Chesapeake City County Holidays

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Top destinations in Chesapeake City County

Top hotels in Chesapeake City County

Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
The price is S$95 per night from 26 Feb to 27 Feb
S$95
includes taxes & fees
26 Feb - 27 Feb
8.6/10 Excellent! (2,914 reviews)
"Love the location on oceanfront near where all the surfers surf - great boardwalk right there fir walk next to ocean. Good restaurants near by. Staff friendly and efficient."

Reviewed on 14 Feb,2025

Schooner Inn
Hyatt Place Virginia Beach / Oceanfront
Hyatt Place Virginia Beach / Oceanfront
3 out of 5
3601 ATLANTIC AVENUE, 36TH AND ATLANTIC, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 4 Mar to 5 Mar
S$149
includes taxes & fees
4 Mar - 5 Mar
9.2/10 Wonderful! (1,594 reviews)
"Room was very quiet. We didn't hear anything from rooms besides us or above us. Comfortable beds, good bedding for pullout bed. Good breakfast options, and my dairy-free family appreciated the oat milk option for cereal. Vehicle was ready on time from valet service."

Reviewed on 15 Feb,2025

Hyatt Place Virginia Beach / Oceanfront
Hilton Vacation Club Oceanaire Virginia Beach
Hilton Vacation Club Oceanaire Virginia Beach
3.5 out of 5
3421 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is S$219 per night from 23 Feb to 24 Feb
S$219
includes taxes & fees
23 Feb - 24 Feb
8/10 Very Good! (1,009 reviews)
"Great property!"

Reviewed on 16 Feb,2025

Hilton Vacation Club Oceanaire Virginia Beach
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.

* 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.