Shepherdstown Vacations from SAR4,142

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Shepherdstown Vacation Packages

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 SAR4,880, price is now SAR4,142 per person
SAR4,142
per person
Sep 27 - Sep 30
found 21 hours ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Overall it was a good stay the room was clean.The staff was good in the beginning but at checkout the women working the front desk was rude and acted as if she didnā€™t want to be ask questions about the shuttles. And there was a problem with the printer I assume because I never received my receipt and she said she would email it .

Reviewed on 13 July 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Price was SAR5,727, price is now SAR4,823 per person
SAR4,823
per person
Sep 27 - Sep 30
found 21 hours ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (2,206 reviews)

The Poppy Georgetown

The Poppy Georgetown

4 out of 5
Northwest
Price was SAR6,379, price is now SAR5,465 per person
SAR5,465
per person
Sep 27 - Sep 30
found 21 hours ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (587 reviews)

The River Inn

The River Inn

4 out of 5
Northwest
Price was SAR5,350, price is now SAR4,677 per person
SAR4,677
per person
Sep 27 - Sep 30
found 21 hours ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (2,011 reviews)

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was SAR5,658, price is now SAR5,038 per person
SAR5,038
per person
Sep 27 - Sep 30
found 21 hours ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
Y

Reviewed on 16 July 2026

Find the Best Shepherdstown Vacation Packages

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 SARĀ 358 per night from Aug 16 to Aug 17
SARĀ 358
SARĀ 400 total
16 Aug - 17 Aug
includes taxes & fees
8/10 Very Good! (270 reviews)
"šŸ‘"

Reviewed on 17 July 2026

Quality Inn Shepherdstown
ā¤ļø Secluded 1940s Romantic Tiny House on the River

ā¤ļø Secluded 1940s Romantic Tiny House on the River

Shepherdstown WV
The price is SARĀ 253 per night from Jul 29 to Jul 30
SARĀ 253
SARĀ 511 total
29 Jul - 30 Jul
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 13 June 2026

ā¤ļø 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 SARĀ 378 per night from Aug 10 to Aug 11
SARĀ 378
SARĀ 424 total
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,294 reviews)
"Staff was very friendly. Room was as clean but dated. Carpet was old and walls needed some fresh paint. Room was kinda dark could use some better lighting. Good location off highway and good options"

Reviewed on 16 July 2026

Country Inn & Suites by Radisson, Hagerstown, MD
See all 965 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.

Stay near popular Shepherdstown attractions

Shepherdstown Opera House

10.0/10 (1 review)
This intimate historic theater 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.
See properties

Frequently asked questions

How much does a Shepherdstown vacation package cost?
You'll find cheap prices from SAR4,142 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 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 traveling 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.