Shady Side Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Shady Side

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 S$205 per night from 24 Nov to 25 Nov
S$205
includes taxes & fees
24 Nov - 25 Nov
8.8/10 Excellent! (1,698 reviews)
"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."

Reviewed on 21 Nov,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 S$137 per night from 27 Nov to 28 Nov
S$137
includes taxes & fees
27 Nov - 28 Nov
6.2/10 (1,449 reviews)
"I first want to compliment the staff. The customer service representative was very cordial and professional I was impressed on the upkeep and cleanliness of the hotel property. I felt safe. My room was enormous and complimented my personality. When I book my next stay, I will definitely like to reserve ..."

Reviewed on 21 Nov,2024

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is S$209 per night from 24 Dec to 25 Dec
S$209
includes taxes & fees
24 Dec - 25 Dec
9.2/10 Wonderful! (1,001 reviews)
"The staff was the best always checking to see if I needed anything."

Reviewed on 19 Nov,2024

Graduate by Hilton Annapolis
See all 1,095 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?
Our Shady Side holiday packages, which begin from just , 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 holiday 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 holiday your way. We offer more than 550 airlines and 1,000,000 hotel options globally, so that everyone has a chance to travel and fulfil those holiday dreams.
Where should I stay in Shady Side?
Stay where the action is. Many travellers 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 holiday?
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 holiday package?
With a holiday 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 holiday 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 holiday 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.