Shady Side Vacations from $603

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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 Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $927, price is now $603 per person
$603
per person
Jun 8 - Jun 12
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.6/10 Excellent! (1,006 reviews)
I do not welcome pets into my home. When I travel, pets should be outside not inside where am. Each staff person was wonderful. The included breakfast and wine/cheese events are very enjoyable and why I choose Normandy! Thanks.

Reviewed on Mar 7, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $1,317, price is now $812 per person
$812
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.4/10 Exceptional! (1,066 reviews)
The proximity of the hotel to the Anthem is amazing! A one minute walk and lots of restaurants nearby. Lovely hotel and helpful staff.

Reviewed on Mar 6, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was $1,966, price is now $1,318 per person
$1,318
per person
May 17 - May 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.4/10 Exceptional! (1,418 reviews)
Experience overall was excellent

Reviewed on Mar 14, 2026

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
Price was $924, price is now $620 per person
$620
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,002 reviews)
Staff was professional, helpful, and friendly!

Reviewed on Feb 16, 2026

Hotel AKA Alexandria

Hotel AKA Alexandria

4 out of 5
Old Town North
Save 100% on your flight
Price was $1,001, price is now $679 per person
$679
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.6/10 Exceptional! (665 reviews)
The restaurant inside need a better selection of food. Close walk to other places to eat but overall my stay was good

Reviewed on Mar 12, 2026

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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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$171 nightly
The price is $195 total per night from Mar 29 to Mar 30
$195 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Central l9cation, easy walk to all sites.

Reviewed on Mar 12, 2026

Graduate by Hilton 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
$106 nightly
The price is $120 total per night from Mar 30 to Mar 31
$120 total
Mar 30 - Mar 31
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
It has become one of my favorite places to stay for business over the past few months. The good news is that they’re renovating, so the rooms now look modern with wood floors and removed popcorn ceilings. The bathroom is also slightly newer. I was pleased with the refresh. Rooms are always clean ...

Reviewed on Mar 15, 2026

DoubleTree by Hilton Hotel Largo/Washington DC
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
The price is $125 total per night from Mar 18 to Mar 19
$125 total
Mar 18 - Mar 19
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Clean comfortable room. 426 broken TPHolder. Broken H/C handle in the shower.

Reviewed on Mar 15, 2026

Crowne Plaza Annapolis by IHG
See all 1,184 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 $603 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.