Shady Side Holidays from AU$2,309

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Your Shady Side Holiday

Simplify your travel planning with a Shady Side holiday package. A great neighbourhood to base yourself in this fascinating city is Historic District, which is good for history and plenty more. Make your trip to Shady Side even more enjoyable by including some sightseeing. Triton Beach, Shadyside Park and Smithsonian Environmental Research Centre are some of the popular attractions you'll want to explore. Your ultimate Shady Side holiday is just clicks away. Explore accommodation, flights and more on Expedia for an adventure that's tailored to suit your style.

The Latest Shady Side Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (2,560 reviews)
Beautiful room with great proximity to The White House

Reviewed on 1 Aug. 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
10/10 Exceptional! (12 reviews)
Very nice and clean hotel, very friendly team, neat and impressive technology equipped rooms, I would highly recommend it to friends and family

Reviewed on 25 Jul. 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (1,607 reviews)
Very well maintained

Reviewed on 2 Aug. 2025

Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (2,020 reviews)
Beautiful grounds, loved the gardens! Walkable to good dining. Pool is open till late. Would stay again if in the area.

Reviewed on 2 Aug. 2025

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
9.4/10 Exceptional! (1,464 reviews)
Everything from check in, out, and valet was great.

Reviewed on 31 Jul. 2025

Shady Side Holiday

Shady Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
5,800
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Chesapeake Beach Water Park, Bayside History Museum and Thanksgiving Farm Wines

Our pick of the best Shady Side Hotel Deals

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

Get rates
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

Get rates
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 AU$739 per night from 4 Aug to 5 Aug
AU$739
4 Aug - 5 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 1,187 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Shady Side holiday package cost?
You can pick up a holiday package to this destination from AU$2,309 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.