Title: Book the Best HISTORIC Hotels in Eastport in 2025 | Expedia.ca [Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Eastport Car Rentals](https://expedia.ca/Car-Rentals-In-Eastport.d553248635976473127.Car-Rental-Guide)[Eastport Vacations](https://expedia.ca/Eastport.d553248635976473127.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Eastport, MD from CA $214 ![](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 Eastport Historic Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Eastport Historic Hotels ![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 (1848) "The hotel was absolutely clean and close to the shops and restaurants. " 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) ![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) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.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/w1857h2500x0y0-ac5cefb5.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!" CA $329 CA $375 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/116000000/115970000/115964600/115964505/a8bf1b01.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) ![Superior Double Room, City View](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." CA $515 CA $588 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.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) ![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) ![Interior](https://images.trvl-media.com/lodging/84000000/83970000/83966500/83966408/d4e67bdb.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. " CA $250 CA $701 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/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) ![Meeting facility](https://images.trvl-media.com/lodging/74000000/73380000/73371800/73371779/42213387.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) ![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 (26) "Very friendly staff!" CA $287 CA $328 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.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) ![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) ![Interior](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h908x3y2-e4e5546a.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) ### Historic Row Home 1 Block from Gate 1 at USNA! Historic District 10/10 Exceptional (2) "Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! " CA $217 CA $1,030 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-1-Block-From-Gate-1-At-USNA.h117588789.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) ![Interior](https://images.trvl-media.com/lodging/70000000/69670000/69666500/69666468/174999ba.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) ### 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. " CA $209 CA $519 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Annapolis-Hotels-Downtown-Annapolis-Condo-W-Free-Parking-Coffee.h69666468.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" CA $183 CA $458 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) ![Pool](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/be9b544d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/90fa709b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/42cc6993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33510000/33506400/33506340/4c819a0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK Churchton 9.8/10 Exceptional (82) "The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again." CA $391 CA $643 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Churchton-Hotels-Watrfnt-Cottage-ChesapeakeParadise-KayaksDogs-OK.h33506340.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) ![Outdoor dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/126a7308.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) ![Dining](https://images.trvl-media.com/lodging/119000000/118900000/118891600/118891568/77b3036c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Row Home in Downtown Annapolis Historic District CA $206 CA $1,006 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=553248635976473127&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Eastport Hotel Reviews ![Sonesta ES Suites Annapolis](//images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Our night at your hotel was just fine! Room was clean. Supply toiletries, towels for the bath and kitchen were as expected, neat and plentiful. There was a creak in the bathroom door, but that is a nitpick. Coffee maker was easy to operate. Breakfast was as expected, with some delay when coffee carafe and food service trays were empty. I would go back." [](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 "The hotel was absolutely clean and close to the shops and restaurants. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Comfort Inn Conference Center](//images.trvl-media.com/lodging/1000000/20000/17300/17201/925f7921_y.jpg) ### Comfort Inn Conference Center 10/10 Excellent " Fine " [](https://expedia.ca/Annapolis-Hotels-Comfort-Inn-Conference-Center.h17201.Hotel-Information) ![Towneplace Suites by Marriott Arundel Mills](//images.trvl-media.com/lodging/3000000/2220000/2217700/2217669/ad99265e_y.jpg) ### Towneplace Suites by Marriott Arundel Mills 10/10 Excellent "Nice place. Great location. Nice staff." [](https://expedia.ca/Baltimore-Hotels-Towneplace-Suites-By-Marriott-Arundel-Mills.h2217669.Hotel-Information) ![Aloft BWI Baltimore Washington International Airport](//images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/12d1a93d_y.jpg) ### Aloft BWI Baltimore Washington International Airport 10/10 Excellent "Easily accessible and the room was great. " [](https://expedia.ca/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.Hotel-Information) ![The Hotel at Arundel Preserve](//images.trvl-media.com/lodging/5000000/4550000/4542400/4542302/bd8bd966_y.jpg) ### The Hotel at Arundel Preserve 10/10 Excellent "clean room, friendly check-in, great restaurant on premise" [](https://expedia.ca/Baltimore-Hotels-The-Hotel-At-Arundel-Preserve.h4542302.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 "Bed linens were very disappointing. Pillows, sheets and blanket were flimsy and cheap. " [](https://expedia.ca/Annapolis-Hotels-Country-Inn-Suites-By-Radisson.h140359.Hotel-Information) ![Holiday Inn Express Baltimore-BWI Airport West by IHG](//images.trvl-media.com/lodging/1000000/10000/2400/2353/b44bf96e_y.jpg) ### Holiday Inn Express Baltimore-BWI Airport West by IHG 10/10 Excellent "Great stay!" [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-Baltimore-BWI-Airport-West.h2353.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 " Very clean and fresh room The TV screen already had my name on it !" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ## Frequently asked questions ### What can a history enthusiast expect from a trip to Eastport? > Significant historical sites in Eastport are likely at the top of your sightseeing list. And while you're visiting the area, why not also discover all of the sights in the area? ### How many historical hotels are located in Eastport? > Eastport is home to 62 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the must-see historical sites and other places to visit in Eastport? > Favorite places to visit include Annapolis Maritime Museum, Annapolis Harbor, and Spa Creek. You'll also find Annapolis Landing Marina and Ego Alley in the area. ### What is a historic hotel like in Eastport? > A historic hotel gives guests the opportunity to stay in a building that has been recognized with a national historic designation. Historic hotels throughout the world can take the form of palaces, castles, stately homes or even lodges, pubs, or skyscrapers. These types of hotels in Eastport often retain original elements such as period features or traditional architecture within the guestrooms or public spaces. ### What is the difference between a historic hotel and a heritage hotel? > These are quite similar. "Historic hotel" is a term often used in the U.S., whereas "heritage hotel" is common in Asia and Europe. Historic hotels tend to put more importance on the building and architecture itself. Mainly heritage hotels draw meaning from the cultural value and how it shaped the community. ### Do historic hotels in Eastport have modern facilities? > Yes. Every effort is made to preserve historic facades and treasured traditions, but hotel interiors are fitted with modern conveniences and safety features. Guests can expect the usual amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. In Eastport, booking a historic hotel doesn't mean you're picking a place that's uncomfortable for guests or simply rundown. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Annapolis](https://www.expedia.ca/4Star-Annapolis-Hotels.s40-0-d6034082.Travel-Guide-Filter-Hotels) - [Farmstay in Annapolis](https://www.expedia.ca/Annapolis-Agritourism.d6034082-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Annapolis](https://www.expedia.ca/Annapolis-Apart-Hotels.d6034082-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Annapolis](https://www.expedia.ca/Annapolis-Bed-And-Breakfast.d6034082-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Capsule Hotels in Annapolis](https://www.expedia.ca/Annapolis-Capsule-Hotels.d6034082-aaCapsuleHotels.Travel-Guide-Accommodation) - [Castles in Annapolis](https://www.expedia.ca/Annapolis-Castles.d6034082-aaCastles.Travel-Guide-Accommodation) - [Chalets in Annapolis](https://www.expedia.ca/Annapolis-Chalets.d6034082-aaChalets.Travel-Guide-Accommodation) - 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