Title: Book the Best HISTORIC Hotels in Chesapeake in 2025 | 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) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481121-Chesapeake-Square-Mall.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Chesapeake, VA from CA $92 ![](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 [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6612&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=6612&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=6612&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=6612&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chesapeake Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/49000000/48190000/48184200/48184136/3de6bcff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48190000/48184200/48184136/68a34741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48190000/48184200/48184136/9dd99f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48190000/48184200/48184136/49f8194e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treetop Rustic Beach Front 2 Bedroom Apartment Cottage Park 7.6/10 Good (26) "Repeat guest.. stayed in another unit previously \*loft property.Property is very close to the beach, can walk into the sand from the property. Pet friendly is a plus.. lots of doggos on the beach.Property has the basics.. minimal items in unit, so you need to bring quite a bit of things to make your trip complete. Owners have several units, so amenities are shared. Husband and I used the charcoal grill and set by the firepit in the sand. Not sure id stay in this particular unit again, but id... CA $125 CA $368 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Norfolk-Hotels-Treetop-Rustic-Beach-Front-2-Bedroom-Apartment.h48184136.Hotel-Information) ![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) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/94ec7af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed (Kitchen, Smoke Free)](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/fd2deafb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/197100/197069/8956dbdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof PLUS+ & Suites Virginia Beach – Seaside Northeast Virginia Beach 8.4/10 Very good (991) "This was in walking distance to the beach which was very nice. " CA $87 CA $116 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Virginia-Beach-Hotels-Rodeway-Inn-By-The-Beach.h197069.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/d0949374.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/db23ac04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/11ed3a1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Efficiency, Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/43300/43282/07dead87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Virginia Beach At The Beach Northeast Virginia Beach 7.8/10 Good (1011) "It was great bring within walking distance of restaurants. " CA $105 CA $124 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Virginia-Beach-Hotels-Days-Inn-By-Wyndham-Virginia-Beach-At-The-Beach.h43282.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/23000000/22630000/22624800/22624734/4912ecf9.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) ![Miscellaneous](https://images.trvl-media.com/lodging/23000000/22630000/22624800/22624734/8b01c36b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Smithfield Inn Smithfield 9.0/10 Wonderful (98) "Friendly staff Charming bed & breakfast nearby shops/dining convenient parking " CA $251 CA $281 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Smithfield-Hotels-Smithfield-Inn.h22624734.Hotel-Information) ![On the beach, white sand, beach cabanas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/8e60d2f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/373feea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sports facility](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/752209a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, beach views ](https://images.trvl-media.com/lodging/1000000/20000/12800/12727/f59437df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel Northeast Virginia Beach 8.4/10 Very good (1171) "Beach view was wonderful, on boardwalk with great restaurant!" CA $94 CA $111 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Virginia-Beach-Hotels-Surfbreak-Oceanfront-Hotel.h12727.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/93fd401c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/4009255e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/34000000/33560000/33556500/33556489/9e2198fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Norfolk Beach Cottage Rental East Ocean View 9.0/10 Wonderful (273) "The house was just the right size for 6 women ranging in ages 13-73. One bathroom was fine for all of us. The rooms were of good size and the fridge could fit so much food. Definitely would stay here again. " CA $233 CA $568 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Norfolk-Virginia-Beach-Hotels-Norfolk-Beach-Cottage-Rental.h33556489.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/57000000/56540000/56530200/56530177/32097970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/57000000/56540000/56530200/56530177/b08e5b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/57000000/56540000/56530200/56530177/728b91a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/57000000/56540000/56530200/56530177/1ba1723a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV Cottage Park 7.8/10 Good (16) "Love love love this place. Went for work, took 2 of my cats for company after work. It was a great place. It’s a studio set up, which was great. I’d stay here again for sure. " CA $111 CA $278 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Norfolk-Hotels-Beach-Side-Studio-3-Pet-Friendly.h56530177.Hotel-Information) ![Oceanfront, 1 King Bed Suite, 1 Sofa Bed, Accessible, Bathtub | Exterior](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/5cdda11b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/221462fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/3f753e45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/3000000/2830000/2820900/2820807/25ca8b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Virginia Beach-Oceanfront South Northeast Virginia Beach 8.8/10 Excellent (1017) "Very nice stay" CA $165 CA $193 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Virginia-Beach-Hotels-Hampton-Inn-Virginia-Beach-Oceanfront-South.h2820807.Hotel-Information) ![Balcony view](https://images.trvl-media.com/lodging/2000000/1620000/1614400/1614389/b0796a4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1620000/1614400/1614389/f819482d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1620000/1614400/1614389/02a110e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1620000/1614400/1614389/2cb7cef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Barclay Towers Resort Hotel Northeast Virginia Beach 8.0/10 Very good (1005) "Clean room, friendly staff members, beach view " CA $110 CA $150 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Virginia-Beach-Hotels-The-Barclay-Towers-Resort-Hotel.h1614389.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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/bd5a9850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/3000000/2760000/2759000/2758929/ba60c7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seashire Inn & Suites Northeast Virginia Beach 7.4/10 Good (361) "Decent room for a pretty good price" CA $59 CA $92 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Virginia-Beach-Hotels-Seashire-Inn-Suites.h2758929.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=2025-10-28&endDate=2025-10-29®ionId=6612&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chesapeake Hotel Reviews ![Holiday Inn & Suites Virginia Beach North Beach by IHG](//images.trvl-media.com/lodging/1000000/20000/16300/16268/631516bd_y.jpg) ### Holiday Inn & Suites Virginia Beach North Beach by IHG 10/10 Excellent "Great place to stay right on the beach." [](https://expedia.ca/Virginia-Beach-Hotels-Holiday-Inn-Suites-Virginia-Beach-North-Beach.h16268.Hotel-Information) ![Oceans 2700](//images.trvl-media.com/lodging/6000000/5480000/5479500/5479442/a7a4bc43_y.jpg) ### Oceans 2700 10/10 Excellent "I enjoyed a one night stay on a rainy September Saturday. The hotel was great. The building has been there for decades so it is old, but perfectly maintained, newer appliances and fixtures, immaculately clean. The room wasn't super big especially with two queen beds in, but big enough to shower sleep and chill. It's VB oceanfront so dozens of food beverage and shopping options within blocks. One block from the beach. Lots of convenience stores but only one full grocery store in the area and it's about three blocks away from this hotel so that was great. There's a small pool, barely any lobby to speak of or other common areas. Just a door to a balcony, the steps are outside as well but right next to the parking." [](https://expedia.ca/Virginia-Beach-Hotels-Oceans-2700.h5479442.Hotel-Information) ![Oceanfront Inn](//images.trvl-media.com/lodging/3000000/2100000/2094900/2094819/05b11887_y.jpg) ### Oceanfront Inn 10/10 Excellent "The staff are some of the kindest most helpful and patient people you could ever want to meet. The rooms are roomy! Great balconies, all face the water. The rooms I've had there were always quiet with working fridge, TV, AC, etc. Very comfortable mattresses. Plenty of hot water for showers (that's a concern at a busy beach). Price/value cannot be beat. Not even with a stick!" [](https://expedia.ca/Virginia-Beach-Hotels-Oceanfront-Inn.h2094819.Hotel-Information) ![DoubleTree by Hilton Virginia Beach](//images.trvl-media.com/lodging/1000000/20000/12400/12372/w3837h2558x3y3-2be8c9fa_y.jpg) ### DoubleTree by Hilton Virginia Beach 10/10 Excellent "Everything was spic and span clean. Very nice hotel. Would stay again. " [](https://expedia.ca/Virginia-Beach-Hotels-DoubleTree-By-Hilton-Virginia-Beach.h12372.Hotel-Information) ![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA](//images.trvl-media.com/lodging/1000000/10000/5400/5363/c80e2694_y.jpg) ### Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA 10/10 Excellent "The remodeled rooms are really nice. I got a good breakfast everyday. I love that I can park on the floor where my room is. It makes loading and unloading my car so easy. " [](https://expedia.ca/Virginia-Beach-Hotels-Country-Inn-Suites-By-Radisson.h5363.Hotel-Information) ![Wingate by Wyndham Chesapeake](//images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/d607b035_y.jpg) ### Wingate by Wyndham Chesapeake 10/10 Excellent "Stayed overnight because my flight was canceled, and I must say this hotel was one of the best in terms of room space and comfort. I would highly recommend this hotel!" [](https://expedia.ca/Chesapeake-Hotels-Wingate-By-Wyndham-Chesapeake.h1513238.Hotel-Information) ![Hilton Vacation Club Ocean Beach Club Virginia Beach](//images.trvl-media.com/lodging/2000000/1370000/1367400/1367330/b6b50f9a_y.jpg) ### Hilton Vacation Club Ocean Beach Club Virginia Beach 10/10 Excellent "Beach view was exceptional with sunrise jets flying over see pool perfect and comfortable balcony and room, all." [](https://expedia.ca/Virginia-Beach-Hotels-Ocean-Beach-Club-By-Diamond-Resorts.h1367330.Hotel-Information) ![STUDIOS & SUITES 4 LESS CHESAPEAKE ](//images.trvl-media.com/lodging/1000000/50000/40500/40428/e945abb1_y.jpg) ### STUDIOS & SUITES 4 LESS CHESAPEAKE 10/10 Excellent "Staff was friendly. The rooms were comfortable and the price was acceptable. Thank you for the stay. " [](https://expedia.ca/Chesapeake-Hotels-Econo-Lodge-Chesapeake-Route-13-And-I-464.h40428.Hotel-Information) ![Holiday Inn Va Beach-Oceanside (21st St) by IHG](//images.trvl-media.com/lodging/1000000/10000/4900/4857/9b6817bb_y.jpg) ### Holiday Inn Va Beach-Oceanside (21st St) by IHG 10/10 Excellent "Great view of the ocean, and the room was very clean and comfortable. The lack of parking would be the only con that I can think of." [](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? > The historical places in Chesapeake are likely a big part of your travel plans. And while you're here, you can visit the array of shops and popular beaches. And also relish a stop at the top-notch restaurants in this family-friendly area. ### How many historical hotels will I find in Chesapeake? > In Chesapeake, there are 104 hotels and other accommodations bookable on Expedia though you won't find many designated historic hotels. ### What are the must-see historical places and other sights to visit in Chesapeake? > Favorite places to visit include Greenbrier Mall, Chesapeake Conference Center, and Chesapeake Square Mall. Additionally, in the area you'll find Naval Station Norfolk and Sandbridge Beach. ### What is a historic hotel like in Chesapeake? > Historic hotels give guests an opportunity to stay in a place that's been recognized with an official historic designation. Historic hotels throughout the world come in all forms like castles, palaces, grand homes or even old police stations, pubs, lodges or skyscrapers. These types of hotels in Chesapeake usually retain authentic elements such as period features or traditional architecture in guestrooms or communal 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 focus on the architecture and actual building. Mainly heritage hotels draw meaning from the cultural value and how it inspired the community. ### Do historic hotels in Chesapeake have modern facilities? > Yes. Every effort is made to preserve treasured traditions and historic facades, but hotel interiors are fitted with modern conveniences and safety features. Guests should expect the popular amenities you'd get from a hotel such as private rooms with updated bathroom facilities, WiFi, and more. 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