Title: 4 Stars Hotels in Shady Side, Maryland from CA $154 - Find Cheap Shady Side Hotels With 4 Stars | Expedia.ca [Shady Side Travel Guide](https://expedia.ca/Shady-Side.dx6264943)[Hotels in Shady Side](https://expedia.ca/Shady-Side-Hotels.d6264943.Travel-Guide-Hotels)[Vacation Rentals in Shady Side](https://expedia.ca/Shady-Side-Vacation-Rentals.d6264943.Travel-Guide-VacationRentals)[Flights to Shady Side](https://expedia.ca/Cheap-Flights-To-Shady-Side.d6264943.Travel-Guide-Flights)[Shady Side Car Rentals](https://expedia.ca/Car-Rentals-In-Shady-Side.d6264943.Car-Rental-Guide)[Shady Side Vacation Packages](https://expedia.ca/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) # 4 Stars Hotels in Shady Side, Maryland from CA $154 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](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 [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-25&endDate=2025-10-26&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-26&endDate=2025-10-27&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-11-07&endDate=2025-11-09&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shady Side 4 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8.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) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/adcfc6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/53807244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Largo/Washington DC Upper Marlboro 8.0/10 Very good (1009) "Our room was nice and clean and the bed was very comfortable, very good selection for breakfast, the staff was very friendly..we will stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $150 CA $169 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/900/846/4033d0a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis Annapolis 9.4/10 Exceptional (1018) "Staff was outstanding!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred CA $197 CA $224 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/5575a0f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/1000000/10000/3100/3040/3952dad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis Annapolis 8.6/10 Excellent (1006) "Comfortable place to stay, nice shopping area close by. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roya CA $135 CA $154 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![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/2000000/1680000/1678800/1678710/768e2886.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) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/67adefe8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Annapolis Annapolis 8.6/10 Excellent (1002) "The friendly and helpful staff made our stay enjoyable. We were out with friends most of the time, so mainly appreciated having a comfortable place to spend nights." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $223 CA $254 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking, Balcony](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, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (872) "Clean room. Friendly staff awesome location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent CA $284 CA $324 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.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) ![Marina](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/27bb8cb0.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/2000000/1060000/1050500/1050433/ad8d4ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort Chesapeake Beach 8.4/10 Very good (1002) "Our stay was great! No complaints at all." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $137 CA $181 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.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) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/d2860230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (423) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery CA $271 CA $337 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d0af41e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/ffb9b376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/3e21912d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### The Oaks Waterfront Easton 10/10 Exceptional (39) "Loved the Oaks! Fabulous accommodations and excellent staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $578 CA $636 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![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) ![Luxury Suite, Garden View | Private kitchen](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/c6a32c3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Family House](https://images.trvl-media.com/lodging/115000000/114880000/114870700/114870697/48995b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Legacy Villa Upper Marlboro CA $231 CA $262 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/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.ca/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.ca/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/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Inn at Perry Cabin 308 Watkins Ln, St. Michaels, MD CA $566 CA $684 total Nov 3 - Nov 4 includes taxes & fees 9.4/10 Exceptional! (367 reviews) [](https://expedia.ca/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/ad846553_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Tacaro Estate 6220 Town Point Rd, Tracys Landing, MD CA $497 CA $567 total Oct 27 - Oct 28 includes taxes & fees 9.2/10 Wonderful! (10 reviews) [](https://expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=6264943&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=6264943&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=6264943&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=6264943&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®ionId=6264943&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=27%2F10%2F2025&endDate=28%2F10%2F2025®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](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were exceedingly helpful and friendly. Parking was close and easy." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Wonderfully. We were pleasantly surprised at the hotel. Very nice. Well decorated. Convenient and walkable location. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![DoubleTree by Hilton Hotel Largo/Washington DC](//images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg) ### DoubleTree by Hilton Hotel Largo/Washington DC 10/10 Excellent "Staff was the best! " [](https://expedia.ca/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Clean room. Friendly staff awesome location. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ## Find out more about Shady Side If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Shady Side are calling your name. Known for providing first-rate service in amazing locations, each of the Shady Side 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Shady Side. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Shady Side, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Shady Side hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Shady Side? > To find a 4-star hotel in Shady Side that matches your budget, use Expedia's filter tool. Check out the available options during your travel dates and use our pricing filter to set your limit. You can also sort your results by the most affordable stay first. > > > > - Search for the lowest price from CA $567 ### What's the difference between 5-star and 4-star hotels in Shady Side? > If you choose to book a stay at a 4-star hotel in Shady Side, you'll usually find loads of amenities to ensure you're relaxed, such as a restaurant, gym and pool. You can enjoy top-quality service and upmarket surroundings. Opt for a 5-star hotel and you'll get a few extra bells and whistles — think around-the-clock concierge, on-site spas and nightly turndown services. You're likely to get additional amenities and exclusive services at a 5-star stay, though both are fabulous options for luxury travellers. ### Does Shady Side have any 4-star all-inclusive resorts? > Enjoy a relaxing vacation experience where just about everything is included in the one rate by using our "All inclusive" filter. Keeping to your budget is a breeze when your meals, accommodations and activities are already taken care of. Eager for more ideas? 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