Shepherdstown Holidays

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Top Flight + Hotel Deals in Shepherdstown

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
16 Oct - 19 Oct
found 20 hours ago
Return direct flight included
London (LON) to Washington (DCA)
8/10 Very Good! (968 reviews)
Staff was nice. Hotel is in deperate need of an upgrade

Reviewed on 10 Aug 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
16 Oct - 19 Oct
found 20 hours ago
Return direct flight included
London (LON) to Washington (WAS)
9.4/10 Exceptional! (1,510 reviews)
I love the quiet, modern style that the Lyle offers. The staff is helpful.

Reviewed on 10 Aug 2025

Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
per person
16 Oct - 19 Oct
found 20 hours ago
Return direct flight included
London (LON) to Washington (DCA)
9/10 Wonderful! (1,167 reviews)
Loved everything about this property.

Reviewed on 10 Aug 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
16 Oct - 19 Oct
found 20 hours ago
Return direct flight included
London (LON) to Washington (DCA)
9.2/10 Wonderful! (790 reviews)
The front desk staff were always so super nice. The rooms were nice and so was the bathroom. Everything was in very nice condition and clean. I hate how much resort fees can be and urban fees on top of that too lol. The only thing we didn’t like is that front desk and email confirmation said that checkout was 12pm but cleaning staff said it was 11am and we had to check out immediately because it was a bit past 11am. So I don’t know what is right. But I’m going off of the confirmation messages/emails and front desk. Something is out of sync there

Reviewed on 11 Aug 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
16 Oct - 19 Oct
found 20 hours ago
Return direct flight included
London (LON) to Washington (DCA)
8.8/10 Excellent! (1,624 reviews)
Second floor of the hotel was super noisy, could hear doors slamming, traffic, people shouting and water running in other rooms.

Reviewed on 10 Aug 2025

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 €92 per night from 7 Sept to 8 Sept
€92
7 Sept - 8 Sept
includes taxes & fees
7.6/10 Good! (157 reviews)
"Staff were very warm, friendly and efficient. Hotel was renovated recently, comfortable beds and everything felt fresh."

Reviewed on 7 Aug 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is €127 per night from 1 Sept to 2 Sept
€127
1 Sept - 2 Sept
includes taxes & fees
9.8/10 Exceptional! (57 reviews)
We loved this place!
"This place is peaceful and secluded the bed was comfortable and the air conditioner kept it comfortable you have everything you need to heat up food or keep it cold the view of the river is great and we enjoyed setting on the porch and watching the river and deers that walk right through the yard! ..."

Reviewed on 8 Jul 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
Fully refundable
The price is €81 per night from 17 Aug to 18 Aug
€81
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,073 reviews)
"Hotel was dated. Bathroom could use makeover but overall was clean."

Reviewed on 7 Aug 2025

Country Inn & Suites by Radisson, Frederick, MD
See all 888 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.

Frequently asked questions

How much does a Shepherdstown holiday package cost?
You'll find cheap prices from €596 on Expedia for your Shepherdstown getaway. However, a range of factors like the hotel choice, length of stay and season will determine how much your holiday to Shepherdstown costs.
What are the cheapest months to go to Shepherdstown?
Plan your getaway for the low season and you're likely to score cheap Shepherdstown holiday packages. Keep in mind that public holidays and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Shepherdstown?
With a well-organised itinerary, you can easily hit the most popular Shepherdstown sights in a few days. But if you want to explore off the beaten track or go on day tours, think about booking your Shepherdstown holiday for longer.
Is it worth booking a holiday package to Shepherdstown?
It's easy to see why a Shepherdstown holiday is on the must-do list of many travellers. Popular attractions like Shepherdstown Visitors Centre are just the beginning of what you can explore here.
How to find the best Shepherdstown package deals?
Begin your search for a Shepherdstown package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shepherdstown package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Shepherdstown escape off to a flying start.
Is it cheaper to book a Shepherdstown holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customised Shepherdstown holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Shepherdstown?
Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Shepherdstown break.
How to plan a trip to Shepherdstown?

  1. Choose your dates: What you'd like to do in Shepherdstown and your favourite season can help you decide when to go.
  2. Plan your budget wisely: On top of the price of your hotel, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Shepherdstown.
  3. Decide how long to go away for: Now that you're more familiar with Shepherdstown, you can work out the right length of your break. Pull together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Shepherdstown holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.