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 [Feb 6 - Feb 7](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-02-06&endDate=2026-02-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-02-07&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake historic hotels ![Interior](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/90-2c7becfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/90-3c6fbccd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/90-7b6f370e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/615c5936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Water Front Delight on the Bay [](https://www.expedia.ca/Norfolk-Hotels-Water-Front-Delight-On-The-Bay.h52073959.Hotel-Information) Willoughby Spit 7.8/10 Good (25 reviews) "Everything was very nice really enjoyed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah B. CA $136 CA $488 total includes taxes & fees Feb 28 - Mar 1 [](https://www.expedia.ca/Norfolk-Hotels-Water-Front-Delight-On-The-Bay.h52073959.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/395bd0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/f8c0be75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/4912ecf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/55953ee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Smithfield Inn [](https://www.expedia.ca/Smithfield-Hotels-Smithfield-Inn.h22624734.Hotel-Information) Smithfield 8.8/10 Excellent (108 reviews) "I enjoyed the friendly hospitality " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neslihan Christobel CA $286 CA $320 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Smithfield-Hotels-Smithfield-Inn.h22624734.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69540000/69537000/69536918/6aabd7ae.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) ### 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 9.0/10 Wonderful (69 reviews) "Amazing little cottage right on the water. Would love to stay again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ROBYN B. CA $177 CA $360 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Norfolk-Hotels-Rustic-Ocean-View-Beach-House-BEST-Location-In-Ocean-View-2-Bed1-Bath-House.h69536918.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/980000/978200/978102/044ccb86.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 (1,003 reviews) "Good staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $92 CA $131 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Virginia-Beach-Hotels-Sandcastle-Resort-On-The-Beach.h978102.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) ![Dining](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/aaec7fd2.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) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21670000/21667100/21667042/1a33ec0f.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 $340 CA $982 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Norfolk-Hotels-Old-Beach-House-Made-New-For-Large-Accommodations.h21667042.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/125000000/124350000/124345800/124345722/89c68553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/125000000/124350000/124345800/124345722/44b9a899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124350000/124345800/124345722/c38bc954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/125000000/124350000/124345800/124345722/44a00284.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Downtown Apartment w/patio. [](https://www.expedia.ca/Norfolk-Hotels-Cozy-1-Bedroom-Apartment-With-AC-In-Serene-Norfolk.h124345722.Hotel-Information) Downtown Norfolk CA $165 CA $302 total includes taxes & fees Mar 6 - Mar 7 [](https://www.expedia.ca/Norfolk-Hotels-Cozy-1-Bedroom-Apartment-With-AC-In-Serene-Norfolk.h124345722.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/10000000/9340000/9331000/9330915/347113bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/10000000/9340000/9331000/9330915/053df2e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking (Newly Renovated)](https://images.trvl-media.com/lodging/10000000/9340000/9331000/9330915/11484397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9340000/9331000/9330915/8b55a177.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### White Marlin Inn [](https://www.expedia.ca/Virginia-Beach-Hotels-White-Marlin-Inn.h9330915.Hotel-Information) Northeast Virginia Beach 5.2/10 (1,000 reviews) "👍" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $57 CA $75 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Virginia-Beach-Hotels-White-Marlin-Inn.h9330915.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=2026-02-20&endDate=2026-02-21®ionId=6612&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Hotel Reviews ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/c80e2694_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront) 10/10 Excellent "Great room! Clean and tidy. Amazing ocean view. Breakfast was great, offered eggs, bacon, muffins, waffles, bagels, cereals, and much more. Definitely stay here again! " [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_y.jpg) ### Wingate by Wyndham Chesapeake 10/10 Excellent "Great customer service" [](https://expedia.ca/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Embassy Suites by Hilton Hampton Convention Center](https://images.trvl-media.com/lodging/2000000/1180000/1172300/1172219/5d92420f_y.jpg) ### Embassy Suites by Hilton Hampton Convention Center 10/10 Excellent "The room was clean. In general the facility is well maintained. All the staff was very helpful and warm. The standout is the manager CeeCee. I am not sure if the correct spelling of her name. But, she is everything that hospitality stands for. I plan on calling corporate to sing her praises! Embassy Suites is the product we usually stay at in Ft. Lauderdale for a cruise. It seems like the culture is chain wide. I absolutely enjoyed staying here. We will be back!" [](https://expedia.ca/Newport-News-Hotels-Embassy-Suites-By-Hilton-Hampton-Convention-Center.h1172219.Hotel-Information) ![Comfort Inn Newport News - Hampton I-64](https://images.trvl-media.com/lodging/1000000/20000/10200/10111/01f0ccae_y.jpg) ### Comfort Inn Newport News - Hampton I-64 10/10 Excellent "Great" [](https://expedia.ca/Newport-News-Hotels-Comfort-Inn-Newport-News-Hampton-I-64.h10111.Hotel-Information) ![Wyndham Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/1000000/10000/8200/8175/41603c72_y.jpg) ### Wyndham Virginia Beach Oceanfront 10/10 Excellent "Yes" [](https://expedia.ca/Virginia-Beach-Hotels-Wyndham-Virginia-Beach-Oceanfront.h8175.Hotel-Information) ![Fairfield Inn and Suites By Marriott Chesapeake](https://images.trvl-media.com/lodging/1000000/20000/16100/16036/234312b3_y.jpg) ### Fairfield Inn and Suites By Marriott Chesapeake 10/10 Excellent "Friendly staff" [](https://expedia.ca/Chesapeake-Hotels-Fairfield-Inn-And-Suites-By-Marriott-Chesapeake.h16036.Hotel-Information) ![Hilton Vacation Club Ocean Beach Club Virginia Beach](https://images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/b6b50f9a_y.jpg) ### Hilton Vacation Club Ocean Beach Club Virginia Beach 10/10 Excellent "Last week I stayed at the Hilton Ocean Beach Club Hotel. It's not my first time staying at this property and it won't be my last. I chose to come during winter so as not to compete with too many other visitors for relaxation, peace and quiet. I usually come when the weather is warm. I was checked in by Marquita who was a delight from beginning to end with my check-in process. I had an ocean view studio room with a kitchenette in it which made it nice to put simple things together to eat when I didn't want to venture out too far. These rooms have floor to ceiling windows which makes watching the ocean intoxicating. I saw a school of dolphins practically every morning which made my eyes dance. By my second night I was having comfort issues with the bed and rose my concern at the front desk. Aishadia overheard my concern and stepped in to take over from the person I initially began talking with. Aishadia gave me the energy that my personal comfort and satisfaction was her #1 goal....and guess what, she SCORED! I was smoothly and easily moved to another room that was more suited and I was ever so grateful. The day I was checking out my room phone rang. It was Ms. Luvinia. She had called to check and see how my stay had been. STELLAR!, I told her. We talked about the similarity and history of our first names. We're both named after our Great-Grandmother's. How special is that. :-) Thanks to the team for making my stay so easy, comfortable and relaxing." [](https://expedia.ca/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![Hilton Virginia Beach Oceanfront](https://images.trvl-media.com/lodging/2000000/1160000/1156000/1155964/982abe80_y.jpg) ### Hilton Virginia Beach Oceanfront 10/10 Excellent "Great stay, great staff" [](https://expedia.ca/Virginia-Beach-Hotels-Hilton-Virginia-Beach-Oceanfront.h1155964.Hotel-Information) ![SureStay Hotel by Best Western Virginia Beach Royal Clipper](https://images.trvl-media.com/lodging/1000000/450000/441300/441218/2644c33a_y.jpg) ### SureStay Hotel by Best Western Virginia Beach Royal Clipper 10/10 Excellent "Mr. Bryan was very helpful and jolly. The room was very clean." [](https://expedia.ca/Virginia-Beach-Hotels-SureStay-Hotel-By-Best-Western-Virginia-Beach-Royal-Clipper.h441218.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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