Shady Side Vacation Packages

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Your Shady Side Vacation

Take the stress out of travel planning by booking a Shady Side vacation package. One of the best neighborhoods 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 vacation is clicks away. Explore flights, hotels and more on Expedia for an adventure that's tailored to suit your style.

Top Shady Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
per person
Aug. 5 - Aug. 8
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Washington (DCA)
8.2/10 Very Good! (1,022 reviews)
Everything about this hotel is perfection! The rooms are huge and beautifully decorated. The location is quiet yet also close to many amazing restaurants. Definitely go see Moises at Circo, the hotel bar....his berry Sangria is to die for! Its about 1.8 miles from city center which can be walked if you're up for it or you can easily catch an Uber with little to no wait time. There is a metro station right around the corner and those electric scooter/bikes right outside. The hotel also offers bike rentals! The staff were very welcoming and friendly. Honestly I can't say enough to praise this place. If you're visiting DC this is the place to be!

Reviewed on Jun. 17, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
per person
Aug. 26 - Aug. 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,340 reviews)
We love it here. It’s our 3rd trip !!!

Reviewed on Jun. 16, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Aug. 5 - Aug. 8
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
Wonderful staff and great customer service. Accomodations were comfortable and the food was excellent.

Reviewed on Jun. 17, 2024

Kimpton George Hotel, an IHG Hotel

Kimpton George Hotel, an IHG Hotel

4.5 out of 5
Northwest
per person
Aug. 5 - Aug. 8
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
The restaurant was closed on Saturday for breakfast and dinner. The bathroom door was a “barn” style that had a 1” gap between the door/wall which did not allow privacy. There was no valet service.

Reviewed on Jun. 15, 2024

The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel

The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel

4 out of 5
Northwest
per person
Aug. 5 - Aug. 8
found 14 hours ago
Roundtrip flight included
Detroit (DTW) to Washington (DCA)
8.8/10 Excellent! (325 reviews)
Very welcoming staff and right next to the metro station for easy transit around the city. There was also a fun playroom, nice fitness center and a cool rooftop with a bar and pool. $71 for valet per night was upsetting to hear but we did it.

Reviewed on Jun. 16, 2024

Shady Side Hotel Deals

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 CA $188 per night from Jul. 3 to Jul. 4
CA $188
CA $245 total
includes taxes & fees
Jul 3 - Jul 4
8.8/10 Excellent! (1,626 reviews)
"Lovely historic property in a perfect location. The front desk staff are professional and knowledgeable, the rooms comfortable and clean, the shopping and dining options endless. Highly recommend."

Reviewed on Jun. 15, 2024

Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jun. 20 to Jun. 21
CA $147
CA $167 total
includes taxes & fees
Jun 20 - Jun 21
6.4/10 (1,292 reviews)
"Great hotel"

Reviewed on Jun. 17, 2024

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $244 per night from Jul. 1 to Jul. 2
CA $244
CA $278 total
includes taxes & fees
Jul 1 - Jul 2
9.2/10 Wonderful! (1,033 reviews)
"We had a nice time for our baby moon!"

Reviewed on Jun. 14, 2024

Graduate Annapolis
See all 1,089 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Shady Side vacation package cost?
Our Shady Side vacation packages, which begin from just CA $565, are an easy way to save loads of cash. Select your preferred flights, hotels and rental cars to create your dream itinerary.
How do I get a cheap travel package to Shady Side?
Simply by bundling. Flights, hotels and rental cars — combine whatever you need into a Shady Side vacation package and save. Score even more deals when you include extras such as tours or experiences to your booking. But that’s not the only impressive part. You have the freedom to tailor your vacation your way. We offer more than 550 airlines and 1,000,000 hotel options globally, so that everyone has a chance to travel and fulfill those vacation dreams.
Where should I stay in Shady Side?
Stay where the action is. Many travelers like to book hotels within easy reach of top attractions, like Shadyside Park, Franklin Point State Park and Captain Avery Museum.
What are the top hotels in Shady Side?
If it’s comfort and convenience you’re seeking, it’s hard to beat Luxe Chesapeake Bay Getaway < 20 Mi To Annapolis. Spend your evenings relaxing here and your days roaming around Shady Side’s best sights.
How far in advance should I book my Shady Side vacation?
It’s hard to pick the ideal time for airfares, but we generally say the earlier, the better. Many international flights on Expedia become available up to 12 months in advance. If you’re unable to do so, don’t worry. Discounted prices occasionally appear just weeks before departure dates.
What does an Expedia Shady Side travel package include?
Hotels, rental cars and flights, or any combination of the three — the choice is yours. Whether you’re exploring Shady Side with the whole family or enjoying a solo break, there’s a package to match every style and budget. Once you’ve made your booking, why not add on some tours as well?
What should I know before booking a Shady Side travel package?
When you book your flights, hotels and car rentals together, you’ll enjoy incredible discounts. Whether you’re planning a beach break in a villa or prefer to stay in an upscale city hotel, Expedia will help make it happen.
Can I choose my airline with a Shady Side Expedia vacation package?
With a vacation package, you’re always in charge. Whether you’d prefer to fly to Shady Side in economy or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Shady Side vacation package?
Because we know life can be unpredictable, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you’ve booked your Shady Side vacation package in the last 24 hours, you may be able to cancel or change it free of charge. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Shady Side

Image for Shadyside Park

Shadyside Park

Explore the great outdoors at Shadyside Park, a lovely green space in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Shadyside Park
Image for Captain Avery Museum

Captain Avery Museum

You can spend time exploring the galleries in Captain Avery Museum in Shady Side. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Captain Avery Museum

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.