Title: TOP Historic Hotels in Kent Island, MD for 2026 | 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) ![Beautiful summer sunset over the Chesapeake bay. ](https://images.trvl-media.com/place/553248635077608788/4fcd43d4-cd30-434c-8826-71e72aed3588.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jennifer Crim # Search Historic Hotels in Kent Island - ![](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 Historic Hotels Tonight [14 Dec - 15 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [15 Dec - 16 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Kent Island historic hotels ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/18961763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed (Safari Suite (at Tidewater House)) | Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tidewater Inn [](https://www.expedia.co.uk/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) Easton 8.8/10 Excellent (842) "Friendly staff, spotless room, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven £147 includes taxes & fees 1 Jan - 2 Jan 2026 [](https://www.expedia.co.uk/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/c982427d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/8af764c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/6e7f4df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0efeb5e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island [](https://www.expedia.co.uk/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) Tilghman 8.8/10 Excellent (90) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne £144 includes taxes & fees 1 Jan - 2 Jan 2026 [](https://www.expedia.co.uk/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d0edf916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/c0808af9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/b40492dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/e5b3706d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants [](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) North Beach 10/10 Exceptional (31) "Perfect place to spend quality time with our three adult children and their significant others. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malarkey F. £304 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c4f67dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) Historic District 9.0/10 Wonderful (1901) "Great staff, comfortable beds, clean rooms and perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn [](https://www.expedia.co.uk/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District 9.4/10 Exceptional (83) "The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth £163 includes taxes & fees 16 Dec - 17 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/1976e6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast ](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/03fed2cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/2624f48e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/3b6079a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel [](https://www.expedia.co.uk/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) Annapolis 9.8/10 Exceptional (31) "Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ian [](https://www.expedia.co.uk/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/8d2066be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/97119172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel [](https://www.expedia.co.uk/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) Historic District 10/10 Exceptional (3) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Jo £275 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/1aa587de_edited_b1ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-7a94439d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y2-e4e5546a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1514h908x8y2-08d635bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA! [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-1-Block-From-Gate-1-At-USNA.h117588789.Hotel-Information) Historic District 10/10 Exceptional (5) "Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie S. £537 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-1-Block-From-Gate-1-At-USNA.h117588789.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/18f7d789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/528b087a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/708c7c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76580000/76579700/76579660/42aee333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Downtown 3rd Floor 1 Bedroom Apt [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.Hotel-Information) Historic District 9.8/10 Exceptional (19) "We had a great time staying that this home. It was a perfect stay for my wife and I." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric S. £213 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-Downtown-3rd-Floor-1-Bedroom-Apt.h76579660.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/c5b533c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/7d0396b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/46ad9c59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/4d32484b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home in Downtown Annapolis [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) Historic District £527 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.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=2025-12-28&endDate=2025-12-29®ionId=553248635077608788&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Kent Island Hotel Reviews ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "Yes it was" [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Crowne Plaza Annapolis by IHG](https://images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "This is a very nice hotel clean and seems to be new" [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](https://images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Very clean and quiet! Convenient to downtown Annapolis and many great restaurants! Parking behind the building is also a plus!" [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Fantastic hotel and they upgraded us to a room with a stunning view!" [](https://expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](https://images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet." [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent" [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "Spectacular " [](https://expedia.co.uk/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) ### Graduate by Hilton Annapolis 10/10 Excellent "Very nice hotel. The dog park could have better lighting. " [](https://expedia.co.uk/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "This is by far the best hotel we have stayed in! It was convenient in many ways, plus the breakfast was a great start to the day! We will be coming back again, thank you! 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