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! (39 reviews)
"Great yard for dog to run!"

Reviewed on Aug 27, 2026

Get rates
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$83 nightly
The price is $95 total per night from Sep 27 to Sep 28
$95 total
Sep 27 - Sep 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$147 nightly
The price is $168 total per night from Sep 27 to Sep 28
$168 total
Sep 27 - Sep 28
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 1,222 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! (39 reviews)
"Great yard for dog to run!"

Reviewed on Aug 27, 2026

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
9.6/10 Exceptional! (19 reviews)
"We had a lovely stay at this charming cottage on the bay. Everything was well maintained, the host provided strong communication, the grounds are beautiful, and our family found the hot tub to be a wonderful place to both relax amidst nature and reconnect . Also our 2 little dogs felt very much at ..."

Reviewed on Aug 3, 2026

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"

Reviewed on Aug 24, 2026

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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.
See properties

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.

Explore a world of travel with Expedia