Shepherdstown Holidays
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Shepherdstown Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hyatt Place Baltimore Inner Harbor
Harbor East
S$1,176
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.4/10 Very good! (2,613 reviews)
Stayed 2 nights for a concert. The staff were incredibly nice and helpful, especially being fully booked and all the fans coming in and out. The room was very spacious, clean, and the bed was very comfortable. I loved how around the sink there was space to put my toiletries/makeup. Great things close by in the area as well and easy to get to places via transit/car. The parking fee is a bit exorbitant, but I get it given the proximity to the harbor, but there were other cheaper options nearby so it wasn't terrible.
Reviewed on 17 Aug, 2026
Rachael's Inner Harbor Boutique Inn
Ridgely's Delight
S$1,130
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.8/10 Excellent! (11 reviews)
We had a great time. Was in town for a baseball game and the location was great. The room was clean and very large. We will most likely be back next time the PHILLIES are in town.
Reviewed on 11 Aug, 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Fells Point
S$1,075
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
9.2/10 Wonderful! (835 reviews)
Top notch experience in a beautiful setting with nice touches, like warm chocolate chip cookies.
Reviewed on 17 Aug, 2026
Pier 5 Hotel Baltimore
Inner Harbor
S$1,012
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Salt Lake City (SLC) to Baltimore (BWI)
8.2/10 Very good! (1,339 reviews)
The facility was clean, but this beautiful hotel needs a facelift! A good facelift. It looks very old and outdated which made it seem dirty, which is unfortunate. It is located in a most beautiful area and houses two very nice restaurants. I really didn't interact with the staff that much, so I can't really speak on that too deeply. I did not like that there were not any DO NOT DISTURB signs. I did ask the night guy about it and asked him my room not be cleaned, to which he replied he would handle it. They came and cleaned anyway, and didn't even leave tissue paper, which I had to ask the night guy for that same night I asked housekeeping not to clean especially because I asked them not to clean, and he had to look very hard to find tissue paper. It looked like he might have borrowed a roll from somewhere. Not a big deal, but it kind of is at the same time. We ended up having to use Kleenex the last morning we were there. Also, the hallways, and elevators were VERY HOT. Would I stay there again-maybe. I now know what other options I have.
Reviewed on 17 Aug, 2026
Top hotels in Shepherdstown
Quality Inn Shepherdstown
70 Maddex Square Dr Shepherdstown WV
Fully refundable
S$145
13 Sept - 14 Sept
includes taxes & fees
8/10 Very good! (298 reviews)
"Nice room for the money, room was very clean, and free breakfast was ok but we never could figure out the TV remote."
Reviewed on 18 Aug, 2026
Country Inn & Suites by Radisson, Hagerstown, MD
17612 Valley Mall Rd Hagerstown MD
S$148
13 Sept - 14 Sept
includes taxes & fees
Country Inn & Suites by Radisson, Frederick, MD
5579 Spectrum Dr Frederick MD
Fully refundable
S$115
13 Sept - 14 Sept
includes taxes & fees
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.
Stay near popular Shepherdstown attractions
Shepherdstown Historic District
Wander through America's oldest West Virginia town, where 18th-century architecture tells stories from the 1730s. Explore German Street's unique shops and historic venues like the Shepherdstown Opera House.
Shepherdstown Museum
8.0/10 (1 review)
Housed in the historic Entler Hotel, this museum showcases Shepherdstown's rich past through local artefacts and documents. The James Rumsey Boathouse features a working replica of the inventor's pioneering steamboat.
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.
Scarborough Library
Scarborough Library houses over 158,000 volumes and serves as Shepherd University's academic heart. Its solar-paneled roof showcases the institution's commitment to sustainability while providing a research space.
Shepherdstown City Hall
This historic building serves as the administrative heart of Shepherdstown's charming historic district. Admire its regional architectural style while exploring nearby heritage sites and local shops.
Rumsey Steamboat Museum
2.0/10 (1 review)
This intimate museum showcases James Rumsey's revolutionary 1787 steamboat, predating Fulton by decades. Explore the working replica and a vivid historical mural depicting the original Potomac River demonstration.
Rumsey Monument
This 75-foot stone tribute honours James Rumsey, who demonstrated a steamboat in 1787, predating Fulton's famous vessel. From its hilltop perch, enjoy sweeping views of the Potomac River and Blue Ridge Mountains.
Bane Harris Community Park
Bane Harris Community Park is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? While you're in the area, stroll along the riverfront.
Frequently asked questions
How much does a Shepherdstown holiday package cost?
You'll find cheap prices from S$1,000 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?
- Choose your dates: What you'd like to do in Shepherdstown and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
