Shady Side Packages (Flight + Hotel)

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Top hotels 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
8.8/10 Excellent! (1,824 reviews)
"I really liked the hotel and staff. The only thing I didnt like was they had a convention there that I was unaware of and we were unable to get breakfast or enjoy the restaurant area. Other than that very nice!"

Reviewed on 14 Aug 2025

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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
The price is ฿5,217 per night from 2 Sept to 3 Sept
฿5,217
฿5,947 total
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Beautiful hotel in a great location!"

Reviewed on 10 Aug 2025

Graduate by Hilton 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 ฿2,763 per night from 2 Sept to 3 Sept
฿2,763
฿3,154 total
2 Sept - 3 Sept
includes taxes & fees
5.8/10 (1,850 reviews)
"I will absolutely go again to this beautiful place/hotel thank you"

Reviewed on 12 Aug 2025

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
See all 1,188 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.

Frequently asked questions

How much does a Shady Side holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday 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?
To score cheap Shady Side holiday packages, plan your trip outside of peak periods like public holidays and major festivals. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Shady Side?
Generally, a few days is great for a Shady Side holiday. With a well-organised schedule, you can visit all the top sights including Shadyside Park, as well as discover some hidden gems along the way.
Is it worth booking a holiday package to Shady Side?
During your Shady Side holiday, you can count on experiencing some excellent watersports and fishing. Leave enough room in your itinerary to visit major attractions like Captain Avery Museum and Shadyside Park.
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 holiday package well in advance.
Is it cheaper to book a Shady Side holiday as a package?
Expedia holiday 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 customised Shady Side holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Shady Side?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite time of year and the available activities will also help you decide when to escape to Shady Side.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to put aside for your trip to Shady Side. Then, select a property that matches your budget, whether that's an affordable stay or a more upscale getaway.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to experience in Shady Side. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your travel dates and duration, lock in the perfect Shady Side holiday package for you.

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