Title: Shady Side Travel Guide: Best of Shady Side, Maryland Travel 2026 | Expedia.co.uk [Hotels in Shady Side](https://expedia.co.uk/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Holiday Rentals in Shady Side](https://expedia.co.uk/Shady-Side-Holiday-Rentals.d6264943.Travel-Guide-HolidayRentals)[Shady Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Shady-Side.d6264943.Car-Hire-Guide)[Shady Side Holidays](https://expedia.co.uk/Shady-Side.d6264943.Holidays-City-Breaks) # Shady Side Travel Guide ## Tourist Guide ## Visit Shady Side Things to do - Top hotels in Shady Side - Top Holiday Rentals in Shady Side ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court Annapolis MD £64 4 Jan - 5 Jan 2026 includes taxes & fees Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ... 8.6/10 Excellent! (1,008 reviews) We stayed there for 7 days and loved it. The breakfast was so good (the bagel with bacon, cheddar cheese, and egg was delicious)! We loved the large TV in the room, the beds were very comfy, the room was spacious and we were so grateful that the staff wiped off the cars after it snowed. The fire ... Reviewed on 18 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=3040&PinnedHotelID=3040&HadPinnedHotel=true®ionId=6264943) ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Largo/Washington DC 9100 Basil Court Upper Marlboro MD £77 4 Jan - 5 Jan 2026 includes taxes & fees Stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge) and a 24-hour fitness centre. Popular attractions Northwest ... 8/10 Very Good! (1,003 reviews) Good location Reviewed on 17 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=21463&PinnedHotelID=21463&HadPinnedHotel=true®ionId=6264943) ![La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway](https://images.trvl-media.com/lodging/1000000/10000/6400/6366/b2f3a1ba_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 55 Hampton Park Blvd Capitol Heights MD £71 26 Dec - 27 Dec includes taxes & fees Stay at this business-friendly hotel in Capitol Heights. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the clean rooms in their reviews. ... 5.8/10 (1,968 reviews) It was good for one night... The smell of the room when entered wasn't pleasant. Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=26%2F12%2F2025&endDate=27%2F12%2F2025&selected=6366&PinnedHotelID=6366&HadPinnedHotel=true®ionId=6264943) [See all 1,160 properties in Shady Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=23%2F12%2F2025&endDate=24%2F12%2F2025®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. ![Bay views with kayaks, bikes, fire pit, crabbing and more](https://images.trvl-media.com/lodging/92000000/91930000/91922300/91922203/e16e647f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bay views with kayaks, bikes, fire pit, crabbing and more Shady Side MD Stay at this family-friendly holiday home in Shady Side. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Shadyside Park and Captain Avery ... 9.6/10 Exceptional! (22 reviews) This is a quiet neighborhood with friendly neighbors. Very did friendly as well! Reviewed on 30 Nov 2025 [](https://expedia.co.uk/Shady-Side-Hotels-Bay-Views-With-Kayaks-Fire-Pit-Crabbing.h91922203.Hotel-Information) ![Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side](https://images.trvl-media.com/lodging/117000000/116010000/116005700/116005601/5eca3b46_edited_e784_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 holiday 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 14 Oct 2025 [](https://expedia.co.uk/Shady-Side-Hotels-Peaceful-2-Bedroom-2-Bathroom-House-With-WiFi-And-AC-In-Serene-Shady-Side.h116005601.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 Stay at this golf holiday home in Stevensville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Matapeake State Park and Northern Chesapeake ... 9.8/10 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 30 Nov 2025 [](https://expedia.co.uk/Stevensville-Hotels-Woodland-Retreat-On-Kent-Island-5-Beds.h101278078.Hotel-Information) [See all properties in Shady Side](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2025-12-22&endDate=2025-12-23)[22 Dec - 23 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2025-12-22&endDate=2025-12-23) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2025-12-23&endDate=2025-12-24)[23 Dec - 24 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=2025-12-23&endDate=2025-12-24) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[26 Dec - 28 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=02%2F01%2F2026&endDate=04%2F01%2F2026)[2 Jan - 4 Jan](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6264943&startDate=02%2F01%2F2026&endDate=04%2F01%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 savour its top-notch restaurants. [](https://expedia.co.uk/Shadyside-Park-Shady-Side.d6263308.Attraction) #### Captain Avery Museum You can spend time exploring the galleries in Captain Avery Museum during your trip to Shady Side. Stroll along the area's waterfront or simply savour its top-notch restaurants. 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