Shady Side, MD

Travel Guide

A river with boats, a marina, and a town with houses and buildings.
An aerial view of a beach with clear water, a sandy shore, and visible footprints.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (44 reviews)
"Family members used this property for a home base so we could take day trips to Annapolis, DC and other small towns. Nice home with comfortable beds, nice linens and a fully stocked kitchen in a quiet neighborhood. The wood floors & fenced back yard were great for our dog, also appreciated the off-street ..."

Reviewed on Oct 17, 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
$85 nightly
The price is $96 total per night from Nov 9 to Nov 10
$96 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
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
$125 nightly
The price is $143 total per night from Dec 1 to Dec 2
$143 total
Dec 1 - Dec 2
Total with taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
Historic Inns of Annapolis
See all 1,221 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.
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
Book a stay at this family-friendly vacation home in Shady Side. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Shadyside Park and Captain ...
9.6/10 Exceptional! (44 reviews)
"Family members used this property for a home base so we could take day trips to Annapolis, DC and other small towns. Nice home with comfortable beds, nice linens and a fully stocked kitchen in a quiet neighborhood. The wood floors & fenced back yard were great for our dog, also appreciated the off-street ..."

Reviewed on Oct 17, 2026

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River

Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River

Arnold MD
Stay at this cottage in Arnold. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Annapolis City Dock and Bay Hills Golf Club are located ...
10/10 Exceptional! (5 reviews)
"Great location, excellent quality accommodations. Host communication was quick and helpful."

Reviewed on Oct 27, 2026

Waterfront Estate Renting 4BR Guest Cottage w/waterviews of Magothy River
Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access

Crownsville MD
Stay at this vacation home in Crownsville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Joyces Marina and B&A Trail are located ...
9.8/10 Exceptional! (31 reviews)
"Very nice place, clean and updated! We enjoyed our time there"

Reviewed on Nov 1, 2026

Cute, Cozy 2-bedroom house near Annapolis with water access
See all 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.

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 savor its top-notch restaurants.
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Frequently asked questions

When is the best time to visit Shady Side?
The best time to visit Shady Side is from May through September, when the weather is generally warm and pleasant. For fewer crowds and better value, the quieter months of November through February are a good bet, offering a cooler climate for exploring.
What is Shady Side known for?
Shady Side is known for being home to the Captain Avery Museum, offering travelers a glimpse into local history and culture. It also features Shadyside Park, providing pleasant green spaces for relaxation and outdoor activities.
What is a good itinerary length for Shady Side?
A good itinerary length for Shady Side is one to two days to explore local highlights like the Captain Avery Museum and Shadyside Park. For a more relaxed visit, two to three days would allow travelers to fully enjoy these points of interest and the natural surroundings.
What are the top things to do in and around Shady Side?
In Shady Side, travelers can visit the Captain Avery Museum, a local landmark, and explore Shadyside Park, a natural area.
Can I book a refundable hotel in Shady Side?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Shady Side by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Shady Side with Expedia?
Expedia makes it easier to plan your Shady Side trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Shady Side?
The best choice depends on your travel style. Hotels in Shady Side can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Shady Side trip on Expedia?
Once you've booked your Shady Side trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Shady Side trip?
Expedia offers customer support before, during, and after your Shady Side trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Shady Side?
If it's your first trip to Shady Side, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Shady Side hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Shady Side hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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