Shepherdstown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
8.8/10 Excellent! (1,340 reviews)
Great place to stay in the heart of Georgetown.

Reviewed on Jun. 2, 2024

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
9.2/10 Wonderful! (1,001 reviews)
Melody had talked to my mother and travel partner for this trip about our questions prior to going. She met us at check in and it was a great addition to all of the very friendly staff. The breakfast buffet was ok but not worthy of the cost in my opinion.

Reviewed on Jun. 4, 2024

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
The Watergate is a great property, you can tell it looks a little aged and in need of renovations. Overall we enjoyed our stay.

Reviewed on Jun. 2, 2024

InterContinental Washington D.C. - The Wharf, an IHG Hotel

InterContinental Washington D.C. - The Wharf, an IHG Hotel

5 out of 5
The Wharf
per person
Jul. 18 - Jul. 21
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
9.2/10 Wonderful! (1,003 reviews)
Staff were great! Room was great! Location was great!

Reviewed on Jun. 4, 2024

Shepherdstown Hotel Deals

❤️ Secluded 1940s Romantic Tiny House on the River
❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
The price is CA $103 per night from Jun. 16 to Jun. 17
CA $103
CA $197 total
includes taxes & fees
Jun 16 - Jun 17
9.8/10 Exceptional! (41 reviews)
Excellent stay at The River House
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, ..."

Reviewed on Apr. 14, 2024

❤️ 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 $109 per night from Jun. 10 to Jun. 11
CA $109
CA $121 total
includes taxes & fees
Jun 10 - Jun 11
8.4/10 Very Good! (1,008 reviews)
"Not fancy, but clean and convenient."

Reviewed on Jun. 5, 2024

Country Inn & Suites by Radisson, Frederick, MD
Hilton Garden Inn Frederick
Hilton Garden Inn Frederick
3 out of 5
7226 Corporate Ct, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jun. 23 to Jun. 24
CA $138
CA $153 total
includes taxes & fees
Jun 23 - Jun 24
8.8/10 Excellent! (1,005 reviews)
"Comfortable. Friendly staff. Thank Antoinette for being very kind during the check-in process."

Reviewed on Jun. 5, 2024

Hilton Garden Inn Frederick
See all 779 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

Frequently asked questions

How much does a Shepherdstown vacation package cost?
From as low as CA $995. Yes, you read that right. Our Shepherdstown packages are an awesome way to stretch your budget. Bundle your preferred flights, hotels and rental car and explore this fabulous destination.
How do I get a cheap travel package to Shepherdstown?
Imagine all the wonderful things you could do in Shepherdstown with a pile of extra cash in your wallet. Watch your savings stack up when you combine your hotel and airfare bookings into a Shepherdstown vacation package. You have plenty of choice when you book your trip with Expedia too. In fact, you can take your pick of more than 550 airlines and 1,000,000 properties globally. Whether you’re taking off with the whole family or traveling with someone special, planning a trip to Shepherdstown is better with a package.
Where should I stay in Shepherdstown?
A vacation in Shepherdstown wouldn’t be complete without stopping by Shepherd University, Shepherdstown Visitors Center and Shepherdstown Opera House. Spend your evenings near these popular sights and make sightseeing simple.
What are the top hotels in Shepherdstown?
Stunning Custom Shepherdstown Waterfront Retreat and Cabin - Secluded 1940s Romantic Tiny House On The River are two of the most well-known hotels in Shepherdstown. Why not check out the facilities and rates at each and then make up your mind?
How far in advance should I book my Shepherdstown vacation?
To bag discount prices, book as soon as you can. Airlines generally release flight tickets, along with some of the lowest fares, nearly 12 months prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway to Shepherdstown, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Shepherdstown travel package include?
Hotels, flights and car rentals — we bring you the very best bargains. All you have to do is pick your ideal combination. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it easy to create an awesome Shepherdstown getaway.
What should I know before booking a Shepherdstown travel package?
When you book your flights, hotels and car rentals together, you’ll be rewarded with terrific discounts. Whether you’re organizing a mountain getaway in a cabin or would rather stay in a luxurious city hotel, Expedia will make it happen for less.
Can I choose my airline with a Shepherdstown Expedia vacation package?
You can, and with over 550 airlines to pick from throughout the world, you have plenty of choice. Look through the available options and see which airline suits your needs and budget.
If I'm not able to travel, can I cancel my Shepherdstown vacation package?
You can cancel your Shepherdstown booking if your plans have been upended. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Shepherdstown

Image for Shepherd University

Shepherd University

Explore the campus of Shepherd University, during your travels in Shepherdstown. Amble around the area's riverfront, or seek out its horseback riding.

Shepherd University
Image for Shepherdstown Visitors Center

Shepherdstown Visitors Center

Shepherdstown Visitors Center is just one of the places to see in Shepherdstown, so why not enjoy the other things to explore during your travels? Amble around the area's riverfront, or seek out its horseback riding.

Shepherdstown Visitors Center
Image for Shepherdstown Opera House

Shepherdstown Opera House

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.

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