Title: 5 Stars Hotels in Kent Island, Maryland from CA $169 - Find Cheap Kent Island Hotels With 5 Stars | Expedia.ca [Kent Island Travel Guide](https://expedia.ca/Kent-Island.dx553248635077608788)[Hotels in Kent Island](https://expedia.ca/Kent-Island-Hotels.d553248635077608788.Travel-Guide-Hotels)[Vacation Rentals in Kent Island](https://expedia.ca/Kent-Island-Vacation-Rentals.d553248635077608788.Travel-Guide-VacationRentals)[Flights to Kent Island](https://expedia.ca/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)[Kent Island Car Rentals](https://expedia.ca/Car-Rentals-In-Kent-Island.d553248635077608788.Car-Rental-Guide)[Kent Island Vacation Packages](https://expedia.ca/Kent-Island.d553248635077608788.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/43a9579ca6b27aad6faa82d08f434807.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jennifer Crim # 5 Stars Hotels in Kent Island, 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 Kent Island 5 Star Hotels Tonight [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-09&endDate=2025-10-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-10&endDate=2025-10-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kent Island 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) ![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) ![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 (365) "Beautiful place to stay." CA $596 CA $722 total includes taxes & fees Oct 15 - Oct 16 [](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) ![Luxury Suite, 1 Bedroom](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "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 $566 CA $645 total includes taxes & fees Oct 12 - Oct 13 [](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) ![Room](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/82384fab.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) ![Exterior](https://images.trvl-media.com/lodging/6000000/5310000/5308800/5308723/625fcac5.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-Kent-Island-Hotels.s50-0-d553248635077608788.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Kent-Island-Hotels.s50-0-d553248635077608788.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 Kent Island. ![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! (1,001 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 $272 CA $310 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) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Graduate by Hilton Annapolis 126 West St, Annapolis, MD CA $256 CA $291 total Oct 30 - Oct 31 includes taxes & fees 9.2/10 Wonderful! (1,004 reviews) [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Still don't see what you're looking for? [See all properties in Kent Island.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&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=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635077608788&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. ## Learn more about Kent Island Cross the Chesapeake Bay Bridge to discover Kent Island's scenic waterfront and fresh seafood restaurants. Kayak through tranquil creeks, cycle the Cross Island Trail, or visit historic Stevensville for a taste of Eastern Shore charm. [See all hotels in Kent Island](https://www.expedia.ca/Hotel-Search?startDate=2025-10-23&endDate=2025-10-24&adults=2®ionId=553248635077608788) ![](https://mediaim.expedia.com/destination/2/43a9579ca6b27aad6faa82d08f434807.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Jennifer Crim ## Top Kent Island Hotel Reviews ## Find out more about Kent Island Luxury is the name of the game at the best 5 Stars hotels in Kent Island. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Kent Island 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Kent Island hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Kent Island without giving up even an inch of quality. 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