Shady Side Vacations from $887

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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 Dupont Circle Hotel

The Dupont Circle Hotel

4.5 out of 5
Northwest
Save 100% on your flight
Price was $1,252, price is now $887 per person
$887
per person
Apr 29 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.4/10 Exceptional! (1,919 reviews)
Agent at desk was very polite...hotel is beautiful,quiet,excellent location...loved it

Reviewed on Mar 18, 2026

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
Price was $3,990, price is now $2,615 per person
$2,615
per person
May 31 - Jun 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (201 reviews)
My stay at the Rosewood Hotel was absolutely wonderful from start to finish. The level of service, attention to detail, and overall atmosphere made it a truly memorable experience. From the moment I arrived, the staff was warm, welcoming, and genuinely attentive. Check‑in was smooth and effortless, and I immediately felt like a valued guest. The room was beautifully designed—spacious, spotless, and thoughtfully arranged with luxurious touches throughout. The bed was incredibly comfortable, and the overall ambiance made it easy to relax. The hotel’s amenities were equally impressive. Whether enjoying the dining options, unwinding in the lounge areas, or simply taking in the elegant décor, everything felt refined and well-curated. Every interaction with the staff felt sincere, and the service consistently exceeded my expectations. Overall, my stay at the Rosewood was exceptional. I would highly recommend this hotel to anyone looking for comfort, luxury, and top‑tier hospitality. I’m already looking forward to returning!

Reviewed on Feb 19, 2026

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $1,471, price is now $989 per person
$989
per person
Jun 13 - Jun 19
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,340 reviews)
Loved this hotel! I would definitely stay here again. The only complaint I have, is the lighting in the room. The light over the headboard wasn’t too bright. Overall, I enjoyed my stay. The hotel was nice and spotless, the staff were very friendly. Not to mention, it is close to Union Station.

Reviewed on Mar 22, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,885, price is now $1,285 per person
$1,285
per person
May 31 - Jun 7
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,427 reviews)
Exceeded expectations!!

Reviewed on Mar 17, 2026

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $1,458, price is now $1,015 per person
$1,015
per person
Jun 13 - Jun 19
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9/10 Wonderful! (1,027 reviews)
I had an excellent overnight stay. The door man and front desk staff were friendly, the check in process was easy, the hotel is clean and well maintained and the room was very clean and comfortable. The shower felt amazing! The food and bartenders were great for both lunch and dinner. I had to leave the evening bartenders a nice tip because they were super friendly and engaging to me as someone traveling alone for a conference in another hotel. I accidentally left my toothbrush home (go figure!) and they gave me a complimentary one, toothpaste and extra water. I was well cared for and would recommend this hotel to everyone!

Reviewed on Mar 22, 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

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court Upper Marlboro MD
$106 nightly
The price is $120 total per night from Apr 5 to Apr 6
$120 total
Apr 5 - Apr 6
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
Friendly staff. Quiet. Clean. Great area!

Reviewed on Mar 23, 2026

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
$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! (1,001 reviews)
The toilet ran every few minutes. Some of the carpet as we entered the room was worn away.

Reviewed on Mar 22, 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
$114 nightly
The price is $130 total per night from Mar 31 to Apr 1
$130 total
Mar 31 - Apr 1
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
It was OK. Staff in general were not friendly or informative. The breakfast staff were very friendly and helpful. The pool is half the size it seems from the site. Great gym. Nothing was mentioned about the hot tub being out or the loud events that would be taking place that evening. It is a party ...

Reviewed on Mar 23, 2026

Crowne Plaza Annapolis by IHG
See all 1,171 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 $887 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.