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.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $836, price is now CA $618 per person
CA $618
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,022 reviews)
This is a safe, nice hotel on a college campus in a great location of DC. The staff was friendly and professional. The only thing we had an issue is with allergies. Seemed like a dust issue as the rooms all have the air conditioning with recycled air. Overall great property.

Reviewed on Jun 15, 2026

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was CA $1,064, price is now CA $764 per person
CA $764
per person
Aug 13 - Aug 17
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,866 reviews)
We stay here every time we come into Annapolis. It’s a wonderful Hotel wonderful staff and a great location.

Reviewed on Jun 23, 2026

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Tysons
Price was CA $1,653, price is now CA $1,249 per person
CA $1,249
per person
Jul 30 - Aug 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,009 reviews)
Elevator operation is very inefficient. Face wash drainage is somehow plugged.

Reviewed on May 22, 2026

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Price was CA $2,508, price is now CA $1,933 per person
CA $1,933
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9.2/10 Wonderful! (208 reviews)
Great location. Great restaurant. Not too busy. Rooms are well appointed although showing some wear. I will be back.

Reviewed on Jun 15, 2026

Rachael's Inner Harbor Boutique Inn

Rachael's Inner Harbor Boutique Inn

3 out of 5
Ridgely's Delight
Price was CA $1,215, price is now CA $938 per person
CA $938
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
10/10 Exceptional! (4 reviews)
Everything was great!

Reviewed on Jun 16, 2026

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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 $135 per night from Jul 5 to Jul 6
CA $135
CA $151 total
Jul 5 - Jul 6
includes taxes & fees
8/10 Very good! (253 reviews)
"Staff was very nice, place was clean and well maintained. Room was also quiet for peaceful sleeping. Parking lot was well lit."

Reviewed on Jun 22, 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 $102 per night from Jul 13 to Jul 14
CA $102
CA $200 total
Jul 13 - Jul 14
includes taxes & fees
❤️ 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 $147 per night from Jul 20 to Jul 21
CA $147
CA $164 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,303 reviews)
"Excellent stay"

Reviewed on Jun 22, 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 948 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.
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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

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