Title: TOP Historic Hotels in Kent Island, MD for 2025 | 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) ![](https://mediaim.expedia.com/destination/2/43a9579ca6b27aad6faa82d08f434807.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 [28 Oct - 29 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [29 Oct - 30 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [31 Oct - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635077608788&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Kent Island Historic Hotels ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/937d59ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Widows Walk Suite | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/ba45b764.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) ![Waterfront Suite | Living area | 35-inch flat-screen TV with satellite channels](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Tilghman Island Tilghman 8.8/10 Excellent (87) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne £167 includes taxes & fees 21 Nov - 22 Nov [](https://www.expedia.co.uk/Tilghman-Hotels-Wylder-Tilghman-Island.h102610148.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.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) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1866) "Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Beach nearby, sun-loungers, beach towels](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/aaa820d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/520df554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants North Beach 10/10 Exceptional (30) "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. £387 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.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) ![Presidential Single Room, 1 King Bed, Bathtub, Harbour View | Frette Italian sheets, premium bedding, down duvets, memory-foam beds](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/15680a18.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/74000000/73380000/73371800/73371779/42213387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (28) "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) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/ba6b073a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 Exceptional (71) "The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent W. £236 includes taxes & fees 3 Nov - 4 Nov [](https://www.expedia.co.uk/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/1c22c0d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/bbbfca07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/77b3036c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/126a7308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home in Downtown Annapolis Historic District £536 includes taxes & fees 29 Oct - 30 Oct [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.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) ![Superior Double Room, City View | In-room safe, blackout curtains, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/eaea568e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel Historic District 10/10 Exceptional (2) "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 29 Oct - 30 Oct [](https://www.expedia.co.uk/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![3 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/1b8e0fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/c86eb9a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/3c0a3b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/6e7508c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ★ Midcentury Modern Getaway ★ Prime Location ★ Historic District 10/10 Exceptional (35) "This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) shannon r. £425 includes taxes & fees 4 Nov - 5 Nov [](https://www.expedia.co.uk/Annapolis-Hotels-Midcentury-Modern-Getaway-Prime-Location.h48624274.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/3d98a748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/876912bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/a6db755d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/174999ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Downtown Annapolis Condo With Free Parking Historic District 10/10 Exceptional (31) "The apartment is exactly what we expected and was a great place to stay! Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Megan U. £284 includes taxes & fees 17 Nov - 18 Nov [](https://www.expedia.co.uk/Annapolis-Hotels-Downtown-Annapolis-Condo-W-Free-Parking-Coffee.h69666468.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/001f8463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w904h683x60y0-dec863ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/598d88e9_edited_b6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Cent. Charm in Historic Downtown Annapolis Historic District 9.0/10 Wonderful (12) "Property description is accurate, host is quickly responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradford R. £263 includes taxes & fees 29 Oct - 30 Oct [](https://www.expedia.co.uk/Annapolis-Hotels-Charming-18th-Cent-Home-In-Historic-Downtown-Annapolis.h92564827.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=2025-11-11&endDate=2025-11-12®ionId=553248635077608788&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Kent Island Hotel Reviews ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "Breakfast was very good,has plenty of varieties to choose from. Parking lot has plenty of lighting making it feel safe. It was a quiet even backed up to a high way. Staff very friendly and helpful." [](https://expedia.co.uk/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Lovely room" [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Country Inn & Suites by Radisson, Annapolis, MD](//images.trvl-media.com/lodging/1000000/150000/140400/140359/d2b7f950_y.jpg) ### Country Inn & Suites by Radisson, Annapolis, MD 10/10 Excellent "The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it." [](https://expedia.co.uk/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "I am a healthcare traveler and I work night shift. Unlike most people who go to a hotel, i need a bed for day time sleep and an esrly check in. The front desk agents accommodated my early check in and gave me a clean room at 9am. I went to sleep right away. No noise, no dirty bathroom. Plus the buffet was a huge plus. I booked all my other stays here. This will be home for the next couple of weeks. Everyone had a welcoming smile. " [](https://expedia.co.uk/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Room was very clean." [](https://expedia.co.uk/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Hilton Garden Inn Annapolis Downtown](//images.trvl-media.com/lodging/1000000/900000/892300/892213/4fdee6d5_y.jpg) ### Hilton Garden Inn Annapolis Downtown 10/10 Excellent "Clean room, great staff, great breakfast " [](https://expedia.co.uk/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were exceedingly helpful and friendly. Parking was close and easy." [](https://expedia.co.uk/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![The Westin Annapolis](//images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "All was good " [](https://expedia.co.uk/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Wonderfully. We were pleasantly surprised at the hotel. Very nice. Well decorated. Convenient and walkable location. 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