Shady Side Vacations from $140

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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.
Home2 Suites By Hilton Ashburn, Va

Home2 Suites By Hilton Ashburn, Va

3 out of 5
Save 100% on your flight
Price was $258, price is now $140 per person
$140
per person
Jan 16 - Jan 19
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $653, price is now $284 per person
$284
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18.8/10 Exceptional! (1,005 reviews)
Everything was fantastic. Beautiful property.

Reviewed on Nov 10, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $688, price is now $356 per person
$356
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18/10 Exceptional! (1,084 reviews)
Room was spotless and comfortable and quiet. All staff were very friendly and helpful. Great location to walk to the Metro and restaurants and the White House!

Reviewed on Oct 28, 2025

SIXTY DC

SIXTY DC

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $427, price is now $228 per person
$228
per person
Feb 5 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
18.8/10 Exceptional! (76 reviews)
Room was clean, average amenities, great location, very nice in house restaurant with great cocktails.

Reviewed on Nov 17, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $770, price is now $430 per person
$430
per person
Feb 12 - Feb 15
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
18.4/10 Exceptional! (2,031 reviews)
This hotel was a great place to stay.

Reviewed on Nov 20, 2025

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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
$92 nightly
The price is $104 total per night from Dec 7 to Dec 8
$104 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Clean room, staff was wonderful, breakfast was great, room was comfortable temp wise to sleep.

Reviewed on Nov 22, 2025

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
$154 nightly
The price is $175 total per night from Nov 30 to Dec 1
$175 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (1,896 reviews)
.

Reviewed on Nov 18, 2025

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $70 total per night from Dec 21 to Dec 22
$70 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
Everything was great

Reviewed on Nov 19, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,169 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 $140 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.