Shady Side Vacations

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Find the Best Shady Side Vacation Packages

Shady Side Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩141,538 per night from Aug 18 to Aug 19
₩141,538
₩208,849 total
Aug 18 - Aug 19
includes taxes & fees
8.8/10 Excellent! (1,816 reviews)
"Excellent location for downtown and Acadamy access. Really enjoyed the history of the location and the displays. Staff was wonderful!"

Reviewed on Aug 7, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩223,106 per night from Sep 2 to Sep 3
₩223,106
₩254,341 total
Sep 2 - Sep 3
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Beautiful hotel in a great location!"

Reviewed on Aug 10, 2025

Graduate by Hilton Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is ₩118,740 per night from Sep 2 to Sep 3
₩118,740
₩135,572 total
Sep 2 - Sep 3
includes taxes & fees
5.8/10 (1,841 reviews)
"Close to DC City. The elevator is not in a good condition."

Reviewed on Aug 10, 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
See all 1,190 properties in Shady Side
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.

Discover the most popular places to visit in Shady Side

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Shadyside Park

Frequently asked questions

How much does a Shady Side vacation package cost?
You can pick up a vacation package to this destination on Expedia. But how much your vacation to Shady Side costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Shady Side?
To score cheap Shady Side vacation packages, plan your trip outside of peak periods like public holidays and major festivals. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Shady Side?
Generally, a few days is great for a Shady Side vacation. With a well-organized schedule, you can visit all the top sights including Shadyside Park, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Shady Side?
During your Shady Side vacation, you can count on experiencing some excellent watersports and fishing. Leave enough room in your itinerary to visit major attractions like Captain Avery Museum and Shadyside Park.
How to find the best Shady Side package deals?
Use Expedia's filters to find some of the best Shady Side package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Shady Side package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Shady Side vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Shady Side vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Shady Side?
If you have your Shady Side travel dates locked in, book as soon as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Shady Side?

  1. Choose when to travel: Check your calendar and pack your bags. Your favorite time of year and the available activities will also help you decide when to escape to Shady Side.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Shady Side. Then, select a property that matches your budget, whether that's an affordable stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Shady Side. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, lock in the perfect Shady Side vacation package for you.

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