Title: TOP Luxury Hotels in Kent Island, MD for 2026 - Kent Island Upscale Hotels | Expedia.co.uk [Kent Island Travel Guide](https://expedia.co.uk/Kent-Island.dx553248635077608788)[Hotels in Kent Island](https://expedia.co.uk/Kent-Island-Hotels.d553248635077608788.Travel-Guide-Hotels)[Holiday Rentals in Kent Island](https://expedia.co.uk/Kent-Island-Holiday-Rentals.d553248635077608788.Travel-Guide-HolidayRentals)[Flights to Kent Island](https://expedia.co.uk/Cheap-Flights-To-Kent-Island.d553248635077608788.Travel-Guide-Flights)[Kent Island Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Kent-Island.d553248635077608788.Car-Hire-Guide)[Kent Island Holidays](https://expedia.co.uk/Kent-Island.d553248635077608788.Holidays-City-Breaks) ![The Bay Bridge from Kent Island, MD.](https://images.trvl-media.com/place/553248635077608788/19706092-2390-4974-ae30-e0221b2879a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635077608788/19706092-2390-4974-ae30-e0221b2879a3.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/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 Kent Island Luxury Hotels Tonight [30 Mar - 31 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2026-03-30&endDate=2026-03-31&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [31 Mar - 1 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2026-03-31&endDate=2026-04-01&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2026-04-03&endDate=2026-04-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2026-04-10&endDate=2026-04-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Kent Island luxury hotels ![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) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room | Frette Italian sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (442 reviews) "Very clean room, staff was very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Byron £175 includes taxes & fees 2 Apr - 3 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/43373394.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) ![Hair salon](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/45498263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort [](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) Chesapeake Beach 8.4/10 Very good (1,008 reviews) "Great place to stay with lovely views" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David £129 includes taxes & fees 16 Apr - 17 Apr [](https://www.expedia.co.uk/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/6a67d68d.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) ![Luxury Suite, 1 Bedroom | Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down duvets](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.co.uk/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 £222 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![Premium bedding, down duvets, 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) ![Fireplace](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/7a7c860e.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) ![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 [](https://www.expedia.co.uk/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) Downtown St. Michaels 9.6/10 Exceptional (376 reviews) "Fantastic - loved our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily £474 includes taxes & fees 19 Apr - 20 Apr [](https://www.expedia.co.uk/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/c21b600a.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) ![Garden](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) Annapolis 8.6/10 Excellent (1,004 reviews) "Wonderful and clean accommodations " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily £77 includes taxes & fees 6 Apr - 7 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![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) ![Indoor wedding](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/d1a8f617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom, Balcony | Balcony view](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/1f0e0a5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/2000000/1730000/1721600/1721586/6aa17d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oaks Waterfront [](https://www.expedia.co.uk/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) Easton 10/10 Exceptional (41 reviews) "Staff, breakfast, and room were all superb!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey £365 includes taxes & fees 31 Mar - 1 Apr [](https://www.expedia.co.uk/Easton-Hotels-The-Oaks-Waterfront-Inn.h1721586.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/73550aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/96f9cffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed, City View | Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/c301dc98.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) ### The Westin Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Annapolis 8.8/10 Excellent (1,001 reviews) "We were given a beautiful upgrade to a very bright room with double windows. Enjoyable stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janet £154 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/76a0c2be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/4dba2228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/fb8e8cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) Historic District 8.8/10 Excellent (914 reviews) "I would have given an excellent but there was still some renovations being done. Staff was great, rooms were beautiful and clean. Location is perfect and within walking distance to tons of shops, restaurants and bars. Their restaurant was currently closed for remodeling but guests can still get room service from the restaurant next door. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Autumn £231 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/1000000/10000/900/846/9175a19d.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) Annapolis 9.4/10 Exceptional (1,003 reviews) "The brunch setting and setup looked amazing. Sadly, we had plans to eat in DTA and didn’t get to experience the brunch. The vibes of the hotel, the attentive staff, and the housekeeping was top notch. We are returning to stay again for commissioning week!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly K £170 includes taxes & fees 5 Apr - 6 Apr [](https://www.expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-04-13&endDate=2026-04-14®ionId=553248635077608788&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Find out more about Kent Island ### Kent Islandand its attractions for luxury travelers For discerning travellers seeking a luxurious getaway, Kent Island offers a delightful blend of natural beauty and refined experiences. Begin your journey at the iconic Kent Island Yacht Club, where you can enjoy exquisite dining with stunning waterfront views and perhaps even a sailing adventure on the Chesapeake Bay. For a touch of history, explore the charming town of Stevensville, where the picturesque landscapes and historic sites like the Old Stevensville Historic District provide a quaint yet upscale atmosphere. Nature enthusiasts will relish a visit to the Chesapeake Bay Environmental Center, where guided eco-tours offer an intimate glimpse into the region's diverse wildlife and ecosystems. Golf aficionados can tee off at the exclusive Queenstown Harbor, featuring meticulously maintained courses that promise a day of leisure and sport. As you indulge in these attractions, consider staying at the luxurious Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, where you can unwind in elegant rooms, pamper yourself at the full-service spa, and enjoy fine dining experiences, all while soaking in breathtaking views of the water. This blend of adventure, relaxation, and top-tier service ensures that your stay on Kent Island is not just memorable, but truly exceptional. ## Top Kent Island Hotel Reviews ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "The brunch setting and setup looked amazing. Sadly, we had plans to eat in DTA and didn’t get to experience the brunch. The vibes of the hotel, the attentive staff, and the housekeeping was top notch. We are returning to stay again for commissioning week!" [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Historic charm, lovely location, friendly, helpful staff." [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/be920909_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Everything was great had dinner in the room and it arrived timely and room was clean and very comfortable beds. I just couldn’t say enough maid service was great as well. " [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/65a79802_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "I will be back" [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/0f404f98_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Location great . Hotel impressive for the cost. " [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/8ee1610f_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Great location & service was wonderful." 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