Find Historic Hotels in Chesapeake, VA

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Historic Hotels

Tonight
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Chesapeake Historic Hotels

Treetop Rustic Beach Front 2 Bedroom Apartment
Exterior

Treetop Rustic Beach Front 2 Bedroom Apartment

7.6 out of 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...
The price is AED 364
AED 1,004 total
includes taxes & fees
2 Oct - 3 Oct
Treetop Rustic Beach Front 2 Bedroom Apartment
Smithfield Inn
Exterior

Smithfield Inn

3.5 star property
9.0 out of 10, Wonderful, (96)
"Friendly staff Charming bed & breakfast nearby shops/dining convenient parking "
The price is AED 768
AED 860 total
includes taxes & fees
6 Oct - 7 Oct
Smithfield Inn
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV
On the beach

Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

7.8 out of 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. "
The price is AED 290
AED 721 total
includes taxes & fees
2 Oct - 3 Oct
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV
Norfolk Beach Cottage Rental
Fridge, microwave, oven, stovetop

Norfolk Beach Cottage Rental

9.0 out of 10, Wonderful, (273)
"To honor my elderly mothers request to go to the beach for a weekend, I looked for a small house that wasn't too expensive and where everything was on one floor. The cottage met our requirements. The cottage was clean, had ample towels, and the beds were comfortable. The check-in and out was very easy. The owners were very kind and pleasant to work with. We had a wonderful visit."
The price is AED 611
AED 1,469 total
includes taxes & fees
2 Oct - 3 Oct
Norfolk Beach Cottage Rental
Seashire Inn & Suites
View from property

Seashire Inn & Suites

2.0 star property
7.4 out of 10, Good, (356)
"Decent room for a pretty good price"
Seashire Inn & Suites
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
On the beach

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

9.0 out of 10, Wonderful, (66)
"House was exactly as described. Would most definitely stay there again and again! "
The price is AED 657
AED 1,198 total
includes taxes & fees
2 Oct - 3 Oct
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Breakers Resort Inn
Terrace/patio

Breakers Resort Inn

2.0 star property
7.6 out of 10, Good, (257)
"Good place to stay great location"
Breakers Resort Inn
Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!
Property grounds

Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!

10.0 out of 10, Exceptional, (39)
"Loved it so much 10/10 experience "
The price is AED 823
AED 1,202 total
includes taxes & fees
20 Oct - 21 Oct
Laid-Back Lakefront Luxury Near Bay & Beach: Welcome To Wiseacre!
Old Beach House Made New for Large Accommodations
Fridge, microwave, oven, stovetop

Old Beach House Made New for Large Accommodations

9.0 out of 10, Wonderful, (14)
"Pleasant stay for a quick trip to enjoy fishing. House had everything we needed. "
The price is AED 878
AED 2,583 total
includes taxes & fees
6 Oct - 7 Oct
Old Beach House Made New for Large Accommodations
Sheraton Norfolk Waterside Hotel
View from property

Sheraton Norfolk Waterside Hotel

3.5 star property
8.2 out of 10, Very Good, (1001)
"Excellent place to stay"
The price is AED 424
AED 498 total
includes taxes & fees
19 Oct - 20 Oct
Sheraton Norfolk Waterside Hotel
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

Top Chesapeake Hotel Reviews

Oceanfront Inn

Oceanfront Inn

10/10 Excellent
"My husband I were extremely pleased with the accommodations. The room was spacious and clean. The beds felt like they were brand new. Everyone one was so helpful from the front desk to the housekeeping staff. The ocean view balcony was just awesome. We spent a lot of time out there especially to watch the sunrise and catch some dolphins, which we did every morning. We highly recommend this place. If we come back to Virginia Beach this will be where we will be staying."
DEBBIE 4-night trip
Posted 1 day ago
Oceanfront Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 103 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.