Shady Side Vacations from $446

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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 $677, price is now $446 per person
$446
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,481, price is now $1,028 per person
$1,028
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (2,213 reviews)
Room was very nice and staff was excellent - super friendly and helpful.

Reviewed on Mar 5, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,051, price is now $736 per person
$736
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,416 reviews)
Everything was beautiful and everyone I encountered was so nice and helpful!

Reviewed on Mar 9, 2026

Hyatt Place Arlington/Courthouse Plaza

Hyatt Place Arlington/Courthouse Plaza

3 out of 5
Court House
Save 100% on your flight
Price was $1,289, price is now $907 per person
$907
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,062 reviews)
The location is unbeatable, near restaurants and right by the metro stop. We had the king room on a high floor which was nice and spacious, however the hvac system in the room is super loud! When it goes on it sounds like an engine is running in the room, even with earplugs we could hear it and it disrupted our sleep. Also, the bathroom sink faucet was loose and wobbly, every time you turned it on it felt like it was going to fall out. In addition, the shower water pressure is barely more than a trickle, but the water was hot. If you want an amazing location this is the place, but the hotel def needs some TLC.

Reviewed on Mar 9, 2026

Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,473, price is now $1,062 per person
$1,062
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,368 reviews)
Super easy check in experience. Friendly staff. Room was super well presented. Only issue was the fire alarm went off mid-stay for seemingly no reason. Shower also only got medium-warm and not really ever hot, but it was fine.

Reviewed on Mar 9, 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
$170 nightly
The price is $193 total per night from Mar 29 to Mar 30
$193 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
Lovely and fun theme hotel. Staff was wonderdul

Reviewed on Mar 8, 2026

Graduate by Hilton Annapolis
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 15 to Mar 16
$125 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
Clean, friendly staff and great area

Reviewed on Mar 11, 2026

Crowne Plaza Annapolis by IHG
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
$157 nightly
The price is $179 total per night from Apr 2 to Apr 3
$179 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (1,886 reviews)
Great location for walking around Annapolis

Reviewed on Mar 9, 2026

Historic Inns of Annapolis
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 $446 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.