Shady Side Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Shady Side Holiday
Our pick of the best Shady Side Hotel Deals
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
Shady Side MD
9.4/10 Exceptional! (8 reviews)
Beautiful Cottage
"We stayed here while my son went to summer camp at USNA and enjoyed the peaceful neighborhood. A couple hiccups occurred at the beginning of the trip but Charles was very open to resolving them with open and timely communication. The kids LOVED having the bikes to ride around the neighborhood and ..."
Reviewed on 19 June 2026
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
9.6/10 Exceptional! (37 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
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
NZ$189
13 Sept - 14 Sept
includes taxes & fees
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.
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.
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?
- 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.
- 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.
- 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.
- 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.
