Shady Side Vacation Packages

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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.

Top Shady Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
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
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
Wish there was coffee in the lobby at all times

Reviewed on Jul. 8, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
Great staff. Nice rooms. Would stay here again.

Reviewed on Jul. 8, 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Sep 5 - Sep 8
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (2,488 reviews)
I had a corner room with city view over 4th of July weekend to be able to see the fireworks. That was the nice part. What bothered me is that neighbors in the residences next to the hotel can see right into the hotel room if your shades are open. One of the windows had no room darkening shades which was miserable for me being on California time & waking up with the sun. Paid parking on the G2 level underground lot isn't ideal but at least there's guaranteed parking. I won't stay there again.

Reviewed on Jul. 10, 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
9.2/10 Wonderful! (621 reviews)
The hotel is excellent overall but the decision to use the hotel for extracurricular activities while restricting the guests while those activities are going on is not good at all.

Reviewed on Jul. 12, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 14 - Sep 21
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9/10 Wonderful! (1,851 reviews)
Everyone was great, then staff was amazing. The only issue we had was the TEXT System for room service was not good at all. We tried to us it 4 times and it did not work at all. The entire staff was amazing. We has a credit for the room service but was not aware. Once I brought it to the attention of the floor manager. I totally spaced on her name. She was blonde, wore a flowery blouse and had on khaki pants. Was super helpful. The front desk staff was also great, I had many of them help me out but Terri and Elvis were the names that stood out.

Reviewed on Jul. 9, 2025

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Shady Side Hotel Deals

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
The price is CA $140 per night from Jul 20 to Jul 21
CA $140
CA $206 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (1,802 reviews)
"Our stay was fabulous! I loved the scent as you walked through the lobby door, I loved the historical components, all of the staff were super friendly, and I loved how close it was to walk downtown and by the dock."

Reviewed on Jul. 11, 2025

Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
3 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 20 to Jul 21
CA $129
CA $148 total
Jul 20 - Jul 21
includes taxes & fees
6/10 (1,781 reviews)
"It's always amazing when I stay at this property."

Reviewed on Jul. 10, 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Comfort Inn Largo-Washington DC East
Comfort Inn Largo-Washington DC East
3 out of 5
9421 Largo Drive West, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 20 to Jul 21
CA $122
CA $138 total
Jul 20 - Jul 21
includes taxes & fees
7.4/10 Good! (96 reviews)
"It was a fine place to stay"

Reviewed on Jul. 11, 2025

Comfort Inn Largo-Washington DC East
See all 1,180 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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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

Frequently asked questions

How much does a Shady Side vacation package cost?
You can pick up a vacation package to this destination from CA $464 on Expedia. However, how much your vacation to Shady Side costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Shady Side?
The off-season is the best time to visit Shady Side if you're on a budget. Another tip for scoring cheap Shady Side vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Shady Side?
We'd recommend booking a Shady Side vacation for a minimum of 3 days. This will give you enough time to check off major attractions such as Captain Avery Museum and Franklin Point State Park, and also explore neighbourhoods like Cape Anne and Deale Beach. You could even make time for one or two day trips beyond Shady Side.
Is it worth booking a vacation package to Shady Side?
During your Shady Side vacation, you can look forward to enjoying some excellent watersports and fishing. Leave enough room in your itinerary to discover leading sights like Captain Avery Museum and Shadyside Park.
How to find the best Shady Side package deals?
Use Expedia's handy filters to find some tempting 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 search for Shady Side package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Shady Side vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can customize your Shady Side getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Shady Side?
If you have your Shady Side travel dates finalized, book as early as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Shady Side?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Shady Side.
  2. Plan your budget wisely: In addition to the cost of your accommodations, you should factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Shady Side.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to get to in Shady Side. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the ideal Shady Side vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.