Title: The Best 4 Star Hotels in Shady Side, MD from $102 | 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 4 Star Hotels Tonight [Mar 28 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-28&endDate=2026-03-29&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 29 - Mar 30](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-29&endDate=2026-03-30&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-04-10&endDate=2026-04-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side 4-star hotels ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/900/846/9175a19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/48975360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis [](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 9.4/10 Exceptional (1,002 reviews) "Central l9cation, easy walk to all sites." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $175 nightly $199 total Apr 19 - Apr 20 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/adcfc6e9.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) ### 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 (1,004 reviews) "Comfy beds...excellent showers." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shawnna $114 nightly $129 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed | Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony | Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District 8.8/10 Excellent (912 reviews) "I would have given an excellent but there was still some renovations being done. Staff was great, rooms were beautiful and clean. Location is perfect and within walking distance to tons of shops, restaurants and bars. Their restaurant was currently closed for remodeling but guests can still get room service from the restaurant next door. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Autumn $229 nightly $261 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/d4b92367.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) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,001 reviews) "Wonderful and clean accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily $89 nightly $102 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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) ![Hair salon](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/45498263.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) ### 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 (1,004 reviews) "Great place to stay with lovely views" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $133 nightly $146 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner and brunch served](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/0684bd50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis [](https://www.expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Annapolis 8.8/10 Excellent (1,000 reviews) "We were given a beautiful upgrade to a very bright room with double windows. Enjoyable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet $179 nightly $204 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room in the Barn | Frette Italian sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.com/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (442 reviews) "Very clean room, staff was very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Byron $189 nightly $210 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/18678d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Cottage, 1 King Bed, River View | Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/c5479a6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/6aa17d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront [](https://www.expedia.com/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Easton 10/10 Exceptional (41 reviews) "Staff, breakfast, and room were all superb!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey $489 nightly $538 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Family House | In-room dining](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/49f997cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/d716dd8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Room, 3 Bedrooms, Pool View | In-room dining](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/94666622.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/40258b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Villa [](https://www.expedia.com/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.Hotel-Information) Upper Marlboro [](https://www.expedia.com/Upper-Marlboro-Hotels-Legacy-Villa.h114870697.Hotel-Information) ![](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%2F4Star-Shady-Side-Hotels.s40-0-d6264943.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Shady-Side-Hotels.s40-0-d6264943.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shady Side. ![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at Perry Cabin 308 Watkins Ln St. Michaels MD $615 nightly $677 total Apr 5 - Apr 6 Total with taxes and fees 9.6/10 Exceptional! (375 reviews) [](https://expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![The Inn at Tacaro Estate](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Tacaro Estate 6220 Town Point Rd Tracys Landing MD $259 nightly $295 total Apr 23 - Apr 24 Total with taxes and fees [](https://expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Still don't see what you're looking for? [See all properties in Shady Side.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40&star=40&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6264943&star=40&star=40&amenities=WATER_PARK) 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. ## 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 "Julie is amazing!" [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg) ### Rod 'N' Reel Resort 10/10 Excellent "Very nice hotel. " [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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 "Unique hotel in the heart of Annapolis. The room was lovely, comfortable and well equipped. Parking was a bit expensive $32 one day and strange, couldnt actually park in the covered garrage that was only for vallette patrons. Would have been nice to have a regular coffee maker in the room, only instant coffee was on offer. " [](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 10/10 Excellent "Clean room. Friendly staff." [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg) ### The Westin Annapolis 10/10 Excellent "We were given a beautiful upgrade to a very bright room with double windows. Enjoyable stay." [](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 8/10 Good "I would have given an excellent but there was still some renovations being done. Staff was great, rooms were beautiful and clean. Location is perfect and within walking distance to tons of shops, restaurants and bars. Their restaurant was currently closed for remodeling but guests can still get room service from the restaurant next door. " [](https://expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ## Find out more about Shady Side ## Shady Side Four Star Hotel Information When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Shady Side, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Shady Side 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service. Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Shady Side. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Shady Side, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop. Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Shady Side hotels offer everything your heart desires. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Shady Side? > - Search for the lowest price from $295 ### What's the difference between 5-star and 4-star hotels in Shady Side? ### Does Shady Side have any 4-star all-inclusive resorts? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [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) - [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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