Find Historic Hotels in Chesapeake, VA

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Check availability on Chesapeake Historic Hotels

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

Our top choices for Chesapeake historic hotels

On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
8.8 out of 10, Excellent, (74 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is AED 951
AED 1,591 total
includes taxes & fees
14 Jun - 15 Jun
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Exterior detail

Beach Family Time Enjoy The Backyard Pool And Sunroom

Beach Family Time Enjoy The Backyard Pool And Sunroom
Virginia Beach
8.6 out of 10, Excellent, (36 reviews)
"Amazing property with a great host to help out. Amazing pool and great interior!"
United States
Devon W.
Beach Family Time Enjoy The Backyard Pool And Sunroom
Outdoor dining

Ground Floor 2 BR Cottage Walking to Everything!

Ground Floor 2 BR Cottage Walking to Everything!
Northeast Virginia Beach
9.2 out of 10, Wonderful, (63 reviews)
"Great stay "
United States
Brendan M.
The price is AED 1,158
AED 3,008 total
includes taxes & fees
7 Jun - 8 Jun
Ground Floor 2 BR Cottage Walking to Everything!
Property grounds

Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)

Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)
Northeast Virginia Beach
9.2 out of 10, Wonderful, (39 reviews)
"This was a cute house. It was in a great location for our needs. There were plenty of restaurants and shops within walking distance as well as the beach. "
United States
Lisa P.
The price is AED 913
AED 2,501 total
includes taxes & fees
7 Jun - 8 Jun
Upstairs 1BR Beach Apartment in the Heart of the Vibe District - 5 Minute Stroll to Beach (508B)
Exterior

Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)

Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (65 reviews)
"Great townhouse in a convenient location. It was the perfect place for weekend family getaway."
United States
Anonymous traveler
The price is AED 1,613
AED 3,967 total
includes taxes & fees
2 Jun - 3 Jun
Spacious 2 BR Townhouse Walking Distance to the Beach and Boardwalk (410B)
Property grounds

VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)

VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)
Northeast Virginia Beach
9.6 out of 10, Exceptional, (118 reviews)
"We enjoyed our stay. The townhouse was clean and comfortable. Easy walking distance to restaurants and boardwalk."
United States
Deborah S.
The price is AED 1,525
AED 3,839 total
includes taxes & fees
1 Jun - 2 Jun
VB Townhouse 2BR • Pet‑Friendly • Short Walk to Beach & Boardwalk (406B)
Property grounds

2 BR, 2 Story Townhouse by the Beach (410A)

2 BR, 2 Story Townhouse by the Beach (410A)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (71 reviews)
"The place was very clean, close to shops, gas stations, and the beach! We absolutely loved our stay here definitely would stay here again. The owners was nice to communicate back and forth with and answered instantly with anything you may need! Definitely a very clean and nice house to stay in!"
United States
Caitlyn W.
The price is AED 1,525
AED 3,839 total
includes taxes & fees
1 Jun - 2 Jun
2 BR, 2 Story Townhouse by the Beach (410A)
Exterior

Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)

Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)
Northeast Virginia Beach
9.4 out of 10, Exceptional, (73 reviews)
"Great location"
United States
Josh M.
The price is AED 1,588
AED 3,975 total
includes taxes & fees
1 Jun - 2 Jun
Newly Refreshed 2 BR Townhouse Walking Distance to the Beach and Boardwalk (406A)
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.
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Top Chesapeake Hotel Reviews

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

6/10 Okay
"This place has a great location, but needs work. Rooms were clean, but definitely need work - rust in the bathrooms, stained ceilings, outside of the building in disrepair in places (lots of crumbling at the edges of balconies). Hallways and elevatoes are dark and dingy in places. No USB outlets in the rooms. Pools are a nice amenity, but could also use with some cleaning and updating. The beach here is amazing- wide, clean, not crowded."
Kate 2-night trip
Posted less than an hour ago
Wyndham Virginia Beach Oceanfront

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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 romantic area.
How many historical hotels will I find in Chesapeake?
In Chesapeake, there are 115 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. In Chesapeake, booking a historic hotel doesn't mean you will stay in a place that's uncomfortable for guests or simply rundown.