Title: Visit Shady Side: Best of Shady Side Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Shady Side](https://expedia.ca/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.ca/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.ca/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Shady Side Car Rentals](https://expedia.ca/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.ca/Shady-Side.d6264943.Destination-Travel-Guides) # Shady Side ## Travel Guide ## Visit Shady Side Things to do - Shady Side Hotel Deals - Vacation Rentals in Shady Side ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Largo/Washington DC 9100 Basil Court Upper Marlboro MD CA $159 CA $179 total Apr 14 - Apr 15 includes taxes & fees Book a stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Northwest ... 8.2/10 Very Good! (1,000 reviews) The management team was horrible. My grandson and i played in the pool ( which was dirty ) with a nerf football alll afternoon with no problems. We attempted to go back around 6pm with the same nerf football and we were told that it wasnt allowed....there was no signs specifically addressing this ... Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=21463&PinnedHotelID=21463&HadPinnedHotel=true®ionId=6264943) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Graduate by Hilton Annapolis 126 West St Annapolis MD CA $270 CA $308 total Apr 5 - Apr 6 includes taxes & fees Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ... 9.4/10 Exceptional! (1,005 reviews) The room was clean and comfortable. The hotel was decorated with a fun nautical theme. The location is excellent and close to dining and shopping. Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=6264943) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD CA $180 CA $253 total Apr 19 - Apr 20 includes taxes & 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 ... 9/10 Wonderful! (1,870 reviews) We had a great stay. Location couldn’t be better. Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=6264943) [See all 1,181 properties in Shady Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=6264943) 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. ![Chesapeake Houseboat Getaway on Kent Island, Maryland](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/64b6a56c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Houseboat Getaway on Kent Island, Maryland Stevensville MD Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ... 9.8/10 Exceptional! (50 reviews) Julia was fantastic! We came with 6 ladies for a surprise bachelorette weekend. She even gave us recommendations for super fun local venues and restaurants accounting for what was closed in the ‘off-season’. I don’t think there can be an off-season here. Everyone was so friendly and helpful with ... Reviewed on Mar 23, 2026 [](https://expedia.ca/Stevensville-Hotels-Chesapeake-Houseboat-Getaway-On-Kent-Island.h99712854.Hotel-Information) ![Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. ](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/4d0e4029_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. Stevensville MD Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Northern ... 10/10 Exceptional! (16 reviews) This was our second time spending Thanksgiving week at Woodland Retreat. We appreciate the overall cleanliness of the house. All the beds are very comfortable. The kitchen is well stocked. The primary suite has plenty of room for baby’s portable crib. The downstairs bonus room is ideal for family ... Reviewed on Nov 30, 2025 [](https://expedia.ca/Stevensville-Hotels-Woodland-Retreat-On-Kent-Island-5-Beds.h101278078.Hotel-Information) ![Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/b1486943_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch Saint Michaels MD Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are ... 9.8/10 Exceptional! (200 reviews) A lovely home just a block from the shops and restaurants on Talbot Street. The rear addition adds generous living space while preserving the charm of the historic house. The screened-in back deck is a great feature for relaxing evenings.Upstairs, the bedroom feels like a second retreat—spacious, ... Reviewed on Mar 30, 2026 [](https://expedia.ca/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information) [See all properties in Shady Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6264943&sort=VACATION_RENTAL) 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. ## Check Shady Side hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-04-01&endDate=2026-04-02)[Apr 1 - Apr 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-04-01&endDate=2026-04-02) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-04-02&endDate=2026-04-03)[Apr 2 - Apr 3](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-04-02&endDate=2026-04-03) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026) ### Popular places to visit #### 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. [](https://expedia.ca/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction) #### 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. [](https://expedia.ca/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction) - Cities near Shady Side - Places of interest [Churchton](https://expedia.ca/Churchton.dx6247936) - [Shadyside Park ](https://expedia.ca/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction) - [U.S. Naval Academy ](https://expedia.ca/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.ca/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Chesapeake Bay Bridge ](https://expedia.ca/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Sandy Point State Park ](https://expedia.ca/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) - [Maryland State House ](https://expedia.ca/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) - [Maryland Quiet Waters Park ](https://expedia.ca/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.ca/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Chesapeake Beach Water Park ](https://expedia.ca/Chesapeake-Beach-Water-Park-Chesapeake-Beach.d553248621532662257.Vacation-Attraction) - [Hammond-Harwood House ](https://expedia.ca/Hammond-Harwood-House-Historic-District.d6077396.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app