12 | $160 |
| BOS | Chantilly | December 11 to December 13 | $162 |
| DAL | Washington | October 30 to November 2 | $195 |
| LAX | Baltimore | November 10 to November 11 | $203 |
| CLT | Washington | October 31 to November 3 | $212 |
| SFO | Washington | November 14 to November 16 | $264 |
| SFO | Baltimore | November 17 to November 23 | $285 |
| FCO | Chantilly | November 17 to December 1 | $547 |
| FCO | Baltimore | October 21 to November 3 | $616 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| FLL | Chantilly | October 10 to October 16 | $209 |
| FLL | Washington | October 10 to October 28 | $257 |
| FLL | Baltimore | October 10 to October 11 | $337 |
| CLT | Baltimore | October 10 to October 12 | $342 |
| BOS | Baltimore | October 11 to October 14 | $413 |
| LAX | Chantilly | October 11 to October 27 | $433 |
| CLT | Washington | October 11 to October 14 | $475 |
| SFO | Chantilly | October 11 to October 14 | $514 |
| BOS | Washington | October 10 to October 13 | $534 |
| DAL | Washington | October 10 to October 17 | $561 |
| LAX | Washington | October 10 to October 16 | $803 |
| ATL | Baltimore | October 10 to October 12 | $1,058 |
| FCO | Baltimore | October 11 to January 6 | $1,170 |
| BOS | Chantilly | October 10 to October 12 | $1,379 |
| FCO | Chantilly | October 11 to January 6 | $1,420 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $38 |
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 Nov 3 to Nov 4
$77 total
Nov 3 - Nov 4
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $78 total per night from Oct 12 to Oct 13
$78 total
Oct 12 - Oct 13
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! (1,079 reviews)
"Much too many emails from Expedia. Can you cut them back? Just a little?"
Reviewed on Oct 8, 2026
Twi-Lite Inn
53 West 14th Street Front Royal VA
$85 nightly
The price is $95 total per night from Oct 11 to Oct 12
$95 total
Oct 11 - Oct 12
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! (584 reviews)
"For the price, I'm very satisfied with the lodging. I used the microwave, refrigerator, and TV. The wifi was ok for my phone but to get good streaming, I relied on my own 5G plan. Parking right to the door so very convenient. The staff at the registration desk was welcoming and informative. Bedding ..."
Reviewed on Oct 6, 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
$68 nightly
The price is $77 total per night from Nov 3 to Nov 4
$77 total
Nov 3 - Nov 4
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. ...
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
$71 nightly
The price is $78 total per night from Oct 12 to Oct 13
$78 total
Oct 12 - Oct 13
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! (1,079 reviews)
"Much too many emails from Expedia. Can you cut them back? Just a little?"
Reviewed on Oct 8, 2026
Wayside Inn
7783 Main St Middletown VA
$94 nightly
The price is $104 total per night from Oct 19 to Oct 20
$104 total
Oct 19 - Oct 20
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! (449 reviews)
"Charmingly beautiful hotel. Like staying in a Civil War museum. Comfortable mattress. Slightly creaky bed. Got to hear the haunted boots on the wooden floor footsteps! Cute coffee shop next door. Will gladly be back!"
Reviewed on Sep 27, 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
$92 nightly
The price is $102 total per night from Nov 8 to Nov 9
$102 total
Nov 8 - Nov 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! (1,001 reviews)
"We have family in the area and this hotel has become our go-to. It’s always clean, the staff are friendly, and the breakfast is good. If you get a room facing the highway, it can be a little noisy during the day, but the traffic really slows down at night. It’s walking distance to local restaurants ..."
Reviewed on Oct 7, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
33760 Old Valley Pike Strasburg VA
$101 nightly
The price is $113 total per night from Nov 1 to Nov 2
$113 total
Nov 1 - Nov 2
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)
"Friendly"
Reviewed on Sep 29, 2026
Quality Inn Winchester
1601 Martinsburg Pike Winchester VA
$83 nightly
The price is $93 total per night from Nov 8 to Nov 9
$93 total
Nov 8 - Nov 9
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 ...
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Front Royal
9800 Winchester Rd Front Royal VA
$118 nightly
The price is $132 total per night from Nov 1 to Nov 2
$132 total
Nov 1 - Nov 2
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! (1,001 reviews)
"Clean and good breakfast"
Reviewed on Oct 1, 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.
Don't see what you're looking for?
See all available trips from Los Angeles to Winchester
View all tripsWinchester flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Mini Van
Baltimore, Maryland, USA
$58
$165 total
found 3 days ago
Economy
Baltimore, Maryland, USA
$59
$166 total
found 3 days ago
Special
Baltimore, Maryland, USA
$59
$166 total
found 3 days ago
Compact
Baltimore, Maryland, USA
$59
$166 total
found 3 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
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
- Hotels near Bright Box Theater
- Hotels in Berryville
- 5 Star Hotels in Winchester
- 4 Star Hotels in Winchester
- Villas in Winchester
- Motels in Winchester
- Hotels in Winchester
- Winery in Winchester
- The George Washington Hotel A Wyndham Grand Hotel
- Spa in Winchester
- Sleep Inn & Suites Winchester near University
- Ski in Winchester
- Romantic in Winchester
- Pet Friendly in Winchester
- Motel 6 Winchester VA
- Microtel Inn & Suites by Wyndham Winchester
- Luxury in Winchester
- Kitchenette in Winchester
- Indoor Pool in Winchester
- Hot Tub in Winchester
- Free Parking in Winchester
- Free Breakfast in Winchester
- Bar in Winchester
- Balcony in Winchester
- Pool in Winchester
- Early Check-in in Winchester
- Historical in Winchester
- Golf in Winchester
- Family Friendly in Winchester
- Budget in Winchester
- Casino in Winchester
- Boutique in Winchester
- Beach in Winchester
- APM Inn & Suites
- Aparthotels in Winchester
- Cottages in Winchester
- Cabins in Winchester
- Bedandbreakfast in Winchester
- Apartments in Winchester
- Agritourism in Winchester
- Hotels near Washington DC
- Hotels in Strasburg
- Hotels in Stephens City
- Hotels near Shenandoah University
- Hotels near Shenandoah National Park
- Old Town Winchester Hotels
- Balcony Hotels in Old Town Winchester
- Historical Hotels in Old Town Winchester
- Boutique Hotels in Old Town Winchester
- Hotels in Middleburg
- Salamander Resort And Spa
- Hotels in Luray
- Hotels near Luray Caverns
- Hotels in Leesburg
- Lansdowne Resort and Spa
- Hotels near George Washington's Office
- Hotels in Front Royal
- Hotels near Front Royal Entrance Shenandoah National Park
- Flights to Paris
- Flights to Northern Virginia
- Flights to Nokesville
- Flights to Millwood
- Flights to Middleburg
- Flights to Manassas
- Flights to Luray
- Flights to Leesburg
- Flights to Herndon
- Flights to Haymarket
- Flights to Front Royal
- Flights to Fairfax
- Flights to Culpeper
- Flights to Clifton
- Flights to Chantilly
- Flights to Centreville
- Flights to Boyce
- Flights to Boston
- Flights to Berryville
- Flights to Ashburn
- Flights to Airlie
- Flights from Winchester VA
- Flights from Washington DC
- Flights to Woodstock
- Flights to Warrenton
- Flights to Vienna
- Flights to Syria
- Flights to Sterling
- Flights to Stephens City
- Flights to Skyland
- Flights to Reston
- Flights to Purcellville