Title: The Best 5 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 5 Star Hotels Tonight [Mar 5 - Mar 6](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-05&endDate=2026-03-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 6 - Mar 7](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-06&endDate=2026-03-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-06&endDate=2026-03-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6264943&startDate=2026-03-13&endDate=2026-03-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Shady Side 5-star hotels ![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/12b2f8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/4ea15d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/7a7c860e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin [](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) Downtown St. Michaels 9.6/10 Exceptional (374 reviews) "Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph $371 nightly $408 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/5726b171.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 comforters](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/b1c929dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate [](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) Tracys Landing 9.4/10 Exceptional (12 reviews) "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 $367 nightly $418 total Mar 9 - Mar 10 Total with taxes and fees [](https://www.expedia.com/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.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%2F5Star-Shady-Side-Hotels.s50-0-d6264943.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Shady-Side-Hotels.s50-0-d6264943.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Shady Side. ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court Annapolis MD $89 nightly $102 total Mar 8 - Mar 9 Total with taxes and fees 8.6/10 Excellent! (1,013 reviews) [](https://expedia.com/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Graduate by Hilton Annapolis 126 West St Annapolis MD $166 nightly $190 total Mar 22 - Mar 23 Total with taxes and fees 9.4/10 Exceptional! (1,001 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Annapolis Waterfront Hotel, Autograph Collection 80 Compromise St Annapolis MD $212 nightly $241 total Mar 29 - Mar 30 Total with taxes and fees 8.8/10 Excellent! (906 reviews) [](https://expedia.com/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=6264943&star=50&star=50&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 ## Find out more about Shady Side Why not request total luxury on your trip to Shady Side? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Shady Side so popular in the last year. There's no reason to delay a getaway to Shady Side any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Reserve one of our 5-star hotels in Shady Side and indulge in the finer things in life for a while. What are you waiting for? ### 5-Star Hotels in Shady Side You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and attentive guest service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A mud wrap treatment that will leave you feeling refreshed and alive? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A Swedish massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. But you aren't going to spend your entire vacation in your room, of course. You're in luck. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Shady Side are waiting for you to relax after an exciting day. ### Your Getaway Starts Today The results are in, and Shady Side 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Opt for one of Expedia's Shady Side 5-star hotels today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Shady Side? > - Search for the lowest price per night from $102 ### What makes a hotel 5 stars in Shady Side? ### Are there any 5-star all-inclusive resorts in Shady Side? ## 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) - [5 Star Hotels in Galesville ](https://www.expedia.com/5Star-Galesville-Hotels.s50-0-d6264947.Travel-Guide-Filter-Hotels) - 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