Title: Book the Best HISTORIC Hotels in Kent Island in 2025 | 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 # Find Historic Hotels in Kent Island, MD ![](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 Historic Hotels Tonight [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-26&endDate=2025-10-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635077608788&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/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 ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed (Safari Suite (at Tidewater House))](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.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) ### The Tidewater Inn Easton 8.8/10 Excellent (834) "Great hotel! Stayed there multiple times." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $251 CA $276 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) ![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) ![Waterfront Suite | Living area](https://images.trvl-media.com/lodging/103000000/102620000/102610200/102610148/0787536d.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) ### Wylder Tilghman Island Tilghman 8.8/10 Excellent (86) "Very relaxing stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $227 CA $311 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/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) ![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) ![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 (1853) "The hotel was absolutely clean and close to the shops and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trudy CA $145 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/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) ![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 crib](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/67700a38.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) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants North Beach 10/10 Exceptional (30) "Absolutely beautiful and spacious home perfectly located in North Beach. Very peaceful area and close to the beach, restaurants and shopping. We really enjoyed our stay and hope to visit again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vicki K. CA $228 CA $686 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/6c83d519.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) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (79) "Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $256 CA $292 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/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) ![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) ![Presidential Single Room, 1 King Bed, Bathtub, Harbour View](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/15680a18.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 CA $275 CA $314 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.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) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/7d0396b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home in Downtown Annapolis Historic District CA $175 CA $965 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.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) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/5acb80c3.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) ![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. CA $164 CA $432 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/d953bc28.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. CA $208 CA $518 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Downtown-Annapolis-Condo-W-Free-Parking-Coffee.h69666468.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) ![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) ### 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 CA $451 CA $515 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.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.ca/Hotel-Search?startDate=2025-11-08&endDate=2025-11-09®ionId=553248635077608788&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Kent Island Hotel Reviews ![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 "First time staying here, Hotel staff were amazing, hotel was so welcoming and clean, our room was perfect. Loved the jetted tub, perfect for 2, and the fireplace set the tone for a great stay. Shower was huge, and so was our room. Breakfast was hot and delicious. Made for a great couple's getaway. " [](https://expedia.ca/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 "Staff was amazing..Staff keep all of the area clean Staff is amazing.." [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.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.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.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 and comfortable. " [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.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 "Loved everything. Perfect location right on the main drag " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.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 "Nice rooms. " [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.Hotel-Information) ![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent "Friendly staff and comfortable rooms. We love staying here when we visit the area as a family." [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![Courtyard by Marriott Annapolis](//images.trvl-media.com/lodging/1000000/20000/11100/11049/122348e3_y.jpg) ### Courtyard by Marriott Annapolis 10/10 Excellent "It was just what I needed. Seems safe. It was clean and quiet." 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