Shady Side Holidays

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Top hotels in Shady Side

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
9.6/10 Exceptional! (38 reviews)
"This property was in a central location to lots of places. I did think there was going to be a larger beach that you could go to within the community, however it was a very enjoyable stay. The hostess was sweet and the house is adorable."

Reviewed on 9 Aug 2026

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Lovely bay views with kayaks, bikes, fire pit, crabbing & more
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
€95
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (1,133 reviews)
"My check-in went smoothly. I had a young lady assist me, and she was absolutely amazing! She was so sweet, funny, and welcoming. She was even kind enough to offer me two cookies and a bottle of water when I arrived at my room. I believe her name tag said Ms. Betty. She had beautiful red and orange ..."

Reviewed on 27 Aug 2026

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
€134
27 Sept - 28 Sept
includes taxes & fees
9/10 Wonderful! (1,973 reviews)
"My beef is with cancelation. I had to unexpectedly travel out of the country for a death on the family. So I called to let the hotel I was not coming and asked for a refund, after some discussion the hotel agreed not to charge. A couple days later I got an invoice copy from you guys, telling how ..."

Reviewed on 28 Aug 2026

Historic Inns of Annapolis
See all 1,208 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.

Stay near popular Shady Side attractions

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
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Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants.
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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.

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