Shady Side Vacations from $283
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The Latest Shady Side Vacation Packages
- The Westin DC Downtown
Oct 9 - Oct 11The Westin DC Downtown + Flight
Downtown Washington D.C.2 nights4.0 star property8.8/10 - Excellent (1,011 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Kellogg Conference Hotel at Gallaudet University
Oct 22 - Oct 25Kellogg Conference Hotel at Gallaudet University + Flight
Northeast3 nights3.0 star property8.4/10 - Very Good (1,007 reviews)"I love that it’s located on university campus, great for family bringing students from out of state."Reviewed August 5, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Hotel Burg
Oct 2 - Oct 5Hotel Burg + Flight
Leesburg's Old and Historic District3 nights4.0 star property9.6/10 - Exceptional (105 reviews)"Excellent service and hospitality. Beautiful and clean. Would come back here many times. Friendly and professional staff. It was a great experience."Reviewed August 4, 2026Roundtrip • Boston (BOS) - Baltimore (BWI)BOS - BWI • Nonstop BWI - BOS • Nonstop - Furnished Apartments
Sep 9 - Sep 14Furnished Apartments + Flight
Ashton Heights5 nights3.0 star property9.0/10 - Wonderful (4 reviews)"Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows. Host was helpful and able to accommodate my schedule needs too. "Reviewed April 1, 2025Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Phoenix Park Hotel
Oct 7 - Oct 10Phoenix Park Hotel + Flight
Northwest3 nights3.5 star property9.4/10 - Exceptional (2,169 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop
Shady Side Hotel Deals
"My mother-in-law had accessibility needs, and the staff were incredibly helpful and responsive in getting her the type of room and service she needed."
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis"👍"
Hampton Inn & Suites Glenarden/Washington DC
Hampton Inn & Suites Glenarden/Washington DC"Everything was great!"
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD"We thoroughly enjoyed both the breakfast and breakfast area. The hotel was kept in very nice & clean order. The personnel were, for the most part, helpful."
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
"Nice very well location"
Frequently Asked Questions
How much does a Shady Side vacation package cost?
You can pick up a vacation package to this destination from $283 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.