Shady Side Holidays from £941

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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.

Top Shady Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on 3 Aug 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
14 Oct - 21 Oct
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
8.8/10 Excellent! (1,624 reviews)
Room is basic but good enough for a short stay if you’re not staying in much. Location is convenient. Service from the staff is lacking. Overall, really good value for the price.

Reviewed on 6 Aug 2025

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
14 Oct - 21 Oct
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
9.4/10 Exceptional! (1,437 reviews)
Service is excellent. Convenient location. Cute decor.

Reviewed on 8 Aug 2025

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
14 Oct - 21 Oct
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
8.8/10 Excellent! (2,579 reviews)
The staff was very helpful and courteous, offering details about the surrounding areas to explore. The hotel had a very pleasant clean scent throughout, which was nice. The bed and linens were very comfortable, with a very nice and larger than normal layout of the room. Great accomodations for the price.

Reviewed on 8 Aug 2025

The Dupont Circle Hotel

The Dupont Circle Hotel

4.5 out of 5
Northwest
Save 100% on your flight
per person
14 Oct - 21 Oct
found 7 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
9.4/10 Exceptional! (1,692 reviews)
Always a great stay. The folks here are always friendly, welcoming and helpful. A stone’s throw from the hotel is the Coffee Collective (formerly Firehook Bakery) for great coffee and pastries. The metro is right at the hotel for traveling around. If you don’t mind a walk it’s about a 40 minute walk to the Smithsonian.

Reviewed on 8 Aug 2025

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

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

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

Shady Side, MD
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, MD
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, MD
The price is £361 per night from 9 Aug to 10 Aug
£361
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 1,188 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Shady Side travel package cost?
The most affordable Shady Side travel package is £941, 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.