Shady Side Holidays

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    Packages with flights are ATOL protected

Your Shady Side Holiday

Take the stress out of travel planning by booking a Shady Side holiday package. One of the best neighbourhoods to base yourself in this vibrant city is Deale Beach, which is good for walking and a lot more. Shadyside Park, Franklin Point State Park and Galesville Heritage Museum are just some of the attractions you'll want to explore during your trip to Shady Side. That dream Shady Side holiday is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

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, Matapeake State Park and Triton Beach

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! (45 reviews)
"This property was clean, comfortable, and offered all the little touches that made it feel like home. We loved the neighborhood and backyard and enjoyed walking and exploring the area. We hosted our Midshipman and a couple of her friends for her birthday and they loved relaxing at this house and ..."

Reviewed on 5 Nov 2026

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Lovely bay views with kayaks, bikes, fire pit, crabbing & more
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 £73 per night from 26 Nov to 27 Nov
£73
26 Nov - 27 Nov
includes taxes & fees
6.2/10 (2,001 reviews)
"N/A"

Reviewed on 14 Nov 2026

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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
The price is £87 per night from 23 Nov to 24 Nov
£87
23 Nov - 24 Nov
includes taxes & fees
9/10 Wonderful! (2,072 reviews)
"Positives included being close to the sites and Annapolis history, a very attentive hotel and valet parking staff with quick response to requests. Negatives included a noisy refrigerator, no microwave and a restaurant nearby playing loud music into the late evening. The only real choice was using ..."

Reviewed on 14 Nov 2026

Historic Inns of Annapolis
See all 1,215 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
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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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Frequently asked questions

How much does a Shady Side travel package cost?
The most affordable Shady Side travel package is , so the trip of your dreams can become a reality — without the high price tag. Combine flights, hotels and car rentals to customize a package that fits you.
If I'm not able to travel, can I cancel my Shady Side travel package?
Certainly, and we'll help you every step of the way. You may be able to change or cancel your Shady Side travel package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your circumstances unexpectedly change, visit our Customer Service Portal for more information.
How do I get a cheap travel package to Shady Side?
Our Shady Side travel packages mean plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and tours into a budget-friendly package. But cheap prices are just the beginning of your next big adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties throughout the world to pick from. No matter your budget, there's a travel package that's perfect for you.
Does Expedia offer Book Now, Pay Later Shady Side holidays?
Expedia has teamed up with online lender Klarna to make booking your next break a little easier on the wallet. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd like to pay for your getaway in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Shady Side?
With interesting attractions like Shadyside Park and Captain Avery Museum in this area, look for a hotel situated near either of them. Galesville Heritage Museum is another Shady Side sight that draws in the crowds.
What are the top hotels in Shady Side?
Book a stay at Renaissance Baltimore Harborplace Hotel. It's one of this area's most sought-after properties. Another top-rated option in Shady Side is Hyatt Regency Baltimore Inner Harbour.
How far in advance should I book my Shady Side holiday?
Travellers can normally browse international airfares on Expedia within 12 months of the departure date. Booking at the last minute? With a stroke of luck, it's still possible to score an affordable ticket only weeks before your journey.
What does an Expedia Shady Side travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply mix and match your favourite bundle and gain access to great discounts. Once you've made your booking, add on a few tours and experiences and watch your savings grow. When it comes to organising your Shady Side escape, you're in charge!
What should I know before booking a Shady Side travel package?
Locking in all the parts of your holiday together is a smart way to save. Bundle your airfares, rental cars and hotels into a convenient package. But you're not limited to hotels. Expedia has all sorts of properties, including holiday rentals such as beach villas and serviced residences. Your choices are almost endless!
Can I choose my airline with a Shady Side Expedia travel package?
You can, and with more than 550 airlines to choose from all over the world, you're not short on choice. Browse the available options and find out which airline best fits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.