Title: Visit Shady Side: 2026 Travel Guide for Shady Side, Maryland | Expedia.com [Hotels in Shady Side](https://expedia.com/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.com/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.com/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Car Rentals in Shady Side](https://expedia.com/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.com/Shady-Side.d6264943.Destination-Travel-Guides) # Shady Side, MD ## Travel Guide ## Visit Shady Side Things to do ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=DX_SPRING_PROMO_6264943) - Shady Side Hotel Deals - Vacation Rentals in Shady Side ![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 $171 nightly $195 total Mar 29 - Mar 30 Total with taxes and 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! (1,000 reviews) Central l9cation, easy walk to all sites. Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=6264943) ![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 $106 nightly $120 total Mar 30 - Mar 31 Total with taxes and 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! (1,003 reviews) ⭐️⭐️⭐️⭐️ Reviewed on Mar 7, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=21463&PinnedHotelID=21463&HadPinnedHotel=true®ionId=6264943) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Annapolis by IHG 173 Jennifer Rd Annapolis MD $110 nightly $125 total Mar 17 - Mar 18 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 helpful staff and the ... 8.8/10 Excellent! (1,001 reviews) Room was clean Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F17%2F2026&endDate=3%2F18%2F2026&selected=7668&PinnedHotelID=7668&HadPinnedHotel=true®ionId=6264943) [See all 1,184 properties in Shady Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F14%2F2026&endDate=3%2F15%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. ![Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/0100abcb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side Shady Side MD Stay at this vacation home in Shady Side. Enjoy laundry facilities and air conditioning. Popular attractions Shadyside Park and Franklin Point State Park are ... 10/10 Exceptional! (4 reviews) Very comfortable bedrooms and sitting area. Perfect location for the event we were attending. Very clean. Friendly host. Reviewed on Oct 14, 2025 [](https://expedia.com/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.Hotel-Information) ![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! (49 reviews) This was a terrific experience. The house boat was extremely clean and well taken care of. The host was proactive with terrific communication. She was upfront with the care and expectations of the stay. It was well stocked, perfect for cooking and enjoying the views from the boat. We are already ... Reviewed on Mar 11, 2026 [](https://expedia.com/Stevensville-Hotels-Chesapeake-Houseboat-Getaway-On-Kent-Island.h99712854.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! (198 reviews) We had a wonderful time and really enjoyed the back screened in porch which is where we spent a lot of time with our two little dogs. Reviewed on Mar 12, 2026 [](https://expedia.com/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.com/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.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-03-13&endDate=2026-03-14)[Mar 13 - Mar 14](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-03-13&endDate=2026-03-14) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-03-14&endDate=2026-03-15)[Mar 14 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2026-03-14&endDate=2026-03-15) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=3%2F13%2F2026&endDate=3%2F15%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.com/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. 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[Shadyside Park ](https://www.expedia.com/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction) - [Captain Avery Museum ](https://www.expedia.com/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction) - [Visit Galesville ](https://www.expedia.com/Galesville.dx6264947) - [Visit Churchton ](https://www.expedia.com/Churchton.dx6247936) - [Smithsonian Environmental Research Center ](https://www.expedia.com/Smithsonian-Environmental-Research-Center-Edgewater.d553248621532662265.Vacation-Attraction) - [Visit Deale ](https://www.expedia.com/Deale.dx55664) - [Visit Lothian ](https://www.expedia.com/Lothian.dx3000440697) - [Visit Tracys Landing ](https://www.expedia.com/Tracys-Landing.dx3000440927) - [Visit Oyster Harbor ](https://www.expedia.com/Annapolis-Oyster-Harbor.dx553248635976482330) - [Thanksgiving Farm Wines ](https://www.expedia.com/Thanksgiving-Farm-Wines-Maryland.d553248621532662264.Vacation-Attraction) - [Visit Edgewater ](https://www.expedia.com/Edgewater.dx6348965) - [Maryland Quiet Waters Park ](https://www.expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Car rentals near Captain Avery Museum ](https://www.expedia.com/Car-Rentals-In-Captain-Avery-Museum.d6263322.Car-Rental-Guide) - [Car rentals near Galesville ](https://www.expedia.com/Car-Rentals-In-Galesville.d6264947.Car-Rental-Guide) - [Car rentals near Churchton ](https://www.expedia.com/Car-Rentals-In-Churchton.d6247936.Car-Rental-Guide) - [Car rentals near Beverly Beach ](https://www.expedia.com/Car-Rentals-In-Beverly-Beach.d553248635975869024.Car-Rental-Guide) - [Car rentals near Mayo ](https://www.expedia.com/Car-Rentals-In-Mayo.d553248634998988486.Car-Rental-Guide) - [Car rentals near Cape Anne ](https://www.expedia.com/Car-Rentals-In-Cape-Anne.d553248635976386052.Car-Rental-Guide) - [Car rentals near Deale Beach ](https://www.expedia.com/Car-Rentals-In-Deale-Beach.d553248635975876712.Car-Rental-Guide) - [Car rentals near West River ](https://www.expedia.com/Car-Rentals-In-West-River.d553248635975860906.Car-Rental-Guide) - [Car rentals near Deale ](https://www.expedia.com/Car-Rentals-In-Deale.d55664.Car-Rental-Guide) - [Car rentals near Selby-on-the-Bay ](https://www.expedia.com/Car-Rentals-In-Selby-On-The-Bay.d553248634999271692.Car-Rental-Guide) - [Car rentals near Lothian ](https://www.expedia.com/Car-Rentals-In-Lothian.d3000440697.Car-Rental-Guide) - [Car rentals near Harwood ](https://www.expedia.com/Car-Rentals-In-Harwood.d553248635975850804.Car-Rental-Guide) - [Car rentals near Tracys Landing ](https://www.expedia.com/Car-Rentals-In-Tracys-Landing.d3000440927.Car-Rental-Guide) - [Car rentals near Highland Beach ](https://www.expedia.com/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide) - [Car rentals near Hillsmere Shores ](https://www.expedia.com/Car-Rentals-In-Hillsmere-Shores.d553248634998892012.Car-Rental-Guide) - [Car rentals near Edgewater ](https://www.expedia.com/Car-Rentals-In-Edgewater.d6348965.Car-Rental-Guide) - [Churchton Vacation Rentals ](https://www.expedia.com/Churchton-Vacation-Rentals.d6247936.Travel-Guide-VacationRentals) - [Deale Vacation Rentals ](https://www.expedia.com/Deale-Vacation-Rentals.d55664.Travel-Guide-VacationRentals) - [Edgewater Vacation Rentals ](https://www.expedia.com/Edgewater-Vacation-Rentals.d6348965.Travel-Guide-VacationRentals) - [Things to do in Edgewater ](https://www.expedia.com/Things-To-Do-In-Edgewater.d6348965.Travel-Guide-Activities) - Cities near Shady Side - Places of interest [Churchton](https://expedia.com/Churchton.dx6247936)[Galesville](https://expedia.com/Galesville.dx6264947) - [Shadyside Park ](https://expedia.com/Shadyside-Park-Shady-Side.d6263308.Vacation-Attraction) - [Captain Avery Museum ](https://expedia.com/Captain-Avery-Museum-Shady-Side.d6263322.Vacation-Attraction) - [U.S. Naval Academy ](https://expedia.com/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Annapolis City Dock ](https://expedia.com/Annapolis-City-Dock-Historic-District.d553248633992240262.Vacation-Attraction) - [Chesapeake Bay Bridge ](https://expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Westfield Annapolis Mall ](https://expedia.com/Westfield-Annapolis-Mall-Annapolis.d6172637.Vacation-Attraction) - [Sandy Point State Park ](https://expedia.com/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) - [Show Place Arena ](https://expedia.com/Show-Place-Arena-Upper-Marlboro.d6091739.Vacation-Attraction) - [Maryland State House ](https://expedia.com/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) - [Navy-Marine Corps Memorial Stadium ](https://expedia.com/Navy-Marine-Corps-Memorial-Stadium-Annapolis.d6091645.Vacation-Attraction) - [Anne Arundel Medical Center ](https://expedia.com/Anne-Arundel-Medical-Center-Annapolis.d553248621580159030.Vacation-Attraction) - [Annapolis Mall Shopping Center ](https://expedia.com/Annapolis-Mall-Shopping-Center-Annapolis.d553248621563220690.Vacation-Attraction) - [Bowie State University ](https://expedia.com/Bowie-State-University-Bowie.d6075472.Vacation-Attraction) - [Chesapeake Bay Maritime Museum ](https://expedia.com/Chesapeake-Bay-Maritime-Museum-Downtown-St-Michaels.d553248633992441010.Vacation-Attraction) - 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