Title: Book the Best HISTORIC Hotels in Chesapeake in 2026 | Expedia.ca [Chesapeake Travel Guide](https://expedia.ca/Chesapeake.dx6612)[Hotels in Chesapeake](https://expedia.ca/Chesapeake-Hotels.d6612.Travel-Guide-Hotels)[Vacation Rentals in Chesapeake](https://expedia.ca/Chesapeake-Vacation-Rentals.d6612.Travel-Guide-VacationRentals)[Flights to Chesapeake](https://expedia.ca/Cheap-Flights-To-Chesapeake.d6612.Travel-Guide-Flights)[Chesapeake Car Rentals](https://expedia.ca/Car-Rentals-In-Chesapeake.d6612.Car-Rental-Guide)[Chesapeake Vacation Packages](https://expedia.ca/Chesapeake.d6612.Destination-Travel-Guides) ![Hidden Gems. #trovember #chesapeake #virginia #november #fall #golden #hiddengems](https://images.trvl-media.com/place/6612/dba409e5-c541-4029-b3b6-3ea7a408a4c8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Sarah Chiricosta ![](https://images.trvl-media.com/place/6612/dba409e5-c541-4029-b3b6-3ea7a408a4c8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Chesapeake Historic Hotels Tonight [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-03-24&endDate=2026-03-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 25 - Mar 26](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-03-25&endDate=2026-03-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake historic hotels ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/b918f4ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/53759327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/695576fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/da4b144a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norfolk Beach Cottage Rental [](https://www.expedia.ca/Norfolk-Virginia-Beach-Hotels-Norfolk-Beach-Cottage-Rental.h33556489.Hotel-Information) East Ocean View 9.0/10 Wonderful (280 reviews) "Great location. Very close to the beach and a park. Great place for families. Large dining table worked great for us for Thanksgiving. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cody H. CA $228 CA $554 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Norfolk-Virginia-Beach-Hotels-Norfolk-Beach-Cottage-Rental.h33556489.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/b693ca3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/a9f07483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/317971bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/25f8f073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House [](https://www.expedia.ca/Norfolk-Hotels-Rustic-Ocean-View-Beach-House-BEST-Location-In-Ocean-View-2-Bed1-Bath-House.h69536918.Hotel-Information) Willoughby Spit 8.8/10 Excellent (70 reviews) "We love this little quiet beach house " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annie N. CA $177 CA $359 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Norfolk-Hotels-Rustic-Ocean-View-Beach-House-BEST-Location-In-Ocean-View-2-Bed1-Bath-House.h69536918.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/9dc52334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, books](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/4ff18bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/270-9c96451f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/aaec7fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Beach House Made New for Large Accommodations [](https://www.expedia.ca/Norfolk-Hotels-Old-Beach-House-Made-New-For-Large-Accommodations.h21667042.Hotel-Information) Norfolk 9.2/10 Wonderful (15 reviews) "Spacious and very clean! Perfect for a big family gathering." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer S. CA $424 CA $1,093 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Norfolk-Hotels-Old-Beach-House-Made-New-For-Large-Accommodations.h21667042.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/980000/978200/978102/1f12daa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/980000/978200/978102/40330202.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/980000/978200/978102/3229a177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/978200/978102/e9bde5c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sandcastle Resort On The Beach [](https://www.expedia.ca/Virginia-Beach-Hotels-Sandcastle-Resort-On-The-Beach.h978102.Hotel-Information) Northeast Virginia Beach 7.6/10 Good (1,002 reviews) "Clean rooms, staff was nice, and I had a balcony where I could see the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Renee CA $99 CA $138 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Virginia-Beach-Hotels-Sandcastle-Resort-On-The-Beach.h978102.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=2026-04-07&endDate=2026-04-08®ionId=6612&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Hotel Reviews ![Hilton Vacation Club Ocean Beach Club Virginia Beach](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/44e2a487_y.jpg) ### Hilton Vacation Club Ocean Beach Club Virginia Beach 8/10 Good "The staff was very friendly upon arrival. With it being marathon weekend, they were super helpful providing details on road closures. The room was clean and spacious. My only complaint was some mold on the bottom of the shower curtain. Aside from that, everything else was clean upon arrival. The hotel is conveniently located along the boardwalk with some great restaurants in walking distance." [](https://expedia.ca/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![Hilton Vacation Club Oceanaire Virginia Beach](https://images.trvl-media.com/lodging/6000000/5200000/5190800/5190701/35a4a7e3_y.jpg) ### Hilton Vacation Club Oceanaire Virginia Beach 6/10 Okay "Paying for a suite plus the room size was amazing but being the literally floor over the sun deck really took away from the view and overall ambiance of the stay." [](https://expedia.ca/Virginia-Beach-Hotels-Oceanaire-By-Diamond-Resorts.h5190701.Hotel-Information) ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/be66f1fd_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 10/10 Excellent "The facility and our room was very clean. Check-in and checkout was quick and easy with very friendly staff. My family enjoyed the breakfast also." [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Hilton Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/2000000/1160000/1156000/1155964/3b10b192_y.jpg) ### Hilton Virginia Beach Oceanfront 10/10 Excellent "Great location, nice place." [](https://expedia.ca/Virginia-Beach-Hotels-Hilton-Virginia-Beach-Oceanfront.h1155964.Hotel-Information) ![Coastal Hotel and Suites Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/10000/9977/77100d53_y.jpg) ### Coastal Hotel and Suites Virginia Beach Oceanfront 8/10 Good "The breakfast was great and extremely friendly staff. " [](https://expedia.ca/Virginia-Beach-Hotels-Coastal-Hotel-And-Suites-Virginia-Beach-Oceanfront.h9977.Hotel-Information) ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/0d94729b_y.jpg) ### Wingate by Wyndham Chesapeake 10/10 Excellent "Gym was ok " [](https://expedia.ca/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/038be8fc_y.jpg) ### Comfort Suites Chesapeake - Norfolk 8/10 Good "The lobby was beautifully updated BUT the elevator was not working which make carrying lounge difficult " [](https://expedia.ca/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information) ![Moxy Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/5000000/4670000/4665200/4665123/8673ad8e_y.jpg) ### Moxy Virginia Beach Oceanfront 10/10 Excellent "Tge pool was gross and not functional. Beach view was amazing. Balcony room was perfect! The adult slide in the lobby was a hit for my kids. " [](https://expedia.ca/Norfolk-Virginia-Beach-Hotels-Baymont-By-Wyndham-Virginia-Beach-Oceanfront.h4665123.Hotel-Information) ![Holiday Inn Va Beach-Oceanside (21st St) by IHG](https://images.trvl-media.com/lodging/1000000/10000/4900/4857/c65c289f_y.jpg) ### Holiday Inn Va Beach-Oceanside (21st St) by IHG 8/10 Good "Room was clean and comfortable Was booked into a handicap accessible room (not requested) which had no chair or sofa in the room. Was informed that was standard which I found to be unusual. Staff was friendly most especially the valet who made great restaurant recommendations. Thanks " [](https://expedia.ca/Virginia-Beach-Hotels-Holiday-Inn-Oceanside-VA-Beach.h4857.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Chesapeake? ### How many historical hotels will I find in Chesapeake? ### What are the must-see historical places and other sights to visit in Chesapeake? ### What is a historic hotel like in Chesapeake? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Chesapeake have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Hotels near Chesapeake Conference Center ](https://www.expedia.ca/Chesapeake-Conference-Center-Hotels.0-l6083013-0.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Deep Creek South ](https://www.expedia.ca/Deep-Creek-South-Chesapeake-Hotels-Adults-Only-Resorts.0-n553248635976473910-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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