Shady Side Holidays

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Top hotels in Shady Side

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
9.6/10 Exceptional! (21 reviews)
Nice Get Away
"Cute cottage in quiet neighborhood for a get away to the Eastern shore. Description is accurate and Mary was easy to communicate with. We enjoyed our stay."

Reviewed on 22 Jun 2025

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Bay views with kayaks, bikes, fire pit, crabbing and more
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
9.4/10 Exceptional! (3 reviews)
Military Bowl
"Wonderful place"

Reviewed on 29 Dec 2024

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Calloway Drive Retreat | House in Shady Side
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Shady Side
The price is €418 per night from 9 Aug to 10 Aug
€418
9 Aug - 10 Aug
includes taxes & fees
Hidden Treasure
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home"

Reviewed on 24 Jun 2025

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
See all 1,190 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.