Shady Side Vacations from $296

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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.
Studio 6 Springfield, Va – Washington Dc Southwest

Studio 6 Springfield, Va – Washington Dc Southwest

2 out of 5
Price was $381, price is now $296 per person
$296
per person
Nov 7 - Nov 11
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
7.8/10 Good! (135 reviews)
Kitchen was a plus, lack of pots pans dishes and utensils were a minus.

Reviewed on Aug 11, 2025

The Westin Tysons Corner

The Westin Tysons Corner

4 out of 5
Price was $398, price is now $333 per person
$333
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
The room was very clean, well organized, and, oddly enough, I really like the placement of the furnitures. The parking lot method was the only downside. Having to go only and use a third party to gain access to parking made things a bit less convenient.

Reviewed on Aug 18, 2025

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

2.5 out of 5
Price was $746, price is now $632 per person
$632
per person
Oct 3 - Oct 10
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Washington (DCA)
7.8/10 Good! (1,001 reviews)
I was very happy with my stay here. They had a friendly and efficient staff and clean rooms. The hot breakfast was good and there were some nice options to choose from. I will reserve here again next time I’m in the area!

Reviewed on Aug 19, 2025

Washington Dulles Marriott Suites

Washington Dulles Marriott Suites

3.5 out of 5
Save 100% on your flight
Price was $741, price is now $630 per person
$630
per person
Oct 10 - Oct 14
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (984 reviews)
what a great option near IAD. clean with super comfortable beds and very spacious suites. Would definitely recommend and would definitely stay here again.

Reviewed on Aug 16, 2025

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 out of 5
Price was $352, price is now $301 per person
$301
per person
Oct 11 - Oct 13
just found
Roundtrip flight included
Charlotte (CLT) to Washington (DCA)
9.4/10 Exceptional! (440 reviews)
There was a food truck, outdoor, covered bar and live music. The bar area and music ended early. Great atmosphere.

Reviewed on Jul 5, 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

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 Sep 8 to Sep 9
$163 total
Sep 8 - Sep 9
Total with taxes and fees
8.8/10 Excellent! (1,836 reviews)
"There were no ghosts!"

Reviewed on Aug 20, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $183 total per night from Sep 2 to Sep 3
$183 total
Sep 2 - Sep 3
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
"Very good"

Reviewed on Aug 20, 2025

Graduate by Hilton Annapolis
See all 1,203 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 $296 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.