Shepherdstown Holidays

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Shepherdstown Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Furnished Apartments

Furnished Apartments

3 out of 5
Ashton Heights
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Washington (DCA)
9/10 Wonderful! (4 reviews)
The Westin Crystal City Reagan National Airport

The Westin Crystal City Reagan National Airport

4 out of 5
Crystal City
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Excellent service, location, staff, cleanliness, shuttle service to Reagan Airport.

Reviewed on 22 Jun, 2025

Apartments at the Heart of Arlington

Apartments at the Heart of Arlington

3.5 out of 5
Ballston
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Washington (DCA)
9/10 Wonderful! (6 reviews)
Nice place, parking was easy to get in front of the property on the street. Supplies were very limited in the apartment. We had to rush to nearby 7-11 multiple times to get supplies for bathroom as all those were limited in the quantity and ran out in 1-2 days and we had to stay there for 4-5 days.

Reviewed on 27 May, 2025

Elegant Apartments Near the Pentagon

Elegant Apartments Near the Pentagon

3.5 out of 5
Crystal City
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Washington (DCA)
10/10 Exceptional! (3 reviews)
Amazingly easy access and safe.

Reviewed on 31 Oct, 2024

Crystal City Comfortable Apartments

Crystal City Comfortable Apartments

3.5 out of 5
Crystal City
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Washington (DCA)
10/10 Exceptional! (3 reviews)
We loved this rental! The host called us on our way to confirm and we had great communication during our entire stay. Keys were easy to find, paid parking pass was worth it (though there was plenty of street parking), convenient store in the basement, and very hot water which I LOVED! My family of 5 was able to comfortably sprawl out and enjoy ourself. Thank you Margarita! Your home was so lovely.

Reviewed on 4 Jun, 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 S$120 per night from 6 Jul to 7 Jul
S$120
6 Jul - 7 Jul
includes taxes & fees
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
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 S$113 per night from 2 Jul to 3 Jul
S$113
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,029 reviews)
Highly recommended
"I would highly recommend this hotel. It was a great stay."

Reviewed on 25 Jun, 2025

Country Inn & Suites by Radisson, Frederick, MD
Clarion Inn Harpers Ferry - Charles Town
Clarion Inn Harpers Ferry - Charles Town
2.5 out of 5
4328 William L Wilson Fwy, Harpers Ferry, WV
Fully refundableReserve now, pay when you stay
The price is S$132 per night from 27 Jul to 28 Jul
S$132
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (1,014 reviews)
"This hotel has really friendly staff, thoughtful touches like magazines in the lobby, the ability to store our stuff for a couple hours after checkout, and a solid breakfast buffet but the rooms are a little run down."

Reviewed on 26 Jun, 2025

Clarion Inn Harpers Ferry - Charles Town
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.

Frequently asked questions

How much does a Shepherdstown holiday package cost?
You'll find cheap prices from S$1,983 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.