Shepherdstown Vacation Packages

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Your Shepherdstown Vacation

When you choose a Shepherdstown vacation 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, organizing a tailored Shepherdstown vacation is a breeze with Expedia.

Top Shepherdstown Vacation Deals

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

Hotel Arboretum

2 out of 5
Northeast
Price was CA $701, price is now CA $465 per person
CA $465
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
8/10 Very Good! (968 reviews)
People camping on the medium strip between highways. Stranger in front of hotel door cornered me and talked for over 30 minutes when all I wanted to do is get in my room and chill.

Reviewed on Aug. 18, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was CA $1,310, price is now CA $800 per person
CA $800
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
9.8/10 Exceptional! (28 reviews)
Accommodating staff,professional,pleasant. Clean,I’d stay again!

Reviewed on Aug. 20, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,462, price is now CA $943 per person
CA $943
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on Jul. 21, 2025

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Price was CA $2,795, price is now CA $1,862 per person
CA $1,862
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (WAS)
9.2/10 Wonderful! (187 reviews)
Enjoyed my stay here. Our room was spacious. The staff were friendly. A lovely staff member named Abrehet was most especially helpful, and accommodating! Will be back.

Reviewed on Jul. 8, 2025

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Price was CA $946, price is now CA $643 per person
CA $643
per person
Sep 19 - Sep 23
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
this was a well-priced hotel and we found it to be cute and homey- sort of like you were at a beach hotel. Happy vibes:)

Reviewed on Aug. 17, 2025

Ready to book your vacation to Shepherdstown?

 

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Shepherdstown Hotel Deals

Quality Inn Shepherdstown

Quality Inn Shepherdstown

2.5 out of 5
70 Maddex Square Dr, Shepherdstown, WV
Fully refundable
The price is CA $133 per night from Sep 7 to Sep 8
CA $133
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
7.6/10 Good! (161 reviews)
"Please step up the breakfast game, it is sub-par, and the coffee is not drinkable."

Reviewed on Aug. 17, 2025

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

❤️ Secluded 1940s Romantic Tiny House on the River

Shepherdstown
The price is CA $92 per night from Sep 1 to Sep 2
CA $92
CA $187 total
Sep 1 - Sep 2
includes taxes & fees
9.8/10 Exceptional! (57 reviews)
"I left the children’s age for a purpose. Because y’all made us feel like we were high school kids again. Absolutely gorgeous views for a step up from tent camping. We will be back thank you"

Reviewed on Aug. 3, 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 CA $119 per night from Aug 27 to Aug 28
CA $119
CA $132 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (1,088 reviews)
"Front desk staff were welcoming & friendly. Many dining options nearby. Convenient location. Room was clean. Breakfast was typical-waffles eggs sausage potatoes pastrues yogurt etc Coffee available throughout the stay. Beds wete comfortable with ample pillows and extra blankets. Overall a nice ..."

Reviewed on Aug. 16, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Shepherdstown

Morgan's Grove Park

Morgan's Grove 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, find time to visit its casinos.

Morgan's Grove Park

Frequently asked questions

How much does a Shepherdstown vacation package cost?
You'll find cheap prices from CA $465 on Expedia for your Shepherdstown break. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Shepherdstown costs.
What are the cheapest months to go to Shepherdstown?
The off-season is the best time to visit Shepherdstown if you're trying to keep costs down. Another tip for scoring cheap Shepherdstown vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Shepherdstown?
With a well-organized travel plan, you can easily visit the main Shepherdstown attractions in a few days. But if you want to discover lesser-known spots or take day trips, consider booking your Shepherdstown vacation for longer.
Is it worth booking a vacation package to Shepherdstown?
Shepherdstown has everything you need for an unforgettable escape. Get your Shepherdstown vacation off to a flying start by visiting popular attractions like Shepherdstown Visitors Centre.
How to find the best Shepherdstown package deals?
Landing a cheap Shepherdstown package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Shepherdstown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Shepherdstown vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can tailor your Shepherdstown escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Shepherdstown?
If you have your Shepherdstown vacation dates confirmed, book early to snap up some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Shepherdstown?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Shepherdstown.
  2. Budget wisely: In addition to the cost of your accommodations, you should consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Shepherdstown.
  3. Work out your trip length: Consider how much time you'd like to spend discovering Shepherdstown. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Shepherdstown vacation package that brings all your bookings together.

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