Shady Side Vacations from $412

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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 LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Save 100% on your flight
Price was $621, price is now $412 per person
$412
per person
Apr 4 - Apr 8
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,008 reviews)
Friendly staff, great location and in hotel bar. Would definitely go back!

Reviewed on Jan 4, 2026

SIXTY DC

SIXTY DC

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $833, price is now $501 per person
$501
per person
Feb 14 - Feb 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (76 reviews)
Absolutely LOVED the stay!! Johnny was amazing forgot her name but the head of house keeping was amazing!! Best New Years yet!! Planning on coming back for a staycation with the wife where we can just unplug and relax. Just an overall amazing experience.

Reviewed on Jan 6, 2026

Hotel Indigo Old Town Alexandria by IHG

Hotel Indigo Old Town Alexandria by IHG

4 out of 5
Old Town Alexandria
Save 100% on your flight
Price was $753, price is now $508 per person
$508
per person
Apr 2 - Apr 6
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,000 reviews)
Had a great stay. Like the location and how easy it was to walk to nearby shops and restaurants. Parking was easy and secure. A great place for my family and I to stay for a few days.

Reviewed on Dec 27, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $679, price is now $464 per person
$464
per person
Mar 21 - Mar 23
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Staff is great. We love this hotel because it has plenty of self parking, so not having to wait for the valet to get your car every time saves a ton of time. The hotel is within the Gallaudet campus which is beautiful and feels very safe. The only issue we had were with the room itself. The furniture and fixtures are a bit dated/worn, though the beds are very comfortable. The sink drain was frozen in the bathroom, the toilet flusher was stuck. We managed to get around these things since we were only there one night and it would not deter us from coming again.

Reviewed on Dec 11, 2025

Cambria Hotel Washington D.C. Navy Yard Riverfront

Cambria Hotel Washington D.C. Navy Yard Riverfront

3 out of 5
Southwest
Save 100% on your flight
Price was $793, price is now $554 per person
$554
per person
Mar 11 - Mar 15
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,167 reviews)
It was good. Valet was okay.

Reviewed on Dec 3, 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 Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $86 total per night from Feb 8 to Feb 9
$86 total
Feb 8 - Feb 9
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Staff was amazing!!! The place was clean!!! Bathroom was out dated and had a couple holes in the ceiling by the fan. Pillows were tiny, that was probably my biggest issue. Had a restaurant inside, didn’t stop in during the evening. Had breakfast, price was reasonable. Got the buffet, food was ...

Reviewed on Jan 6, 2026

DoubleTree by Hilton Hotel 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
$92 nightly
The price is $104 total per night from Jan 22 to Jan 23
$104 total
Jan 22 - Jan 23
Total with taxes and fees
8/10 Very Good! (1,005 reviews)
Yes

Reviewed on Dec 30, 2025

DoubleTree by Hilton Hotel Largo/Washington DC
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $166 total per night from Jan 18 to Jan 19
$166 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on Dec 30, 2025

Graduate by Hilton Annapolis
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 $412 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.