A river with boats, a marina, and a town with houses and buildings.

Shady Side Vacations from $352

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The Latest Shady Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 4 - Oct 7

    Eurostars Saint Gregory Dupont Circle Georgetown + Flight

    Downtown Washington D.C.
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,000 reviews)
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - IADNonstop IAD - ATLNonstop
    Save 100% on your flight
    $555
    $352
    per traveler
    found 1 day ago
    Eurostars Saint Gregory Dupont Circle Georgetown
  • Oct 9 - Oct 14

    Kellogg Conference Hotel at Gallaudet University + Flight

    Northeast
    5 nights
    3.0 star property
    8.2/10 - Very Good (1,000 reviews)
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - BWINonstop BWI - ATLNonstop
    Save 100% on your flight
    $962
    $531
    per traveler
    found 1 day ago
    Kellogg Conference Hotel at Gallaudet University
  • Oct 2 - Oct 5

    Hotel Burg + Flight

    Leesburg's Old and Historic District
    3 nights
    4.0 star property
    9.6/10 - Exceptional (100 reviews)
    Roundtrip Boston (BOS) - Baltimore (BWI)
    BOS - BWINonstop BWI - BOSNonstop
    Save 100% on your flight
    $1,617
    $1,019
    per traveler
    found 1 day ago
    Hotel Burg
  • Oct 4 - Oct 7

    Hotel Washington + Flight

    Downtown Washington D.C.
    3 nights
    5.0 star property
    9.0/10 - Wonderful (2,454 reviews)
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - IADNonstop IAD - ATLNonstop
    Save 100% on your flight
    $834
    $531
    per traveler
    found 1 day ago
    Hotel Washington
  • Sep 24 - Sep 28

    Sheraton Baltimore North Hotel + Flight

    Towson
    4 nights
    3.5 star property
    8.4/10 - Very Good (1,002 reviews)
    "No brainer, stay here! You will not be dissapointed!"
    Reviewed July 30, 2026
    Roundtrip Atlanta (ATL) - Baltimore (BWI)
    ATL - IADNonstop IAD - ATLNonstop
    Save 100% on your flight
    $541
    $372
    per traveler
    found 1 day ago
    Sheraton Baltimore North Hotel

Shady Side Hotel Deals

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.

Frequently Asked Questions

How much does a Shady Side vacation package cost?

You can pick up a vacation package to this destination from $352 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?

You can generally find reduced prices and better availability in November, December and January. Take a look at our cheap Shady Side vacation packages and you could score some great off-season discounts.

How many days is enough for Shady Side?

The ideal duration for your Shady Side vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to check out all the top sights and discover some hidden gems along the way.

Is it worth booking a vacation package to Shady Side?

Whether you're planning to visit attractions like Shadyside Park and Captain Avery Museum, or want to experience its top-notch fishing and watersports, a Shady Side vacation will leave you with lasting memories. Book your getaway with Expedia and discover why Shady Side is such a good vacation destination.

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.

Does Expedia offer Book Now, Pay Later Shady Side vacation packages?

If you're like us, you love going away but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Shady Side break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.

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