Chesapeake Holidays

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Your Chesapeake Holiday

Pick a Chesapeake holiday package and you can prioritize what matters — enjoying yourself. No more planning hassles, just more free time to immerse yourself in the delights of this fascinating city, such as its rich history and family-friendly attractions. Eager to get out and explore? Greenbrier Mall, Chesapeake City Park and Chesapeake City Hall are just three of the most popular places to visit during a trip to Chesapeake. No matter your travel plans or the size of your budget, organising your ultimate tailored Chesapeake holiday is simple with Expedia.

Our guide on where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake

Chesapeake Holiday

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Jillians Billiards, Portlock Galleries at SoNo and Chesapeake City Park

Our pick of the best Chesapeake Hotel Deals

Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AU$145 per night from 16 Oct to 17 Oct
AU$145
16 Oct - 17 Oct
includes taxes & fees
6.8/10 (1,003 reviews)
"It was sufficient"

Reviewed on 1 Sept 2025

Red Roof Inn Chesapeake Conference Center
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AU$101 per night from 14 Oct to 15 Oct
AU$101
14 Oct - 15 Oct
includes taxes & fees
6.6/10 (596 reviews)
"Very nice and professional and very quick"

Reviewed on 6 Oct 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 2 Nov to 3 Nov
AU$153
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"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!"

Reviewed on 10 Oct 2025

Wingate by Wyndham Chesapeake
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.

What to do in Chesapeake

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.