Title: Top 10 Hotels in Shady Side, MD from $87 - Competitive Prices | Expedia.com [Shady Side Travel Guide](https://expedia.com/Shady-Side.dx6264943)[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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Shady Side Ocean view [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=OCEAN_VIEW) Great for families [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&travelerType=family_friendly) Pool [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=POOL) Pet-friendly [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=PETS) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=HOT_TUB) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=COTTAGE) Condo [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&lodging=CONDO) Waterpark [](https://www.expedia.com/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-25&d2=2026-02-25&amenities=WATER_PARK) ## Check prices for these dates Tonight [Feb 9 - Feb 10](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-02-09&endDate=2026-02-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 10 - Feb 11](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-02-10&endDate=2026-02-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side hotels ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/d3121313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/230b1a1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Waterfront - North Tower | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/431383cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort [](https://www.expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) Chesapeake Beach 8.4/10 Very Good (1,002 reviews) "Yes the room was clean and the staff was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thurnell $117 nightly $128 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/4973a39f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (869 reviews) "Nice staff and rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter $84 nightly $93 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/30dd84ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/4da4e372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (712 reviews) "Amazing location and staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi J. $118 nightly $131 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/cbbf2396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (132 reviews) "Beautiful hotel, nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim $143 nightly $154 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/e8c42422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/8ea761a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/d81dd69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Gambrills [](https://www.expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) Gambrills 9.0/10 Wonderful (1,012 reviews) "Great staff & clean rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmelo $85 nightly $97 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/c88d625f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/bc4b31c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/d7bfce72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Accessible, Non Smoking | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/831d18f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Conference Center [](https://www.expedia.com/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) Bowie 9.2/10 Wonderful (1,003 reviews) "Quiet lodging, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel $98 nightly $111 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/814e7667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/da259258.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/14b7e845.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8d29fbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Anchored Inn at Hidden Harbour Marina [](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) Deale 9.4/10 Exceptional (476 reviews) "Beautiful place to stay, we stay their one to two times a year." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marjorie $134 nightly $153 total Feb 11 - Feb 12 Total with taxes and fees [](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/0c127689.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/745b6ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/4d956ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Annapolis [](https://www.expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) Annapolis 9.0/10 Wonderful (1,004 reviews) "Great location and friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shana $93 nightly $106 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/fb2063de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/404be25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Down comforters, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/3c8a6fac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/a3be2d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG [](https://www.expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) Upper Marlboro 8.4/10 Very Good (1,006 reviews) "Nice and clean. Pleasant staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MICHELLE $89 nightly $101 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/b47730be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/c739becc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/ffd4eed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Largo/Washington DC [](https://www.expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) Upper Marlboro 8.2/10 Very Good (1,010 reviews) "Had a great stay. Room was nice and clean. Would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadine $98 nightly $110 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/4dfe2462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/c12dde92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/a8e6d435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Annapolis [](https://www.expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) Edgewater 8.8/10 Excellent (985 reviews) "We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olga $91 nightly $104 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business center](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very Good (1,001 reviews) "Nice breakfast, cleanroom. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne $83 nightly $93 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/2ee9107a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/58ff455e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Annapolis Downtown [](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) Annapolis 8.6/10 Excellent (1,005 reviews) "An amazing cozy place to stay during this snow storm!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) zhanna $96 nightly $109 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/676e246c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3996h2664x4y0-50b1ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/1182dd74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/97b0db53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites By Marriott Annapolis [](https://www.expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) Annapolis 9.0/10 Wonderful (173 reviews) "Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $110 nightly $125 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/ee980eab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/bc6750c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/e9e3336f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 2 Double Beds | Individually furnished, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/5eb26742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn [](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) St. Michaels 8.2/10 Very Good (1,000 reviews) "Good value and close to downtown." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John $103 nightly $114 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/e01c273a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Second Floor Bay View Double Room with Balcony | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/4f8f8af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/86e1ff48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/9f614534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Knapps Narrows Marina & Inn [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) Sherwood 9.4/10 Exceptional (368 reviews) "Always a great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randolph $100 nightly $110 total Feb 10 - Feb 11 Total with taxes and fees [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/9e6dd0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/19214323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking, Fireplace | Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/42a0faa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Annapolis, MD [](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) Annapolis 9.0/10 Wonderful (1,003 reviews) "Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda $94 nightly $107 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/2360f1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 5 AM to 11 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/f6f30f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1,000 reviews) "Staff was friendly and rooms were clean. Beautiful area to visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy $122 nightly $136 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Room, 1 King Bed, Non Smoking (Whirlpool) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/21b35d2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/59ba3f76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/9a55b500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/20400/20333/72559fa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Annapolis by IHG [](https://www.expedia.com/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) Annapolis 8.2/10 Very Good (1,001 reviews) " The rooms where clean, staff where so helpful. The cafe with a hot bar breakfast was excellent it was always clean and replenished with Great Coffee. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sherri $101 nightly $115 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Holiday-Inn-Express-Suites-Annapolis.h20333.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/c21b600a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,004 reviews) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Miguel $83 nightly $94 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-02-23&endDate=2026-02-24®ionId=6264943&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Hotels.d6264943.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Hotels.d6264943.Travel-Guide-Hotels) ## 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](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263308) ### 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. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263322) ## Top Shady Side Hotel Reviews ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Clean room. Friendly staff. Good food. " [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Nice staff" [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "The room was ready early and very clean..staff was very friendly " [](https://expedia.com/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Comfort Inn Largo-Washington DC East](https://images.trvl-media.com/lodging/1000000/20000/19400/19389/428ef9f4_y.jpg) ### Comfort Inn Largo-Washington DC East 10/10 Excellent "Yes" [](https://expedia.com/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Room was spotless. Staff was very courteous. Would highly recommended." [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "The room was very spacious. Staff were nice. Amenities were excellent. Good location for our stay." [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway](https://images.trvl-media.com/lodging/1000000/10000/6400/6366/b2f3a1ba_y.jpg) ### La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 10/10 Excellent "Very clean, nice service " [](https://expedia.com/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "We were happy to stay at this place. Very beautiful, warm, comfortable ❤️❤️❤️" [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 10/10 Excellent "Staff was super friendly and helpful - rooms had good sound proofing. I could hear a party going on while I was in the hallway but didn’t hear it at all in my room. My daughter had a competition the next day so the peace and quiet was important. " [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ## More cheap stays in Shady Side ![WoodSpring Suites Washington DC East Arena Drive](https://images.trvl-media.com/lodging/27000000/26600000/26597500/26597444/b9eed889_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### WoodSpring Suites Washington DC East Arena Drive 1603 Brightseat Rd. Hyattsville MD $77 nightly $87 total Feb 10 - Feb 11 Total with taxes and fees 6/10 (1,001 reviews) [](https://expedia.com/College-Park-Hotels-WoodSpring-Suites-Washington-DC-East-Arena-Drive.h26597444.Hotel-Information) ![Best Western Annapolis](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Annapolis 2520 Riva Rd Annapolis MD $79 nightly $90 total Feb 22 - Feb 23 Total with taxes and fees 7.6/10 Good! (1,000 reviews) [](https://expedia.com/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Microtel Inn & Suites by Wyndham Gambrills](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/b7d11ace_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Microtel Inn & Suites by Wyndham Gambrills 2525 Evergreen Rd. Gambrills MD $85 nightly $97 total Mar 1 - Mar 2 Total with taxes and fees 9/10 Wonderful! (1,009 reviews) [](https://expedia.com/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Hampton Inn & Suites Glenarden/Washington DC](https://images.trvl-media.com/lodging/20000000/19350000/19345400/19345309/114260b9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Glenarden/Washington DC 2901 Campus Way North Lanham MD $98 nightly $110 total Feb 16 - Feb 17 Total with taxes and fees 9/10 Wonderful! (1,008 reviews) [](https://expedia.com/College-Park-Hotels-Hampton-Inn-Suites-Glenarden.h19345309.Hotel-Information) ![Comfort Inn Conference Center](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn Conference Center 4500 Crain Hwy Bowie MD $98 nightly $111 total Feb 10 - Feb 11 Total with taxes and fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.com/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![St Michaels Inn](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### St Michaels Inn 1228 S Talbot Street St. Michaels MD $103 nightly $114 total Feb 17 - Feb 18 Total with taxes and fees 8/10 Very Good! (1,000 reviews) [](https://expedia.com/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Hotels in Shady Side with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 2 properties [](https://expedia.com/5Star-Shady-Side-Hotels.s50-0-d6264943.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 9 properties [](https://expedia.com/4Star-Shady-Side-Hotels.s40-0-d6264943.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 81 properties [](https://expedia.com/3Star-Shady-Side-Hotels.s30-0-d6264943.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 106 properties [](https://expedia.com/2Star-Shady-Side-Hotels.s20-0-d6264943.Travel-Guide-Filter-Hotels) ## Find out more about Shady Side ### Top reasons to visit Shady Side - **Outdoor Activities:** Shady Side offers a variety of outdoor adventures, perfect for families and nature enthusiasts, including marinas and parks. - **Charming Community Atmosphere:** Experience the friendly vibe of this scenic coastal town, ideal for relaxation and exploration. - **Proximity to Annapolis:** Just a short drive away, visitors can enjoy the vibrant culture and attractions of downtown Annapolis. - **Cozy Accommodations:** Choose from a range of charming hotels and bed & breakfasts, accommodating diverse traveler needs. - **Rich History:** Explore historic houses and cultural sites that showcase the area's unique heritage. ### Find great hotels near Shady Side Welcome to Shady Side, Maryland, where you can find a range of charming accommodations, including hotels and cozy bed & breakfasts. Whether you're seeking a pet-friendly stay or a welcoming environment for LGBTQIA travelers, Shady Side offers various options to suit your needs. Explore the best hotels in the area, perfect for both leisure and business travelers, and enjoy a memorable vacation experience in this picturesque coastal community. - **[Comfort Inn Conference Center: ](https://www.expedia.com/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information)** Ideal for business travelers, the Comfort Inn Conference Center combines practicality with comfort. Located 13 miles from Shady Side, this hotel is pet-friendly and offers a range of business amenities, including multiple meeting rooms and a fully equipped conference center. The property is designed with convenience in mind, featuring accessible business centers and a prime location in a bustling business district. Its welcoming atmosphere is perfect for both work and leisure, making it a solid choice for professionals on the go. - **Country Inn & Suites by Radisson, Annapolis, MD:** Just 10 miles from Shady Side, Country Inn & Suites is a 3-star gem that emphasizes inclusivity and comfort. This hotel is not only pet-friendly, but also proudly supports LGBTQIA travelers, making it a welcoming space for everyone. With 24-hour business center access, multiple meeting rooms, and a spacious conference area, it caters to the needs of corporate guests while providing a cozy atmosphere. Guests appreciate the dog exercise area and thoughtful pet policies, ensuring a pleasant stay for furry companions as well. - **[Graduate by Hilton Annapolis: ](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information)** Located 9 miles from Shady Side, the Graduate by Hilton Annapolis offers a sophisticated blend of family-friendly and business-oriented features. This 4-star hotel is perfect for travelers with pets, providing amenities such as food and water bowls and variable pet fees. Business travelers will find essential services like meeting rooms and conference spaces, while families with children can enjoy complimentary cribs. The Graduate stands out for its stylish design and commitment to delivering a memorable stay for all guests. ### Where to stay near Shady Side Shady Side, Maryland, offers a delightful mix of outdoor adventures and family-friendly experiences. Just a short drive from vibrant downtown Annapolis, visitors can enjoy the peaceful atmosphere while exploring the scenic Chesapeake Bay. This charming location is perfect for a relaxing getaway, where you can immerse yourself in the friendly community and discover the beauty of the region. Whether you're seeking a quiet escape or a taste of city life, Shady Side has something for everyone. - **[Annapolis: ](https://www.expedia.com/Annapolis-Hotels.d6034082.Travel-Guide-Hotels)** Located 10 miles from Shady Side, Annapolis is a vibrant city known for its rich history and charming waterfront. As the state capital of Maryland, it offers a mix of educational experiences, shopping opportunities, and outdoor activities. Visitors flock to Annapolis for family-friendly attractions and city-themed explorations, especially during the peak months from May to July. Highlights include historic sites like the U.S. Naval Academy, beautiful beaches, and scenic lakes. Enjoy shopping at local centers and indulging in the area’s diverse culinary scene while taking in the picturesque views of the Chesapeake Bay. - **[Deale: ](https://www.expedia.com/Deale-Hotels.d55664.Travel-Guide-Hotels)** Just 5 miles away from Shady Side, Deale is a small yet inviting city perfect for outdoor enthusiasts and adventure seekers. Known for its stunning scenery, visitors are drawn to Deale primarily in June to July and October. The town boasts recreational areas, shopping centers, and a laid-back atmosphere. Nature lovers can explore nearby beaches, lakes, and the national state park, which offers ample opportunities for hiking, fishing, and relaxing in nature. Whether you’re looking for a peaceful getaway or thrilling outdoor activities, Deale has something for everyone. - **[Galesville: ](https://www.expedia.com/Galesville-Hotels.d6264947.Travel-Guide-Hotels)** A mere 2 miles from Shady Side, Galesville is a quaint city that perfectly balances outdoor family fun and scenic beauty. With a peak in visitor numbers from June to August, this charming area offers recreational activities, educational experiences, and local shopping options. Galesville is well-known for its beautiful beaches, serene lakes, and inviting urban parks, making it an ideal spot for picnics, leisurely walks, or simply soaking up the sun. This close-knit community is sure to provide a relaxing and enjoyable atmosphere for all travelers. ### Things to do near Shady Side Shady Side, Maryland, is perfect for outdoor family vacations and urban adventures. Visitors can enjoy activities in recreational areas, explore educational sites, and indulge in shopping at local mall centers. With its charming community atmosphere, Shady Side offers a delightful blend of relaxation and engagement for tourists looking to experience the best of this scenic coastal town. **Shopping** In Shady Side, visit the [Wild Bird Center](https://www.expedia.com/Wild-Bird-Center-Hotels.0-l553248621532662329-0.Travel-Guide-Filter-Hotels), an 8-mile drive offering unique gifts for nature enthusiasts. If you're up for a drive, check out Annapolis Mall and [Westfield Annapolis Mall](https://www.expedia.com/Westfield-Annapolis-Mall-Hotels.0-l6172637-0.Travel-Guide-Filter-Hotels), both located 10 miles away, featuring a mix of entertainment, shopping, and dining options. **Recreation** [Navy-Marine Corps Memorial Stadium](https://www.expedia.com/Navy-Marine-Corps-Memorial-Stadium-Hotels.0-l6091645-0.Travel-Guide-Filter-Hotels) offers an energetic atmosphere perfect for sports enthusiasts. [South River Golf Links](https://www.expedia.com/South-River-Golf-Links-Hotels.0-l553248621532662267-0.Travel-Guide-Filter-Hotels) invites you to enjoy a round of golf amidst picturesque outdoor settings. For a touch of luxury, visit [Old South Country Club](https://www.expedia.com/Old-South-Country-Club-Hotels.0-l553248621532662175-0.Travel-Guide-Filter-Hotels), where you can unwind in a refined environment and enjoy premium amenities. **Adventure** At [Chesapeake Beach Water Park](https://www.expedia.com/Chesapeake-Beach-Water-Park-Hotels.0-l553248621532662257-0.Travel-Guide-Filter-Hotels), located 10 miles from Shady Side, enjoy thrilling water slides and family-friendly attractions for a day of fun. Experience the excitement of sailing at [Annapolis Sailing School](https://www.expedia.com/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), 9 miles away, offering outdoor adventure on the beautiful waters. Hike the scenic [B&A Trail](https://www.expedia.com/BA-Trail-Hotels.0-l553248621532662355-0.Travel-Guide-Filter-Hotels), situated 18 miles from Shady Side, for breathtaking views and natural beauty. **Nightlife** Experience a vibrant nightlife in Shady Side with a visit to [The Colonial Players](https://www.expedia.com/The-Colonial-Players-Hotels.0-l553248621532662280-0.Travel-Guide-Filter-Hotels) for a theatrical evening filled with culture and romance. For a more adventurous vibe, check out [Annapolis Bowl](https://www.expedia.com/Annapolis-Bowl-Hotels.0-l553248621532662328-0.Travel-Guide-Filter-Hotels) or [Crofton Bowl](https://www.expedia.com/Crofton-Bowl-Hotels.0-l553248621532662196-0.Travel-Guide-Filter-Hotels), both offering exciting arcade games and fun-filled activities just a short drive away. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Shady Side To save money on your trip to Shady Side, Maryland, consider visiting during the off-peak months of December to February for lower rates. Booking your stay on a Monday can also help reduce costs, while Saturdays tend to be pricier. Use Expedia to find budget-friendly accommodations by sorting options from lowest to highest price, and explore package deals that combine flights and hotels for additional savings. Joining the Expedia One Key membership can unlock exclusive discounts and allow you to earn OneKeyCash for future stays. Don't forget to look for free local activities to enhance your experience without extra costs. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Shady Side are December to February, where the prices are slightly lower. This is in comparison to May to July, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Shady Side is Monday. The most expensive day to stay in Shady Side is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your options based on your budget, preferred location, and the type of hotel you desire. To find the best prices and deals, simply arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Shady Side with your flights and activities by opting for an Expedia package deal. - **Become a One Key member:** Join [Expedia's One Key membership](https://www.expedia.com/welcome-one-key) program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels. ### Find the best attractions in and around Shady Side Shady Side, Maryland, offers a perfect blend of outdoor activities, family fun, and urban exploration. Visitors can enjoy local attractions such as marinas, historic houses, and urban parks that cater to those seeking cultural experiences and nature. Whether you're looking to relax by the water or explore the rich history of the area, Shady Side has something for everyone to enjoy. - **[U.S. Naval Academy: ](https://www.expedia.com/US-Naval-Academy-Hotels.0-l6077390-0.Travel-Guide-Filter-Hotels)** Located 10 miles from Shady Side, this prestigious military academy offers a blend of history and stunning architecture. Visitors can explore the beautiful campus, learn about naval traditions, and enjoy scenic views along the waterfront. - **[Shadyside Park: ](https://www.expedia.com/Shadyside-Park-Hotels.0-l6263308-0.Travel-Guide-Filter-Hotels)** Situated within Shady Side, this urban park is a perfect spot for families to unwind. With playgrounds, picnic areas, and walking trails, it provides a relaxing outdoor atmosphere in a vibrant city setting. - **[Captain Avery Museum: ](https://www.expedia.com/Captain-Avery-Museum-Hotels.0-l6263322-0.Travel-Guide-Filter-Hotels)** Also located in Shady Side, this historic house museum showcases local maritime history and culture. Visitors can engage with exhibits and artifacts that highlight the area's rich heritage and connection to the Chesapeake Bay. ### Best time to go to Shady Side The best time to visit Shady Side can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Shady Side falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Shady Side falls in January, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 35.8°F (2.1°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 38.1°F (3.4°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 45.0°F (7.2°C) | Light Rain | Mostly Sunny | Average | Average | | April | 55.0°F (12.8°C) | Light Rain | Mostly Sunny | Average | Average | | May | 64.2°F (17.9°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | June | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 78.3°F (25.7°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 76.6°F (24.8°C) | Light Rain | Mostly Sunny | Average | Average | | September | 70.7°F (21.5°C) | Light Rain | Mostly Sunny | Average | Average | | October | 60.4°F (15.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | November | 48.7°F (9.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 41.5°F (5.3°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Shady Side Visiting Shady Side, Maryland, is convenient with three major airports nearby. Washington, DC ([DCA](https://www.expedia.com/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)\-Ronald Reagan Washington National) is situated 28 miles away, with hotels like the InterContinental Washington D.C. - The Wharf and [Riggs Washington DC](https://www.expedia.com/Washington-Hotels-Riggs-Washington-DC.h37192042.Hotel-Information) just 2 to 3 miles from the airport. Another option is Washington, DC ([IAD](https://www.expedia.com/Washington-Dulles-Intl-Airport-Hotels.0-aIAD-0.Travel-Guide-Filter-Hotels)\-Washington Dulles Intl.), located 51 miles away, featuring the [Hyatt Regency Dulles](https://www.expedia.com/Herndon-Hotels-Hyatt-Regency-Dulles.h150.Hotel-Information) and [Hilton Washington Dulles Airport](https://www.expedia.com/Herndon-Hotels-Hilton-Washington-Dulles-Airport.h27218.Hotel-Information) within a couple of miles. Baltimore, MD ([BWI](https://www.expedia.com/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)\-Baltimore Washington Intl. Thurgood Marshall), only 25 miles from Shady Side, offers luxury accommodations like [Sagamore Pendry Baltimore](https://www.expedia.com/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [Four Seasons Hotel Baltimore](https://www.expedia.com/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information), both about 8 miles away, providing shuttle services to the airport. ## Frequently asked questions ### What is the best area to stay in Shady Side? > This area offers direct access to the Chesapeake Bay and West River, providing a scenic backdrop for your stay. You'll find many properties with water views, private docks, and outdoor spaces superb for enjoying the coastal environment. The general layout is residential, with properties spread out along the shoreline and smaller roads leading to the water. > > > Couples looking for a relaxing getaway will appreciate the tranquility and natural beauty of the waterfront. Many accommodations here offer private settings, ideal for unwinding, enjoying sunsets over the water, and perhaps even engaging in water-based activities like kayaking or paddleboarding directly from their rental. > > > Families will also find the waterfront appealing due to the spacious properties and opportunities for outdoor recreation. Children can enjoy exploring the shoreline, and many homes come equipped with amenities like private pools or yards, offering plenty of space for activities. ### When is the best time to go to Shady Side? > During these months, the temperatures are mild, typically ranging from the 60s to high 70s Fahrenheit, making it ideal for outdoor activities without the humidity of summer or the chill of winter. This period is great for couples or solo travelers looking for a comfortable and tranquil getaway, as they can enjoy waterfront dining and exploring the local parks without large crowds. > > > Summer, from mid-June to August, is also a popular time, especially for families. While it can be warmer and more humid, with temperatures often in the 80s, this is when all water-based activities are in full swing. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Shady Side hotel booking with Expedia? > \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo. ### How much is the nightly rate at a Shady Side hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Washington Hotels ](https://www.expedia.com/Washington-Hotels.d178318.Travel-Guide-Hotels) - [Hotels near Shadyside Park ](https://www.expedia.com/Shadyside-Park-Hotels.0-l6263308-0.Travel-Guide-Filter-Hotels) - [Hotels near Captain Avery Museum ](https://www.expedia.com/Captain-Avery-Museum-Hotels.0-l6263322-0.Travel-Guide-Filter-Hotels) - [Galesville Hotels ](https://www.expedia.com/Galesville-Hotels.d6264947.Travel-Guide-Hotels) - [B&B in Galesville ](https://www.expedia.com/Galesville-Bed-And-Breakfast.d6264947-aaBedAndBreakfast.Travel-Guide-Accommodation) - [3 Star Hotels in Galesville ](https://www.expedia.com/3Star-Galesville-Hotels.s30-0-d6264947.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Galesville ](https://www.expedia.com/4Star-Galesville-Hotels.s40-0-d6264947.Travel-Guide-Filter-Hotels) - 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