Chesapeake City County Holidays

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Top destinations in Chesapeake City County

A golf course, a large building complex, and a marina by a river.
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Chesapeake

Chesapeake

Top hotels in Chesapeake City County

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is S$126 per night from 29 Nov to 30 Nov
S$126
29 Nov - 30 Nov
includes taxes & fees
9/10 Wonderful! (1,144 reviews)
"Clean room, breakfast, parking"

Reviewed on 29 Oct, 2026

Comfort Suites Chesapeake - Norfolk
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is S$130 per night from 8 Nov to 9 Nov
S$130
8 Nov - 9 Nov
includes taxes & fees
9.6/10 Exceptional! (268 reviews)
"Loved having a washer and dryer, super convenient. The staff was so friendly and the room was very comfortable. The sheets had some stains on them and the staff were prompt and apologetic on the issue."

Reviewed on 29 Oct, 2026

YourSpace Hotels Chesapeake
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
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Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel
See all 3,546 properties in Chesapeake City County
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.

Frequently asked questions

How much does a Chesapeake City County holiday package cost?
Perhaps less than you might think — from just , actually! By bundling hotels, flights and car rentals into a custom-built package, your getaway to Chesapeake City County is just clicks away.
How do I get a cheap travel package to Chesapeake City County?
Find flights that suit your schedule, add a hotel to your booking and watch the savings rack up with a Chesapeake City County holiday package. It's as easy as that! From flights and hotels to activities and rental cars, Expedia makes travelling on a budget easy. And with over 550 partner airlines and 1,000,000 properties globally to choose from, you'll never be short of choice.
What are the top hotels in Chesapeake City County?
Hyatt Place Chesapeake and Aloft Chesapeake are a couple of welcoming options in Chesapeake. A key stop on any good Chesapeake City County itinerary, we recommend taking the time to really explore this impressive city.
How far in advance should I book my Chesapeake City County holiday?
Search Expedia to compare international airfares as soon as you've got your travel dates. You can normally purchase a seat up to 12 months before departure. If you can't see your preferred air carrier, or you've left things to the last moment, fear not. Cheap tickets to Chesapeake City County occasionally appear within weeks of departure.
What does an Expedia Chesapeake City County travel package include?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add activities and experiences. Want to pick your fare class? That's also possible. The choice is all yours when it comes to putting together your dream Chesapeake City County getaway.
What should I know before booking a Chesapeake City County travel package?
Booking all the parts of your escape together is a smart way to save. Combine your car rentals, flights and hotels into a handy little package. But you're not limited to hotels. Expedia offers all sorts of properties, including holiday rentals such as beach villas and city residences. The list is almost endless!
Can I choose my airline with a Chesapeake City County Expedia holiday package?
Expedia offers access to more than 550 airline partners globally, so you sure can! Just select your preferred carrier and craft your ideal Chesapeake City County trip.
If I'm not able to travel, can I cancel my Chesapeake City County holiday package?
If your holiday plans in Chesapeake City County have changed, it's a relief to know that it is possible to cancel your booking. If you booked in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a cancellation fee. For more details, check our Customer Service Portal.

Stay near popular Chesapeake City County attractions

A large building with a prominent arched entrance and a green roof.

Greenbrier Mall

8.4/10 (837 reviews)
You can search for that perfect souvenir at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.
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What to do in Chesapeake City County

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

S$54
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Ziplining and Climbing at The Adventure Park at Virginia Aquarium

Ziplining and Climbing at The Adventure Park at Virginia Aquarium

S$82
per adult
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

S$31
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
See all activities in Chesapeake City County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.