Title: 5 Stars Hotels in Shady Side, Maryland from CA $170 - Find Cheap Shady Side Hotels With 5 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://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Shady Side, Maryland from CA $170 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-09-29&endDate=2025-09-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-09-30&endDate=2025-10-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6264943&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Shady Side 5 Star Hotels ![Breakfast, lunch, dinner served; ocean views](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/3dd4d01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/2de6ebed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin St. Michaels 9.6/10 Exceptional (364) "Beautiful place to stay." CA $740 CA $895 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Horseback riding](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Room, Bay View](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/aa3e4df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ed0e25a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/57a2b6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (9) "It was perfect!! We had a great stay. Luca was so kind and attentive. The property is astonishing. Perfect weekend retreat! Thank you so much " CA $531 CA $606 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/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.ca/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.ca/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 Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/aa92a5c8_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Largo/Washington DC 9100 Basil Court, Upper Marlboro, MD CA $150 CA $170 total Oct 16 - Oct 17 includes taxes & fees 7.8/10 Good! (1,019 reviews) [](https://expedia.ca/Waldorf-Hotels-DoubleTree-By-Hilton-Hotel-Largo-Washington-DC.h21463.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court, Annapolis, MD CA $156 CA $178 total Oct 20 - Oct 21 includes taxes & fees 8.6/10 Excellent! (1,015 reviews) [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Annapolis 100 Westgate Cir, Annapolis, MD CA $298 CA $340 total Oct 26 - Oct 27 includes taxes & fees 8.6/10 Excellent! (1,006 reviews) [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.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=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=6264943&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=6264943&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=6264943&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=6264943&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®ionId=6264943&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=30%2F09%2F2025&endDate=01%2F10%2F2025®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 ## Five Star Hotels in Shady Side There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Shady Side so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Shady Side and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Shady Side Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Shady Side The results are in, and Shady Side 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Shady Side! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Shady Side 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? > You can find many different pricing options for 5-star hotels in Shady Side on Expedia. How much you'll pay will depend on when you want to travel, trip length and other factors. Compare all of the available properties for your desired dates and use our pricing and other filters to find the perfect luxury stay. > > > > - Search for the lowest price per night from CA $170 ### What makes a hotel 5 stars in Shady Side? > From gourmet dining venues and fitness centres to pools and luxury bedding, the 5-star experience in Shady Side is all about luxury and relaxation. But it takes more than just upscale amenities to earn a 5-star rating. Accommodations must also deliver extraordinary guest-centric services like in-room massages, laundry and dry cleaning and 24-hour room service. ### Are there any 5-star all-inclusive resorts in Shady Side? > Use our filter tool to find an upscale getaway in Shady Side where most of what you need is included. From there, narrow down your results for hotels that have 5 stars and are deemed "All inclusive." The main thing on the agenda at these stays? 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[Edgewater Vacation Rentals](https://www.expedia.ca/Edgewater-Vacation-Rentals.d6348965.Travel-Guide-VacationRentals) - [Things to do in Edgewater](https://www.expedia.ca/Things-To-Do-In-Edgewater.d6348965.Travel-Guide-Activities) - [Book 5 Star Hotels in Shady Side on Expedia.com](https://www.expedia.com/5Star-Shady-Side-Hotels.s50-0-d6264943.Travel-Guide-Filter-Hotels)