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 19 - Mar 20](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-19&endDate=2026-03-20&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 20 - Mar 21](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-20&endDate=2026-03-21&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-27&endDate=2026-03-29&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/1000000/10000/900/846/48975360.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.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) ### Graduate by Hilton Annapolis [](https://www.expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 9.4/10 Exceptional (1,003 reviews) "Central l9cation, easy walk to all sites." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James $171 nightly $195 total Mar 29 - Mar 30 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) ![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) ![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) ![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 (1,002 reviews) "Room was very cleaned and full of the room amenities for you to enjoy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicole $106 nightly $120 total Apr 5 - Apr 6 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, 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) ![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) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District 8.8/10 Excellent (909 reviews) "We liked it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emmy $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) ![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.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,002 reviews) "Very courteous staff. Beds were amazing. Nice meeting rooms and gym. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim $89 nightly $102 total Mar 29 - Mar 30 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) ![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) ![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) ### 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 (1,001 reviews) "Everything was great đź‘Ť " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Reginald $128 nightly $140 total Mar 31 - Apr 1 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) ![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) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.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 (1,002 reviews) "Great property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Darryl $179 nightly $204 total Mar 27 - Mar 28 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) ![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) ![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.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 (441 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) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom, Balcony | Balcony view](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/1f0e0a5a.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) ### 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 $440 nightly $484 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/115000000/114880000/114870700/114870697/40258b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, blender, toaster oven, waffle maker](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/1eac847e.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) ### 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 $371 nightly $408 total Mar 24 - Mar 25 Total with taxes and fees 9.6/10 Exceptional! (374 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 $281 nightly $321 total Mar 25 - Mar 26 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%2F20%2F2026&endDate=3%2F21%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%2F20%2F2026&endDate=3%2F21%2F2026®ionId=6264943&star=40&star=40&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%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%2F20%2F2026&endDate=3%2F21%2F2026®ionId=6264943&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=6264943&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F20%2F2026&endDate=3%2F21%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 ![Rod 'N' Reel Resort](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394_y.jpg) ### Rod 'N' Reel Resort 2/10 Terrible "Bathroom door wouldn't close, laminate floor was popping up, no microwave in the room, fire alarm going off early in the morning, construction happening early in the morning. I've stayed at Super 8s and Motel 6s that have been better than this. It is a cheap hotel that is overpriced because you can see water from it and there are no other options nearby." [](https://expedia.com/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 8/10 Good "not fas tinternet" [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 "Comfy beds...excellent showers." [](https://expedia.com/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.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 "The hotel has cute and trendy decor. It’s located centrally nearby many restaurants and coffee shops around. Our room was clean and spacious. Check in was easy and on point. We had no issues with this hotel. This is my second Graduate hotel that I’m staying in and they are very efficient. " [](https://expedia.com/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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 10/10 Excellent "Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open." [](https://expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf_y.jpg) ### The Westin Annapolis 10/10 Excellent "Clean Room, quiet nights sleep in comfortable bed. Shower was awesome (Water Pressure A+). Friendly staff, and bar staff at night were very friendly and accommodating." [](https://expedia.com/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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 $321 ### 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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