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 # Find Historic Hotels in Chesapeake, VA from CA $112 - ![](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 [Dec 16 - Dec 17](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 17 - Dec 18](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-12-17&endDate=2025-12-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6612&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chesapeake historic hotels ![On the beach](https://images.trvl-media.com/lodging/60000000/59960000/59951000/59950921/f4fb49eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59960000/59951000/59950921/2abf5420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/60000000/59960000/59951000/59950921/44493e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59960000/59951000/59950921/2bf4d03a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Side Studio #2 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV [](https://www.expedia.ca/Norfolk-Hotels-Beach-Side-Studio-2-Pet-Friendly.h59950921.Hotel-Information) Cottage Line 8.4/10 Very good (16) "Very comfy vibe. Had a great time staying here!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paola G. CA $54 CA $207 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Norfolk-Hotels-Beach-Side-Studio-2-Pet-Friendly.h59950921.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/59000000/58950000/58945100/58945030/f79d53a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/59000000/58950000/58945100/58945030/ad66a302.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/59000000/58950000/58945100/58945030/685c091a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/59000000/58950000/58945100/58945030/cf6b8102.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Side Studio #1 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV [](https://www.expedia.ca/Beach-Side-Studio-1-Pet-Friendly.h58945030.Hotel-Information) Norfolk 7.6/10 Good (23) "Easy and convenient location! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erica J. CA $54 CA $205 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Beach-Side-Studio-1-Pet-Friendly.h58945030.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/23000000/22630000/22624800/22624734/8b01c36b.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) ![Miscellaneous](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/f8c0be75.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 9.0/10 Wonderful (102) "Friendly staff Charming bed & breakfast nearby shops/dining convenient parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Woody CA $219 CA $245 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Smithfield-Hotels-Smithfield-Inn.h22624734.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/db23ac04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/f571f46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/a74fe604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/0bfd1a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Virginia Beach At The Beach [](https://www.expedia.ca/Virginia-Beach-Hotels-Days-Inn-By-Wyndham-Virginia-Beach-At-The-Beach.h43282.Hotel-Information) Northeast Virginia Beach 7.8/10 Good (1001) " No complaints, it was cleanand staff was friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joy CA $95 CA $112 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Virginia-Beach-Hotels-Days-Inn-By-Wyndham-Virginia-Beach-At-The-Beach.h43282.Hotel-Information) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/159a3612.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 (278) "Held my daughter’s sweet 16 slumber party here the girls loved it awesome time and the host family is awesome!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merinda F. CA $229 CA $551 total includes taxes & fees Dec 18 - Dec 19 [](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) ![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) ### 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) "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 $178 CA $359 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Norfolk-Hotels-Rustic-Ocean-View-Beach-House-BEST-Location-In-Ocean-View-2-Bed1-Bath-House.h69536918.Hotel-Information) ![Suite, 2 Double Beds (Partial Ocean View, Smoke Free)](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/a423f2ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds (Partial Ocean View, Smoke Free)](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/16a829ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/a9bd9b8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/4341594f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof PLUS+ & Suites Virginia Beach – Seaside [](https://www.expedia.ca/Virginia-Beach-Hotels-Rodeway-Inn-By-The-Beach.h197069.Hotel-Information) Northeast Virginia Beach 8.4/10 Very good (1034) "Great stay.. Quiet & clean. Will stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kashmere [](https://www.expedia.ca/Virginia-Beach-Hotels-Rodeway-Inn-By-The-Beach.h197069.Hotel-Information) ![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) ![Smart TV](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/615c5936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/53000000/52080000/52074000/52073959/90-2c7becfa.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) ### 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) "Everything was very nice really enjoyed " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah B. CA $219 CA $590 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Norfolk-Hotels-Water-Front-Delight-On-The-Bay.h52073959.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/49e51f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking, Balcony | Lake view](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/1b20f4a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fishing](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/45c350b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Multiple Beds, Non Smoking, Pool View | Living area](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/b3b397bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seashire Inn & Suites [](https://www.expedia.ca/Virginia-Beach-Hotels-Seashire-Inn-Suites.h2758929.Hotel-Information) Northeast Virginia Beach 7.4/10 Good (378) "Great staff good hotel rooms close to beach and 711 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terri [](https://www.expedia.ca/Virginia-Beach-Hotels-Seashire-Inn-Suites.h2758929.Hotel-Information) ![Lunch and dinner served, beach views ](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/a8dfbecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/ebea36ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/46489907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Partial Oceanfront, 1 King Bed, 1 Sofa Bed, Accessible, Roll-In Shower](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/w3837h2560x3y0-6756040e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Virginia Beach-Oceanfront South [](https://www.expedia.ca/Virginia-Beach-Hotels-Hampton-Inn-Virginia-Beach-Oceanfront-South.h2820807.Hotel-Information) Northeast Virginia Beach 8.8/10 Excellent (1052) "Clean room, great service and a wonderful stay.😊" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carroll CA $148 CA $173 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Virginia-Beach-Hotels-Hampton-Inn-Virginia-Beach-Oceanfront-South.h2820807.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=2025-12-31&endDate=2026-01-01®ionId=6612&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Hotel Reviews ![Comfort Suites Chesapeake - Norfolk](https://images.trvl-media.com/lodging/1000000/10000/6600/6570/74e17a93_y.jpg) ### Comfort Suites Chesapeake - Norfolk 10/10 Excellent "Everything was the way it should be. Well done." [](https://expedia.ca/Chesapeake-Hotels-Comfort-Suites-Chesapeake-Norfolk.h6570.Hotel-Information) ![Aloft Chesapeake](https://images.trvl-media.com/lodging/3000000/2180000/2178600/2178508/40b8c7ba_y.jpg) ### Aloft Chesapeake 10/10 Excellent "I didn’t wake up early enough for breakfast but next time I will. I love this place for my solo self care trips. " [](https://expedia.ca/Chesapeake-Hotels-Aloft-Chesapeake.h2178508.Hotel-Information) ![Holiday Inn Express Chesapeake - Norfolk by IHG](https://images.trvl-media.com/lodging/1000000/10000/4300/4253/a34808e1_y.jpg) ### Holiday Inn Express Chesapeake - Norfolk by IHG 10/10 Excellent "Clean, amenities and spacious " [](https://expedia.ca/Chesapeake-Hotels-Holiday-Inn-Express-Chesapeake-Norfolk.h4253.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 "Everything was so nice" [](https://expedia.ca/Newport-News-Hotels-Embassy-Suites-By-Hilton-Hampton-Convention-Center.h1172219.Hotel-Information) ![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 "The room was clean and beautiful. The breakfast buffet was delicious. The entire staff was friendly and accommodating. " [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Norfolk Waterside Marriott](https://images.trvl-media.com/lodging/1000000/20000/15000/14905/3501760d_y.jpg) ### Norfolk Waterside Marriott 10/10 Excellent "Yes" [](https://expedia.ca/Norfolk-Hotels-Norfolk-Waterside-Marriott.h14905.Hotel-Information) ![Hilton Vacation Club Oceanaire Virginia Beach](https://images.trvl-media.com/lodging/6000000/5200000/5190800/5190701/e4480049_y.jpg) ### Hilton Vacation Club Oceanaire Virginia Beach 10/10 Excellent "Clean, spacious, helpful staff & beautiful view of the ocean." [](https://expedia.ca/Virginia-Beach-Hotels-Oceanaire-By-Diamond-Resorts.h5190701.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 "Omg this is my 4th time staying here and i love it always clean and smells good and fresh and the service is truly amazing I'm from Jersey and i always visit my family down here and this js is my second home in Virginia " [](https://expedia.ca/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Boardwalk Resort and Villas](https://images.trvl-media.com/lodging/1000000/920000/910400/910351/7bb2cf2f_y.jpg) ### Boardwalk Resort and Villas 10/10 Excellent "Excellent service and well kept" [](https://expedia.ca/Virginia-Beach-Hotels-Boardwalk-Resort-And-Villas.h910351.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 - 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