Shady Side Vacations from $342
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The Latest Shady Side Vacation Packages
- Lord Baltimore Hotel
Oct 1 - Oct 4Lord Baltimore Hotel + Flight
Downtown Baltimore3 nights3.5 star property8.4/10 - Very Good (3,107 reviews)"Black mold in shower And elevators can be hectic especially at check out times"Reviewed July 29, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - The Poppy Georgetown
Oct 14 - Oct 20The Poppy Georgetown + Flight
Northwest6 nights4.0 star property9.4/10 - Exceptional (589 reviews)Roundtrip • Dallas (DFW) - Baltimore (BWI)DFW - BWI • Nonstop BWI - DFW • Nonstop$3,016$1,684found 1 day agoper traveler - Hotel Burg
Oct 2 - Oct 5Hotel Burg + Flight
Leesburg's Old and Historic District3 nights4.0 star property9.6/10 - Exceptional (100 reviews)Roundtrip • Boston (BOS) - Baltimore (BWI)BOS - BWI • Nonstop BWI - BOS • Nonstop - Phoenix Park Hotel
Sep 17 - Sep 22Phoenix Park Hotel + Flight
Northwest5 nights3.5 star property9.4/10 - Exceptional (2,170 reviews)"The best hotel I ever stayed. I want to come back whenever I travel to DC again. It's so convenient to get train station. Recommended to my friends."Reviewed July 28, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Sandaway Suites & Beach
Sep 13 - Sep 17Sandaway Suites & Beach + Flight
Oxford3 nights3.0 star property9.4/10 - Exceptional (188 reviews)"This is an extraordinary place to come and experience tranquility at its best! The view evokes peace of mind. The owners are very much hands on- making sure their guests feel pampered and filled with joy! They have a unique quality that no other owners, to my knowledge have exhibited. And that is such an amazing spirit of generosity. You’re given bagfuls of treats and a lovely local piece of artwork. Then you’re given a basketful of treats and gourmet coffee for breakfast. This is by far one..."Reviewed July 24, 2026Roundtrip • Los Angeles (LAX) - Baltimore (BWI)LAX - PHL • 1 stop PHL - LAX • 1 stop$734$504found 12 hours agoper traveler
Shady Side Hotel Deals
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGFrequently Asked Questions
How much does a Shady Side vacation package cost?
You can pick up a vacation package to this destination from $342 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.