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.
Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
Price was CA $1,000, price is now CA $778 per person
CA $778
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
8.8/10 Excellent! (1,902 reviews)
Rooms were very clean. Only had trouble with tv

Reviewed on Jul 8, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,096, price is now CA $1,403 per person
CA $1,403
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (81 reviews)
Excellent stay in a quiet area, but still plenty to do

Reviewed on Jul 8, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,141, price is now CA $861 per person
CA $861
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
8.2/10 Very good! (1,005 reviews)
Excellent environment within auniversity. Clean and decent hotel with nice staff.

Reviewed on Jul 7, 2026

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Tysons
Price was CA $1,207, price is now CA $927 per person
CA $927
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)
Serene

Reviewed on Jun 28, 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Price was CA $1,020, price is now CA $793 per person
CA $793
per person
Aug 23 - Aug 26
found 12 hours ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (2,206 reviews)

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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 $155 per night from Jul 26 to Jul 27
CA $155
CA $173 total
Jul 26 - Jul 27
includes taxes & fees
8/10 Very good! (265 reviews)
"Nice, small town atmosphere. Quiet and Clean in rooms and common areas. Friendly and helpful staff. Location near shopping, gas, restaurants, and activities. Gently working on updating some services."

Reviewed on Jul 7, 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 CA $96 per night from Jul 22 to Jul 23
CA $96
CA $193 total
Jul 22 - Jul 23
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 Jun 13, 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 CA $153 per night from Aug 9 to Aug 10
CA $153
CA $171 total
Aug 9 - Aug 10
includes taxes & fees
8.6/10 Excellent! (1,299 reviews)
"the hotel was clean and easy yocheck in."

Reviewed on Jul 8, 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 954 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
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Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/10 (1 review)
Enjoy a performance at Shepherdstown Opera House, a theater with a story to tell in Shepherdstown. Stroll along the riverfront or seek out the horseback riding.
See properties

Frequently asked questions

How much does a Shepherdstown vacation package cost?
You'll find cheap prices from CA $778 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.

Explore a world of travel with Expedia

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