Title: Hotels in Shady Side, MD - Best Shady Side Hotels from £64 - Fully Refundable Options - Expedia.co.uk [Shady Side Travel Guide](https://expedia.co.uk/Shady-Side.dx6264943)[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) ![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) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/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 Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&amenities=POOL) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&lodging=APARTMENT) Sea view [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&amenities=OCEAN_VIEW) House­boat [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&lodging=HOUSE_BOAT) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&travelerType=family_friendly) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&amenities=HOT_TUB) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&lodging=COTTAGE) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&amenities=PETS) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Shady+Side%2C+Maryland%2C+United+States+of+America®ionId=6264943&latLong=38.841782%2C-76.512176&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-05&d2=2026-03-05&lodging=CONDO) ## Check prices for these dates Tonight [17 Feb - 18 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-02-17&endDate=2026-02-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Feb - 19 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-02-18&endDate=2026-02-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-02-20&endDate=2026-02-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6264943&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side hotels ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.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) ### Best Western Kent Narrows Inn [](https://www.expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very good (1,001 reviews) - Waterside hotel with scenic sunset views and a refreshing indoor pool. "Nice breakfast, cleanroom. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne £76 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![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) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.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) ![Hair salon](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/45498263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort [](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) Chesapeake Beach 8.4/10 Very good (1,005 reviews) "Yes the room was clean and the staff was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thurnell £95 includes taxes & fees 23 Feb - 24 Feb [](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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 room](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/8dfe0c39.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.co.uk/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 £112 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.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) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/d898936b.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) ### Knapps Narrows Marina & Inn [](https://www.expedia.co.uk/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) Sherwood 9.4/10 Exceptional (369 reviews) - Experience waterfront tranquility at this bay-side retreat with kayaking and bikes. "Always a great time. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randolph £81 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.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) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/e9e3336f.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) ![View from property](https://images.trvl-media.com/lodging/1000000/20000/10300/10281/76eda657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Michaels Inn [](https://www.expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) St. Michaels 8.2/10 Very good (1,000 reviews) - Tranquil escape with outdoor pool near town attractions and hiking trails in St. Michaels. "Good value and close to downtown." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.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/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/7b97c3b5.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) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (874 reviews) - Quiet hotel near Chesapeake Bay offers convenient access to local attractions. "Nice staff and rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter £69 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/8e209338.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e07c03ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, pillow-top beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/d05b07bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #6, Queen with Bathtub | Egyptian cotton sheets, pillow-top beds, individually decorated](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/e0611706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Parsonage Inn [](https://www.expedia.co.uk/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) Downtown St. Michaels 9.2/10 Wonderful (131 reviews) - Stroll to historic St. Michaels attractions from this charming B&B with breakfast. "Hosts were wonderful, breakfast was delicious, everything was walkable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathaly £120 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/c982427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/8af764c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Suite | Living area | 35-inch flat-screen TV with satellite channels](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island [](https://www.expedia.co.uk/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) Tilghman 8.8/10 Excellent (92 reviews) "We were" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Guevara £131 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.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) ![Lobby](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/d0d0e0d6.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) ![Lobby](https://images.trvl-media.com/lodging/53000000/52810000/52802300/52802235/8ea761a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Microtel Inn & Suites by Wyndham Gambrills [](https://www.expedia.co.uk/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) Gambrills 9.0/10 Wonderful (1,016 reviews) - Stylish Gambrills hotel with free breakfast, near Regal Waugh Chapel and Walden Golf Club. "Great staff & clean rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmelo £71 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Gambrills-Hotels-Microtel-Inn-Suites-By-Wyndham-Gambrills.h52802235.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/65faa113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 Luxury Double, King Jacuzzi with fireplace | Premium bedding, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/aeffd976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast ](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/81d032fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/1e71523a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Brooks House B&B [](https://www.expedia.co.uk/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) St. Michaels 8.8/10 Excellent (67 reviews) "Gorgeous quaint historic house. Friendly owner, close to town " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher £137 includes taxes & fees 18 Feb - 19 Feb [](https://www.expedia.co.uk/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.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, pool 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.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1,002 reviews) - Serene bayfront escape with pool and marina views for water enthusiasts. "Staff was friendly and rooms were clean. Beautiful area to visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy £93 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/w2877h1800x0y0-f772721c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/5cc5b3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/b187b396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/60000000/59860000/59854400/59854328/42ffb5fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tilghman Island Inn [](https://www.expedia.co.uk/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information) Tilghman 9.6/10 Exceptional (121 reviews) - Waterfront escape on Maryland's beautiful Tilghman Island with seasonal pool. "Great room and water view! Staff is very friendly and welcoming. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole £129 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Tilghman-Hotels-The-Tilghman-Island-Inn.h59854328.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/391fbabf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/11cbce69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/4be52931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room | Frette Italian sheets, premium bedding, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/d6387655.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wildset [](https://www.expedia.co.uk/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) Downtown St. Michaels 9.8/10 Exceptional (417 reviews) - Unwind in a coastal hotel near Higgins Yacht Yard with complimentary treats. "Clean rooms, great staff, awesome restaurant on site called Ruse & right in downtown. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred £160 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/1000000/20000/17300/17201/c88d625f.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) ![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) ![Suite, 1 King Bed with Sofa bed, Accessible, Non Smoking | Premium bedding, pillow-top 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.co.uk/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) Bowie 9.2/10 Wonderful (1,006 reviews) - Experience a peaceful getaway at this Bowie hotel with seasonal pool and fitness centre. "Quiet lodging, great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel £82 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (959 reviews) - Serene waterfront retreat with peaceful grounds and convenient bike trail access. "Clean room, I enjoy staying here every time I'm in the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter £91 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (716 reviews) - Waterfront comfort on Kent Narrows with scenic marina views and 24-hour gym. "Amazing location and staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi J. £94 includes taxes & fees 24 Feb - 25 Feb [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/d7ca8491.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/b1c929dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom | Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate [](https://www.expedia.co.uk/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Tracys Landing 9.4/10 Exceptional (12 reviews) - Luxurious retreat with outdoor pool in Tracys Landing offers a peaceful getaway. "Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend \*\*\*\*\*" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd [](https://www.expedia.co.uk/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.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) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,001 reviews) - Experience Annapolis proximity to top attractions and Navy Academy. "The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathy £69 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/aabb28e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/9ee94703.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/180dd9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1170000/1160800/1160798/f74ef80c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Annapolis by IHG [](https://www.expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.Hotel-Information) Annapolis 8.8/10 Excellent (208 reviews) - Convenient Annapolis stay with fitness centre and access to nearby adventures. "Hotel was clean staff was friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim £67 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-Homestyle-Suites.h1160798.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) ![Lounge](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3998h2663x2y4-cd8765a0.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) ![Lobby](https://images.trvl-media.com/lodging/101000000/100980000/100975900/100975886/w3996h2664x4y0-50b1ab3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites By Marriott Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.Hotel-Information) Annapolis 8.8/10 Excellent (175 reviews) - Stylish hotel with fitness centre near Naval Academy and Annapolis attractions. "Clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £92 includes taxes & fees 22 Feb - 23 Feb [](https://www.expedia.co.uk/Annapolis-Hotels-Fairfield-Inn-Suites-By-Marriott-Annapolis.h100975886.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.co.uk/Hotel-Search?startDate=2026-03-03&endDate=2026-03-04®ionId=6264943&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=HTG_SPRING_PROMO_6264943) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FShady-Side-Hotels.d6264943.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/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 savour its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263308) ### 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. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6263322) ## Top Shady Side Hotel Reviews ![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 "The room was spotless and very quiet. " [](https://expedia.co.uk/Upper-Marlboro-Hotels-Comfort-Inn.h19389.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 "Courteous, professional staff. Clean room. Good parking. Great location within walking distance of restaurants, stores, and the State House. I would stay here again when are in Annapolis, Maryland. " [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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 staff was.very welcoming and so helpful with go to information. I have stayed their before and would again! Thankyou" [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Great hotel, across from State House. Restaurants within walking distance. Great little town, can’t wait to visit again . " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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 "Great place. Perfect." [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 "The staff were so nice and helpful and the amenities were great. The restaurant and bar were great especially the breakfast and of course the cookies. The shuttle was so convenient, fast, and super polite. Great stay. I recommend and will stay again next time I'm in town. " [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![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 "Great stay. Room was great, staff were very friendly and helpful. " [](https://expedia.co.uk/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 "Newly remodeled rooms. Very clean. Staff was so friendly and courteous! I love the fact there are two restaurants on site. " [](https://expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Clean, quiet stay." [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.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 £64 19 Feb - 20 Feb includes taxes & fees 6/10 (1,000 reviews) [](https://expedia.co.uk/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 £68 22 Feb - 23 Feb includes taxes & fees 7.6/10 Good! (1,000 reviews) [](https://expedia.co.uk/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 £71 1 Mar - 2 Mar includes taxes & fees 9/10 Wonderful! (1,012 reviews) [](https://expedia.co.uk/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 £81 1 Mar - 2 Mar includes taxes & fees 9/10 Wonderful! (1,003 reviews) [](https://expedia.co.uk/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 £82 2 Mar - 3 Mar includes taxes & fees 9/10 Wonderful! (1,002 reviews) [](https://expedia.co.uk/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 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=03%2F03%2F2026&endDate=04%2F03%2F2026&selected=10281&PinnedHotelID=10281&HadPinnedHotel=true®ionId=6264943) 8/10 Very Good! (1,000 reviews) [](https://expedia.co.uk/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ## Frequently asked questions ### What is the best area to stay in Shady Side? > This area offers immediate access to the water, which is a key reason for visiting Shady Side. You'll find properties with direct bay views, private docks, and easy access to water-based activities like fishing and boating. The main roads like Shady Side Road and Deale-Churchton Road run parallel to the water, where you'll find local seafood restaurants and small shops. > > > Families often find staying near the waterfront ideal due to the abundance of outdoor activities. Many accommodations here cater to those looking for a relaxing holiday by the water, with plenty of space for children to play and direct access to crabbing and swimming spots. > > > For couples seeking a quiet retreat, the more secluded waterfront properties offer privacy and scenic views. Imagine enjoying a sunset over the bay from your own balcony or taking a peaceful stroll along the shore. ### When is the best time to go to Shady Side? > Spring brings mild temperatures, blooming flowers, and the opportunity to enjoy outdoor activities like fishing, kayaking, and exploring the local parks without the intense heat of summer. It's a great time for couples seeking a peaceful getaway with scenic views. > > > Autumn offers comfortable temperatures and beautiful fall foliage, particularly along the waterfront. This season is ideal for those who enjoy hiking, cycling, or simply relaxing by the Chesapeake Bay. Families might appreciate the various harvest festivals and pumpkin patches in the wider area during this time. > > > While summer (June to August) is popular for its warm weather and water sports, it can be quite busy, and accommodation prices might be higher. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Shady Side hotel booking with Expedia? ### How much is the nightly rate at a Shady Side hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [Hotels near Annapolis City Dock ](https://www.expedia.co.uk/Annapolis-City-Dock-Hotels.0-l553248633992240262-0.Travel-Guide-Filter-Hotels) - [Accor Hotels in Annapolis ](https://www.expedia.co.uk/Annapolis-Hotels-Accor-Hotels.0-0-d6034082--bAccorHotels.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Annapolis ](https://www.expedia.co.uk/Annapolis-Hotels-Beach-Hotels.0-0-d6034082-tBeachHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Annapolis ](https://www.expedia.co.uk/Annapolis-Hotels-Budget-Hotels.0-0-d6034082-tBudgetHotels.Travel-Guide-Filter-Hotels) - 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