Title: 5 Stars Hotels in Sherwood, Maryland from CA $169 - Find Cheap Sherwood Hotels With 5 Stars | Expedia.ca [Sherwood Travel Guide](https://expedia.ca/Sherwood.dx6034722)[Hotels in Sherwood](https://expedia.ca/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)[Vacation Rentals in Sherwood](https://expedia.ca/Sherwood-Vacation-Rentals.d6034722.Travel-Guide-VacationRentals)[Flights to Sherwood](https://expedia.ca/Cheap-Flights-To-Sherwood.d6034722.Travel-Guide-Flights)[Sherwood Car Rentals](https://expedia.ca/Car-Rentals-In-Sherwood.d6034722.Car-Rental-Guide)[Sherwood Vacation Packages](https://expedia.ca/Sherwood.d6034722.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 Sherwood, Maryland from CA $169 ![](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 Sherwood 5 Star Hotels Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-11&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-12&endDate=2025-10-13&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sherwood 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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/3dd4d01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Garden View | Garden view](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/b1a0ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin St. Michaels 9.6/10 Exceptional (365) "Beautiful place to stay." CA $566 CA $685 total includes taxes & fees Nov 12 - Nov 13 [](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 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) ![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) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "Amazing hospitality " CA $568 CA $648 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![Dinner served](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/be8a1621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/20605cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/625fcac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/w264h344x4y2-b20fcf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at 202 Dover Easton 10/10 Exceptional (14) "Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience." [](https://www.expedia.ca/Easton-Hotels-Inn-At-202-Dover.h5308723.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-Sherwood-Hotels.s50-0-d6034722.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Sherwood-Hotels.s50-0-d6034722.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 Sherwood. ![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 $148 CA $169 total Nov 3 - Nov 4 includes taxes & fees 8.6/10 Excellent! (1,014 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 $273 CA $311 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (1,001 reviews) [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Hyatt Regency Chesapeake Bay](https://images.trvl-media.com/lodging/1000000/900000/890500/890486/6000a351_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Chesapeake Bay 100 Heron Blvd, Cambridge, MD CA $268 CA $371 total Oct 13 - Oct 14 includes taxes & fees 8.6/10 Excellent! (1,004 reviews) [](https://expedia.ca/Cambridge-Hotels-Hyatt-Regency-Chesapeake-Bay.h890486.Hotel-Information) Still don't see what you're looking for? [See all properties in Sherwood.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&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=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=13%2F10%2F2025&endDate=14%2F10%2F2025®ionId=6034722&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 Sherwood Hotel Reviews ## Find out more about Sherwood ## Five Star Hotels in Sherwood 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 Sherwood 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 Sherwood and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Sherwood 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 Sherwood The results are in, and Sherwood 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 Sherwood! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Sherwood today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in Sherwood? > Offering premium amenities and services, Expedia travellers rate [Inn at Perry Cabin](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) as one of the most popular 5-star hotels in Sherwood. You'll be in the lap of luxury from the minute you arrive. ### How much does it cost to stay in a 5-star hotel in Sherwood? > The amount you pay for a 5-star hotel in Sherwood depends on factors like when you plan to go and the length of your stay. Our insider tip for bagging an awesome deal? Use our pricing filters to check out all of the available hotels for your chosen dates. > > > > - Search for the lowest price per night from CA $169 ### What makes a hotel 5 stars in Sherwood? > In Sherwood, a hotel must offer a specific number of high-end amenities to be rated 5 stars. These may include on-site gyms, saunas and spas, gourmet restaurants, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-focused standard of service. You can expect things like in-room massages, nightly turn-down services and concierge services. 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