Cheap flights To Shepherdstown (FDK) from $53

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Cheap Flights to Shepherdstown from $53 One Way, $89 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Aug 28 - Mon, Aug 31
MYR
Myrtle Beach Intl.
HGR
Hagerstown Regional
$89 Roundtrip, found 18 hours ago
$89
Roundtrip
found 18 hours ago
Select Allegiant Air flight, departing Fri, Aug 28 from Myrtle Beach Intl. to Hagerstown Regional, returning Mon, Aug 31, priced at $89 found 18 hours ago
Fri, Aug 28 - Mon, Aug 31
MYR
Myrtle Beach Intl.
HGR
Hagerstown Regional
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Aug 28 from Myrtle Beach Intl. to Hagerstown Regional, returning Mon, Aug 31, priced at $96 found 1 day ago
Fri, Oct 2 - Mon, Oct 5
MYR
Myrtle Beach Intl.
HGR
Hagerstown Regional
$97 Roundtrip, found 4 days ago
$97
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Fri, Oct 2 from Myrtle Beach Intl. to Hagerstown Regional, returning Mon, Oct 5, priced at $97 found 4 days ago
Fri, Oct 23 - Mon, Oct 26
MYR
Myrtle Beach Intl.
HGR
Hagerstown Regional
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Oct 23 from Myrtle Beach Intl. to Hagerstown Regional, returning Mon, Oct 26, priced at $99 found 1 day ago
Fri, Oct 2 - Mon, Oct 5
MYR
Myrtle Beach Intl.
HGR
Hagerstown Regional
$106 Roundtrip, found 4 hours ago
$106
Roundtrip
found 4 hours ago
Select Allegiant Air flight, departing Fri, Oct 2 from Myrtle Beach Intl. to Hagerstown Regional, returning Mon, Oct 5, priced at $106 found 4 hours ago
Mon, Oct 5 - Mon, Oct 5
SFB
Orlando Sanford Intl.
HGR
Hagerstown Regional
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Mon, Oct 5 from Orlando Sanford Intl. to Hagerstown Regional, returning Mon, Oct 5, priced at $110 found 1 day ago
Fri, Oct 2 - Mon, Oct 5
SFB
Orlando Sanford Intl.
HGR
Hagerstown Regional
$115 Roundtrip, found 10 hours ago
$115
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Fri, Oct 2 from Orlando Sanford Intl. to Hagerstown Regional, returning Mon, Oct 5, priced at $115 found 10 hours ago
Sun, Dec 6 - Sun, Dec 13
PIE
St. Petersburg-Clearwater Intl.
HGR
Hagerstown Regional
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Sun, Dec 6 from St. Petersburg-Clearwater Intl. to Hagerstown Regional, returning Sun, Dec 13, priced at $115 found 1 day ago
Fri, Oct 9 - Mon, Oct 12
SFB
Orlando Sanford Intl.
HGR
Hagerstown Regional
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Fri, Oct 9 from Orlando Sanford Intl. to Hagerstown Regional, returning Mon, Oct 12, priced at $120 found 2 days ago
Mon, Sep 28 - Mon, Oct 5
SFB
Orlando Sanford Intl.
HGR
Hagerstown Regional
$125 Roundtrip, found 2 hours ago
$125
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Mon, Sep 28 from Orlando Sanford Intl. to Hagerstown Regional, returning Mon, Oct 5, priced at $125 found 2 hours ago

Shepherdstown Flight Information

Traveling To
Shepherdstown
Destination Airport IATA Code
FDK
Number of Airlines Serving
Airlines
Allegiant Air
Flight Price
$89
Earliest Departing Flight
Latest Departing Flight

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Shepherdstown economy flight packages

Price found within the past 48 hours. Click for updated prices.
The River Inn
4.0-star property

The River Inn

Sep 18 - Sep 21

3 night stay

Boston (BOS) to Baltimore (BWI)

JetBlue Airways • Roundtrip • Coach
Price was $549, price is now $402 per person
$402
per person
found 1 day ago
Hotel Burg
4.0-star property

Hotel Burg

Oct 2 - Oct 5

3 night stay

Boston (BOS) to Baltimore (BWI)

Southwest Airlines • Coach

Baltimore (BWI) to Boston (BOS)

Delta • Coach
Save 100% on your flight
Price was $1,605, price is now $1,034 per person
$1,034
per person
found 1 day ago
The LINE Hotel DC
4.5-star property

The LINE Hotel DC

Sep 18 - Sep 21

3 night stay

Boston (BOS) to Baltimore (BWI)

JetBlue Airways • Roundtrip • Coach
Price was $540, price is now $406 per person
$406
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Shepherdstown
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Shepherdstown first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Hive
3.5-star property

Hotel Hive

9.2/10 Wonderful! (1,553 reviews)

Sep 10 - Sep 14

4 night stay

Boston (BOS) to Baltimore (BWI)

United • Roundtrip • FirstClass
Price was $759, price is now $621 per person
$621
per person
found 1 day ago
"micro-hotel" for when you don't need all the bells and whistles but want a convenient place to stay ... staff was friendly ... you may need to ask for extra towels ... room was spacious/bathroom tiny -- but perfectly fine for our short length of stay ... very nicely-fragranced shower products ... if you are a light sleepr, consider traveling with a noise machine/ear plugs as it is still a city and there is a hospital near by ... while we did not eat in the restaurant, there was a steady stream of customers for pizza and the rooftop bar was popular

Reviewed on Aug 8, 2026

Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

9/10 Wonderful! (1,224 reviews)

Sep 10 - Sep 14

4 night stay

Boston (BOS) to Baltimore (BWI)

United • Roundtrip • FirstClass
Price was $1,122, price is now $907 per person
$907
per person
found 1 day ago

The River Inn
4.0-star property

The River Inn

9.4/10 Exceptional! (2,056 reviews)

Sep 10 - Sep 14

4 night stay

Boston (BOS) to Baltimore (BWI)

United • Roundtrip • FirstClass
Price was $788, price is now $640 per person
$640
per person
found 1 day ago
I was pleasantly surprised with the room's kitchen amenities and their accomodations for our dog! Even had a dog park walking distance from the hotel. Very cozy and perfect break from the road. Hotel is also accessible to most DC destinations.

Reviewed on Aug 8, 2026

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See all available trips from Boston to Shepherdstown
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Shepherdstown

Reach your destination without breaking your budget by booking your flights to Shepherdstown using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Shepherdstown Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Shepherdstown flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Shepherdstown. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Shepherdstown, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Shepherdstown flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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Frequently asked questions

Which airlines fly to Shepherdstown?
You can select from 20 airlines that fly into Washington Dulles Intl. Airport (IAD), the most popular airport in the city. With a good range of choice, you're bound to walk away with a superb deal. Here are a few of the preferred international carriers that'll get you to Shepherdstown — and then exploring every corner of this city:

  • United Airlines - 442 flights to Shepherdstown per month
  • Air Canada - 86 flights to Shepherdstown per month
  • Avianca - 73 flights to Shepherdstown per month

What is the best airport to fly to in Shepherdstown?
Hagerstown Regional Airport (HGR) is the entry point to the city, so the only thing you'll need to decide on will be the window seat or the aisle seat. The center of Shepherdstown is roughly 19 miles away and where many visitors choose to book a hotel.
How much is a flight to Shepherdstown?
Travelers from near and far bagged round-trip flight deals ranging between $89 and $125 this week to Shepherdstown. Starting your journey from Myrtle Beach (MYR)? The cheapest one-way tickets started at just $53.
How to book the cheapest flight to Shepherdstown?
With some of the biggest and best flight deals around, you're guaranteed value for money with Orbitz. The following useful tips will help you score cheap flights to Shepherdstown — and leave you with more cash to play with:

  • Consider departing from or arriving at nearby airports to increase your savings. Enter your preferred departure and arrival points in the form fields, then click on the 'Nearby airports' function below. It will list your options, if any.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' option. You'll see the flight deals for the days either side of your chosen departure. Airfares often vary depending on what day of the week it is.
  • Hit 'Show options' to filter your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • The early bird catches the most rewarding deals, so book your tickets the moment you know your travel dates. The cheapest fares go like hotcakes and prices generally increase as the departure date nears.
  • Combine your flights, hotels and car rental into a package deal and score great discounts. Save your hard-earned money for things you're really excited about, like exploring every corner of Shepherdstown.
  • Flying during the busy season means expensive airfares. Try to vacation outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

What is the best time to book a flight to Shepherdstown?
Pick up a bargain and book your seats to Shepherdstown in January. If you've missed this month, you're still in luck. February and August often have low airfares available, too. Just make sure you don't sleep on a sale — cheap flights pop up and disappear in the tap of a button!
What day of the week is the cheapest to book a flight to Shepherdstown?
To pick up an incredible flight deal, book on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days to purchase tickets to Shepherdstown.
What is the cheapest day of the week to fly to Shepherdstown?
Consider departing early in the week to get cheap flights to Shepherdstown. Orbitz data from 2020 shows Monday is generally the most inexpensive day to hop on a plane, followed by Tuesday. Saturday was found to have the most expensive airfares. Presumably, this is because many travelers choose to begin their trip on a weekend.
What is the cheapest month to fly to Shepherdstown?
Get set to jet for less in August. This is generally an excellent month to get on a plane if you're looking for cheap flights to Shepherdstown, Orbitz data shows. The least affordable time to fly is June, so avoid this month if you're watching your pennies.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find carriers offering fare flexibility. Simply choose "Filter by flexible change policies" when searching for your Shepherdstown flights and ta-da! We'll show you options that include free cancellation, no change fees and of course, the best price.
What do I need for the flight to Shepherdstown?
Flying can be a joy with a bit of pre-planning! Make your flight a relaxing one with the following practical tips:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some kind of government-issued photo identification. If you're traveling internationally, make sure your passport is valid and you've looked into visa requirements.
  • Take some activities to keep you amused on your trip to Shepherdstown. Books, magazines and electronic gadgets like tablets and e-readers are ideal. Make sure you take a bottle of water with you too. Even on a short flight, it's important to stay well-hydrated.
  • Even if you're flying in the height of summer, bring a sweater or cardigan on board with you. Airplane cabins can get chilly!

How many direct flights are there to Shepherdstown?
Approximately 0 per month. Allegiant Air is among the carriers that offer direct flights to Shepherdstown. Use the Orbitz search tool to work out if Allegiant Air has any nonstop fares from your point of departure.
How do I get cheap first-class/business deals to Shepherdstown?
There are ways of booking first or business-class airfares to Shepherdstown that won't burn through your wallet. Pick up a seat at the front of the plane for less with these helpful tips:

  • Be flexible. By being open to a few travel dates, you'll have a better chance of landing a deal on your airfares.
  • Plenty of low-cost airlines these days have excellent business or premium-class seating without the hefty fees.
  • Bid for an upgrade in online auctions or upgrade your ticket through your loyalty program.

What is the best time to go to Shepherdstown?
Shepherdstown is a wonderful year-round vacation destination, but the most popular months are April, May and August. If you love warmer weather, head there in summer. Like most places in the Northern Hemisphere, the summer season gets underway June 20. Temperatures normally float between 65 ºF and 85 ºF during the daytime.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.