Shady Side Vacations from $175

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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.
Hilton Garden Inn Washington DC/U.S. Capitol

Hilton Garden Inn Washington DC/U.S. Capitol

3 out of 5
Northeast
Save 100% on your flight
Price was $271, price is now $175 per person
$175
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (1,621 reviews)
Front desk are nice and helpful as well as the valet parking people.

Reviewed on Oct 8, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was $1,305, price is now $610 per person
$610
per person
Nov 17 - Nov 23
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.8/10 Exceptional! (55 reviews)
The hotel is very chic and comfortable. The staff especially Amna at the reception was so sweet and helpful. The location is perfect - just in the heart of DuPont.circle.

Reviewed on Oct 2, 2025

Hilton Alexandria Old Town

Hilton Alexandria Old Town

4 out of 5
Old Town Alexandria
Save 100% on your flight
Price was $629, price is now $374 per person
$374
per person
Dec 16 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Room was nice, staff was incredible

Reviewed on Oct 7, 2025

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $386, price is now $263 per person
$263
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (36 reviews)
I had a great stay! The room was very clean and comfortable, and the staff were incredibly kind and helpful throughout my visit. Their friendly attitude made the experience even better. I’d definitely stay here again and recommend it to others.

Reviewed on Oct 8, 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

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
$145 nightly
The price is $166 total per night from Nov 2 to Nov 3
$166 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,835 reviews)
"Beautiful hotel in the heart of Annapolis. Lots of charm"

Reviewed on Oct 3, 2025

Historic Inns of Annapolis
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
$94 nightly
The price is $107 total per night from Nov 3 to Nov 4
$107 total
Nov 3 - Nov 4
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
"Customer Service was excellent."

Reviewed on Sep 29, 2025

DoubleTree by Hilton Hotel Largo/Washington DC
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
$85 nightly
The price is $96 total per night from Oct 26 to Oct 27
$96 total
Oct 26 - Oct 27
Total with taxes and fees
5.8/10 (1,886 reviews)
Great place for a stay near DCA
"Great place to stay and very helpful and approachable staff. The only downside was that the exercise room was undergoing remodeling and there was a very limited number of exercise machines."

Reviewed on Sep 23, 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
See all 1,218 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.

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 $175 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.