Title: The Best Shady Side Hotels with Pools from $108 - Hotels with indoor pools in Shady Side, MD | Expedia.com [Shady Side Travel Guide](https://expedia.com/Shady-Side.dx6264943)[Hotels in Shady Side](https://expedia.com/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.com/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.com/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Car Rentals in Shady Side](https://expedia.com/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.com/Shady-Side.d6264943.Destination-Travel-Guides) ![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 ## Check availability on Shady Side Hotels with a Pool Tonight [Apr 3 - Apr 4](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-03&endDate=2026-04-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Apr 4 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-04&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-03&endDate=2026-04-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-10&endDate=2026-04-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side hotels with a pool ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.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) ![Standard Single Room, 1 King Bed | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.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 (135 reviews) - Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge. $149 nightly $162 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.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.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (887 reviews) - Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay. $98 nightly $108 total Apr 15 - Apr 16 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/6e7f4df6.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) ![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) ### Wylder Tilghman Island [](https://www.expedia.com/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) Tilghman 8.8/10 Excellent (94 reviews) - Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna. $156 nightly $171 total Apr 27 - Apr 28 Total with taxes and fees [](https://www.expedia.com/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.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) ![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.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very Good (1,001 reviews) - Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary. $99 nightly $110 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/67743db3.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) ![Terrace/patio](https://images.trvl-media.com/lodging/10000000/9330000/9323700/9323601/d898936b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Knapps Narrows Marina & Inn [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.Hotel-Information) Sherwood 9.4/10 Exceptional (377 reviews) - Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures. $150 nightly $165 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Tilghman-Hotels-Knapps-Narrows-Marina-Inn.h9323601.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) ![Front of property](https://images.trvl-media.com/lodging/17000000/16720000/16714500/16714441/6594eb94.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) ### George Brooks House B&B [](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) St. Michaels 8.8/10 Excellent (70 reviews) - Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance. $170 nightly $187 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-George-Brooks-House-BB.h16714441.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/16000000/15610000/15604200/15604114/06cdc3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (478 reviews) - Pool paradise meets scenic marina views for a refreshing escape on the water. $152 nightly $173 total Apr 7 - Apr 8 Total with taxes and fees [](https://www.expedia.com/Deale-Hotels-Anchored-Inn-At-Hidden-Harbour-Marina.h15604114.Hotel-Information) ![Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/9f6ae80a.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) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.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) ### 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 (1,005 reviews) - Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort. $155 nightly $170 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/97d2d16a.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (977 reviews) - Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers. $116 nightly $129 total Apr 16 - Apr 17 Total with taxes and fees [](https://www.expedia.com/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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) ![Room #6, Queen with Bathtub | Egyptian cotton sheets, pillowtop 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) ![Luxury Suite, 2 Bedrooms, Balcony | Room amenity](https://images.trvl-media.com/lodging/2000000/1600000/1592000/1591926/23007304.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) ### Parsonage Inn [](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.Hotel-Information) Downtown St. Michaels 9.2/10 Wonderful (131 reviews) - Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons. $169 nightly $186 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-Parsonage-Inn.h1591926.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=2026-04-18&endDate=2026-04-19®ionId=6264943&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Shady Side Breakfast included 4 stars 5 stars Hot tub Spa ## Top Shady Side Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Great location, friendly staff and clean rooms" [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "I love it here" [](https://expedia.com/Upper-Marlboro-Hotels-Comfort-Inn.h19389.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 6/10 Okay "Rooms are clean. Pillows were not comfortable. Pool needs cleaning; hot tub wasn’t working. Overall ok stay." [](https://expedia.com/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Very clean and spacious room. Excellent service" [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 8/10 Good "I didn't eat there " [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/eac8c079_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "It was a nice and peaceful stay, and I was able to bring my dog along for the weekend trip!" [](https://expedia.com/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](https://images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent "Lovely place. Annapolis is a beautiful city. Great restaurants and shopping. This was by far the best hotel we stayed in our whole trip. " [](https://expedia.com/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway](https://images.trvl-media.com/lodging/1000000/10000/6400/6366/c4bcae00_y.jpg) ### La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway 10/10 Excellent "Great location " [](https://expedia.com/College-Park-Hotels-La-Quinta-Inn-Suites-By-Wyndham-DC-Metro-Capital-Beltway.h6366.Hotel-Information) ![Holiday Inn Express I-95 Capitol Beltway-Largo by IHG](https://images.trvl-media.com/lodging/2000000/1360000/1357100/1357084/fb2063de_y.jpg) ### Holiday Inn Express I-95 Capitol Beltway-Largo by IHG 6/10 Okay "The price I paid was to high for the hotel conditions " [](https://expedia.com/Waldorf-Hotels-Holiday-Inn-Express-I-95-Capitol-Beltway-Largo.h1357084.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Shady Side? ### What is there to see and do in Shady Side? ### When is the best time to book a hotel with a pool in Shady Side? ## Explore a world of travel with Expedia - 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