Shady Side Vacations from $263

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Your Shady Side Vacation

Take the stress out of travel planning by booking a Shady Side vacation package. One of the best neighborhoods to base yourself in this vibrant city is Deale Beach, which is good for walking and a lot more. Shadyside Park, Franklin Point State Park and Galesville Heritage Museum are just some of the attractions you'll want to explore during your trip to Shady Side. That dream Shady Side vacation is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

The Latest Shady Side vacation packages

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,821 reviews)
I really enjoyed staying at a smaller hotel with charm! The staff is so nice and the location is great. Would stay here again.

Reviewed on Aug 16, 2025

Hilton McLean Tysons Corner

Hilton McLean Tysons Corner

4 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,001 reviews)
This was the nicest Hilton I have stayed at and the price was great

Reviewed on Aug 8, 2025

Hilton Garden Inn Reagan National Airport

Hilton Garden Inn Reagan National Airport

3.5 out of 5
Crystal City
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,694 reviews)
Very convenient, good for travelers

Reviewed on Aug 14, 2025

Embassy Suites by Hilton Tysons Corner

Embassy Suites by Hilton Tysons Corner

3.5 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (2,691 reviews)
Thought parking was free

Reviewed on Aug 17, 2025

Landing Washington DC near Washington Navy Yard

Landing Washington DC near Washington Navy Yard

2 out of 5
Southeast
per person
Sep 17 - Sep 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
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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

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Captain Avery Museum

Shady Side Hotel Deals

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
9.6/10 Exceptional! (21 reviews)
Nice Get Away
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."

Reviewed on Jun 22, 2025

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Bay views with kayaks, bikes, fire pit, crabbing and more
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
9.4/10 Exceptional! (3 reviews)
Military Bowl
"Wonderful place"

Reviewed on Dec 29, 2024

Get rates
Calloway Drive Retreat | House in Shady Side
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
$143 nightly
The price is $163 total per night from Aug 25 to Aug 26
$163 total
Aug 25 - Aug 26
Total includes taxes and fees
8.8/10 Excellent! (1,823 reviews)
"Lovely room. Comfortable bed."

Reviewed on Aug 13, 2025

Historic Inns of Annapolis
See all 1,194 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.

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Frequently asked questions

How much does a Shady Side vacation package cost?
You can pick up a vacation package to this destination from $263 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.