Shepherdstown Holidays from £742

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Your Shepherdstown Holiday

When you choose a Shepherdstown holiday package, you can really enjoy your adventure to the fullest. Delve into the highlights of this fascinating city knowing that all your travel needs have been taken care of in advance. You'll want to take in the sights during your trip to Shepherdstown. Carve out some time for popular attractions like Antietam National Battlefield, Shepherd University and Antietam National Cemetery. Whatever your travel plans or the size of your budget, organising a tailored Shepherdstown holiday is a breeze with Expedia.

The Latest Shepherdstown Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn National Airport/Crystal City by IHG

Holiday Inn National Airport/Crystal City by IHG

3.5 out of 5
Crystal City
per person
3 Sept - 9 Sept
found 7 hours ago
Return flight included
Glasgow (GLA) to Washington (DCA)
8.2/10 Very Good! (1,956 reviews)
Friendly staff. Smooth check-in and check-out. Hotel is a little dated and could use some upgrades (fresh paint, carpet, bathroom, etc)

Reviewed on 23 Jun 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
3 Sept - 9 Sept
found 7 hours ago
Return flight included
Glasgow (GLA) to Washington (DCA)
No reviews
My husband and I stayed here for our anniversary and it did not disappoint. We will definitely be coming back. The staff, the hotel, the restaurants- all absolutely amazing.

Reviewed on 22 Jun 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on 24 Jun 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.2/10 Wonderful! (598 reviews)
I like the fact that it was so close to the all of the attractions in town and close to the metro.

Reviewed on 24 Jun 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
1 Aug - 8 Aug
found 1 hour ago
Return direct flight included
London (LON) to Washington (DCA)
8.8/10 Excellent! (2,464 reviews)
Clean, excellent quality, friendly stuff. Restaurant is of an excellent quality, although maybe a little more expensive that I would expect. Good location for the purpose of my visit. Relatively far from the subway stations though; however buses are coming near.

Reviewed on 19 Jun 2025

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
per person
4 Aug - 11 Aug
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,001 reviews)
Never a disappointment. Staff are friendly and helpful. Everything is well taken care of.

Reviewed on 9 Jun 2025

Shepherdstown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Hagerstown Regional Airport (HGR)
Population
2,100
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Greenbrier State Park, Big Cork Vineyards and Bolivar Heights Scenic Overlook

Our pick of the best Shepherdstown Hotel Deals

Quality Inn Shepherdstown
Quality Inn Shepherdstown
2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
Stay at this hotel in Shepherdstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Maddex Square and Bane Harris Community Park are ...
7.6/10 Good! (137 reviews)
Did the job
"The manager went out of his way to make us feel welcome. Room was fine and breakfast spartan but serviceable."

Reviewed on 14 Jun 2025

Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown, WV
Stay at this cabin in Shepherdstown. Enjoy free Wi-Fi, a garden and patios. Popular attractions Rumsey Monument and Scarborough Library are located nearby.
9.8/10 Exceptional! (56 reviews)
"We truly loved this location and definitely will be back!"

Reviewed on 25 May 2025

❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Frederick, MD
Country Inn & Suites by Radisson, Frederick, MD
3 out of 5
5579 Spectrum Dr, Frederick, MD
Stay at this 3-star business-friendly hotel in Frederick. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,025 reviews)
"Management great & helpful. Lukewarm water for bath/shower."

Reviewed on 23 Jun 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 885 properties in Shepherdstown
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Shepherdstown holiday with Expedia?
Choose Expedia to arrange your next big break easily and all in one convenient place. Our top tip for scoring a fabulous deal on a Shepherdstown retreat? Bundle your flights, accommodation and/or hire car into a package holiday. Then add a few exciting tours and activities. Most bookings also include flexible cancellation policies, so there's no need to worry if you have to switch up your travel agenda. Round-the-clock assistance with making tweaks to your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Shepherdstown?
April, May and July are the busiest months in Shepherdstown, while November, December and January are generally quieter. With daytime average temperatures of 0ºC, January is the coolest period in Shepherdstown. The warmest time of year is July, when you can experience average temperatures of 24ºC during the day. Whatever the weather, you'll find loads to keep you busy here.
What is the top hotel for my holiday in Shepherdstown?
Create unforgettable memories in Shepherdstown by choosing Springhill Suites by Marriott Hagerstown as your home-away-from-home and gateway to fun and adventure.
How do I get a cheap holiday to Shepherdstown?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and hire cars --- we've got it all. Choose the combination that suits your style and watch your savings grow. We know holidays are never a one-size-fits-all. That's why Expedia offers over 400 airlines and 321,000 properties globally, which lets you customise your Shepherdstown holiday your way. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Shepherdstown holiday?
With popular attractions such as Antietam National Battlefield and Shepherd University, a holiday in Shepherdstown is filled with exciting places to visit. Big Cork Vineyards and Antietam National Cemetery are a couple of other sights worth discovering.
What is the best area to stay in when on holiday in Shepherdstown?
Shepherdstown has lots of interesting places to see, like Shepherd University. Stay somewhere nearby and make sightseeing stress-free.
Do I need a visa for my Shepherdstown holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the reason for your visit, whether it be for work or holidays, will determine if you'll need a visa for Shepherdstown. Also make sure your passport is up to date and has at least six months validity remaining after your return date. Do all your travel planning well in advance to avoid any nasty last-minute surprises.
What should I wear on my Shepherdstown holiday?
Although everyone's fashion style differs, it can be useful to have a few guidelines for what kind of clothes to wear during your holiday in Shepherdstown. We recommend looking up style blogs before you leave for inspiration on fashion trends or dress codes. Daytime temperatures in January, Shepherdstown's coolest month, average 0ºC. July marks this city's warmest month when the average temperature reaches 24ºC. Our tip? Take the guesswork out of what to pack and check the local weather conditions.
What does an Expedia Shepherdstown holiday include?
With Expedia, you can select a combination of hotels, flights and car hires to create your perfect Shepherdstown package. Once you've made your booking, simply add on all the fun stuff like sightseeing tours and activities. Remember --- the more you bundle, the more cash you'll save! Expedia features different types of properties, with the most sought after in Shepherdstown including private holiday homes and cottages. With Expedia, you'll always have the flexibility and freedom to tailor your holiday any way you want.
Does Expedia offer Book Now, Pay Later Shepherdstown holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:
  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • No-deposit holidays: Hitting the "book now" button is much easier with this plan. With no upfront fee for your holiday, you can Book Now, Pay Later and get on your way.

Can I choose my airline with a Shepherdstown Expedia holiday?
Yes --- that's one of the best things about an Expedia holiday package. You're the boss! We have access to more than 400 partner airlines throughout the world, so you have lots of choice when planning your Shepherdstown escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.