Title: Book the Best HISTORIC Hotels in Eastport in 2026 | 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) ![Aerial view of colorful sailboat moorings and docks on Spa Creek, in historic downtown Annapolis Maryland on a fall day](https://images.trvl-media.com/place/553248635976473127/b398174a-daca-40f4-a397-3fb8131cb169.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Eastport, MD from CA $304 - ![](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 [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-12-01&endDate=2025-12-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 2 - Dec 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-12-02&endDate=2025-12-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473127&startDate=2025-12-12&endDate=2025-12-14&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) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.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 (1912) "Excellent hotel Really nice staff Love the valet guys " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ben [](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) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.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) ![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 (81) "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 CA $267 CA $304 total includes taxes & fees Dec 4 - Dec 5 [](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) ![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) ![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) ### 134 Prince - Luxury Boutique Hotel Annapolis 9.8/10 Exceptional (30) "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.ca/Annapolis-Hotels-134-Prince-Luxury-Boutique-Hotel.h73371779.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) ![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) ### Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants 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. CA $137 CA $568 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/North-Beach-Hotels-Huge-Beach-Bungalow-WYard.h83966408.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) ![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) ![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 (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 CA $445 CA $508 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.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) ![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) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 Exceptional (72) "Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheldon E. CA $169 CA $433 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/a05c57e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117590000/117588800/117588789/w1359h906x3y0-2211d6c9.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 (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. CA $189 CA $991 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-1-Block-From-Gate-1-At-USNA.h117588789.Hotel-Information) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/1b8e0fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/49000000/48630000/48624300/48624274/ed81b1a0.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) ![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) ### ★ 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. CA $245 CA $775 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Annapolis-Hotels-Midcentury-Modern-Getaway-Prime-Location.h48624274.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) ![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) ### Historic Row Home in Downtown Annapolis Historic District CA $182 CA $966 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Row-Home-In-Downtown-Annapolis.h118891568.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w950h680x38y3-96439ab6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w816h682x104y0-a072a320.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w905h683x60y0-0737769d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/93000000/92570000/92565900/92565863/w707h678x157y5-ccae639e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Cozy Cottage in Historic Downtown Historic District 9.6/10 Exceptional (16) "We had a very lovely stay . This is an excellent location . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly B. CA $629 CA $1,047 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Annapolis-Hotels-Secluded-Cozy-Cottage-In-Historic-Downtown.h92565863.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=2025-12-16&endDate=2025-12-17®ionId=553248635976473127&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Eastport Hotel Reviews ![Sonesta ES Suites Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3000/2982/e773fcbe_y.jpg) ### Sonesta ES Suites Annapolis 10/10 Excellent "Everything was great especially the staff" [](https://expedia.ca/Annapolis-Hotels-Sonesta-ES-Suites-Annapolis.h2982.Hotel-Information) ![Holiday Inn Baltimore BWI Airport by IHG](https://images.trvl-media.com/lodging/1000000/80000/77900/77834/77790c2d_y.jpg) ### Holiday Inn Baltimore BWI Airport by IHG 10/10 Excellent "Overnight stay. The shuttle driver was an awesome guy. " [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Baltimore-BWI-Airport.h77834.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 "Evening bar staff was exceptional, as was the crew at the check-in desk. Excellent recommendations for places to eat. This hotel is within walking distance of everything we wanted to see and do. So much history here, cool stores, venues, and not far from the bay." [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis-Downtown.h892213.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 hotel Really nice staff Love the valet guys " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![The Hotel at Arundel Preserve](https://images.trvl-media.com/lodging/5000000/4550000/4542400/4542302/bd8bd966_y.jpg) ### The Hotel at Arundel Preserve 10/10 Excellent "The hotel was very peaceful. I definitely would come back." [](https://expedia.ca/Baltimore-Hotels-The-Hotel-At-Arundel-Preserve.h4542302.Hotel-Information) ![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 "Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!" [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Country Inn & Suites by Radisson, BWI Airport (Baltimore), MD](https://images.trvl-media.com/lodging/2000000/1200000/1194300/1194292/784b5f17_y.jpg) ### Country Inn & Suites by Radisson, BWI Airport (Baltimore), MD 10/10 Excellent "Good location. Quiet and clean room. Comfortable bed. Friendly, helpful staff, especially shuttle drivers. " [](https://expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h1194292.Hotel-Information) ![Hilton Baltimore BWI Airport](https://images.trvl-media.com/lodging/2000000/1520000/1518600/1518537/78c7fba5_y.jpg) ### Hilton Baltimore BWI Airport 10/10 Excellent "All of the above" [](https://expedia.ca/Baltimore-Hotels-Hilton-Baltimore-BWI-Airport.h1518537.Hotel-Information) ![Aloft BWI Baltimore Washington International Airport](https://images.trvl-media.com/lodging/3000000/2810000/2804100/2804098/12d1a93d_y.jpg) ### Aloft BWI Baltimore Washington International Airport 10/10 Excellent "Yes" [](https://expedia.ca/Baltimore-Hotels-Aloft-BWI-Baltimore-Washington-International-Airport.h2804098.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 81 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 Annapolis City Dock 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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