Shepherdstown Holidays from £1,275

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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.

Top Shepherdstown Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was £1,764, price is now £1,275 per person
£1,275
per person
24 Sept - 30 Sept
found 20 hours ago
Return flight included
Edinburgh (EDI) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
The property staff was awesome. Had a problem with TV and never fixed but staff did offer a change of rooms which I did not accept.

Reviewed on 11 Jul 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was £2,320, price is now £1,597 per person
£1,597
per person
24 Sept - 30 Sept
found 20 hours ago
Return flight included
Edinburgh (EDI) to Baltimore (BWI)
9.4/10 Exceptional! (1,196 reviews)
The hotel is very nice. We were greeted by Adrianne who was very polite and super friendly. Room was bigger than I expected and very clean and modern with lots of USB ports. Great drinks and staff at the restaurant. Great location too. We will return

Reviewed on 10 Jul 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £2,101, price is now £1,562 per person
£1,562
per person
24 Sept - 30 Sept
found 20 hours ago
Return flight included
Edinburgh (EDI) to Baltimore (BWI)
9/10 Wonderful! (1,206 reviews)
Poco confortable

Reviewed on 11 Jul 2026

The Bellmoor Inn & Spa

The Bellmoor Inn & Spa

4 out of 5
South Rehoboth
Price was £2,078, price is now £1,545 per person
£1,545
per person
27 Aug - 2 Sept
found 1 day ago
Return direct flight included
London (LGW) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
We loved our stay! The location is fantastic you can easily walk to most of the local shops, restaurants, so there’s really no need for a car for everything. The property was so cute and cozy. The staff had great customer service, which is something you don’t find very often anymore. They were also very accommodating of my service dog. We’ll definitely be back!

Reviewed on 10 Jul 2026

Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was £4,134, price is now £3,082 per person
£3,082
per person
24 Sept - 30 Sept
found 20 hours ago
Return flight included
Edinburgh (EDI) to Baltimore (BWI)
9.6/10 Exceptional! (1,002 reviews)
We had breakfast and dinner at the motel and the manager on duty made us welcome. He remembered our first names as we walked in for two breakfast and two dinners. He was in military as I also served. Check in manager made us welcome and parking garage I took two trips to truck and was helped tremendously. Bell hop gave me information on our plan of touring. Stayed at lot of motels being 70 years old and this place is Best of best and will be back. Thank You!

Reviewed on 12 Jul 2026

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

Top hotels in Shepherdstown

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr Shepherdstown WV
Fully refundable
The price is £82 per night from 3 Aug to 4 Aug
£82
3 Aug - 4 Aug
includes taxes & fees
8/10 Very good! (267 reviews)
"They had to move me because they put me in a room with a faulty TV. The clerk knew the TV in the first room had a problem the day before. The TV that worked was difficult to tune to a station I wanted to watch."

Reviewed on 11 Jul 2026

Quality Inn Shepherdstown
❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is £108 per night from 3 Aug to 4 Aug
£108
3 Aug - 4 Aug
includes taxes & fees
9.6/10 Exceptional! (79 reviews)
"This was a perfect place to relax and enjoy some quiet time! Loved the location and place was clean!"

Reviewed on 13 Jun 2026

❤️ Secluded 1940s Romantic Tiny House on the River
Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd Hagerstown MD
Fully refundable
The price is £87 per night from 4 Aug to 5 Aug
£87
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,302 reviews)
"The hotel is near lots of restaurants and a mall. It was close to the highway and a convenient stop in our travels."

Reviewed on 12 Jul 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 962 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
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Family Friendly Holidays

Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/10 (1 review)
This intimate historic theatre hosts diverse performances from indie films to live music in a beautifully preserved setting. Arrive early to enjoy Shepherdstown's dining scene before your show.
See properties

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.

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* 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.