Shady Side Vacations from $389

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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
Price was $561, price is now $389 per person
$389
per person
Apr 1 - Apr 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Staff was professional, helpful, and friendly!

Reviewed on Feb 16, 2026

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $832, price is now $534 per person
$534
per person
May 21 - May 26
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Great location! Room was small but bed very comfortable. Bathroom was a good size and clean. Would recommend!

Reviewed on Mar 1, 2026

Homewood Suites by Hilton Arlington Rosslyn Key Bridge

Homewood Suites by Hilton Arlington Rosslyn Key Bridge

3 out of 5
Rosslyn
Save 100% on your flight
Price was $935, price is now $655 per person
$655
per person
May 21 - May 26
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.4/10 Exceptional! (1,001 reviews)
clean room, friendly staff, good amenities

Reviewed on Mar 1, 2026

Hyatt Place Arlington/Courthouse Plaza

Hyatt Place Arlington/Courthouse Plaza

3 out of 5
Court House
Price was $607, price is now $439 per person
$439
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,004 reviews)
Room was clean… location is accessible… breakfast was really room and most of all its the staff !!! They are all fantastic!!! Superb

Reviewed on Mar 1, 2026

Elegant 2BR Apartment - Minutes to D.C.

Elegant 2BR Apartment - Minutes to D.C.

3.5 out of 5
Crystal City
Save 100% on your flight
Price was $1,338, price is now $972 per person
$972
per person
May 14 - May 17
found 6 hours ago
Roundtrip flight included
Minneapolis (MSP) to Washington (DCA)
9.8/10 Exceptional! (7 reviews)
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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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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

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court Upper Marlboro MD
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $120 total per night from Mar 15 to Mar 16
$120 total
Mar 15 - Mar 16
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
room had a smell, heater was loud, fridge leaned drastically to the right, hdmi cables on the tv didnt work

Reviewed on Feb 26, 2026

DoubleTree by Hilton Hotel Largo/Washington DC
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
$208 nightly
The price is $237 total per night from Mar 8 to Mar 9
$237 total
Mar 8 - Mar 9
Total with taxes and fees
9/10 Wonderful! (1,877 reviews)
Such a cool place to stay! Water pressure wasn’t great but it’s a very old building.

Reviewed on Feb 26, 2026

Historic Inns of 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
$81 nightly
The price is $91 total per night from Mar 10 to Mar 11
$91 total
Mar 10 - Mar 11
Total with taxes and fees
6/10 (1,989 reviews)
Clean up around the grounds full of dogs 💩 poo

Reviewed on Feb 26, 2026

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
See all 1,170 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.

Find the Best Shady Side Vacation Packages

Shady Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
5,800
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Chesapeake Beach Water Park, Matapeake State Park and Bayside History Museum

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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 $389 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.