Chesapeake 2024 Holidays

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Where to stay in Chesapeake

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

2 out of top 10 points of interest in this area
3.5/5(2 area reviews)

If you're spending some time in Greenbrier East, Greenbrier Mall and Chesapeake City Park are top sights worth seeing.

Find hotels in Greenbrier East

Top hotels in Chesapeake

Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
The price is €134 per night from 1 Jul to 2 Jul
€134
per night
1 Jul - 2 Jul
8.6/10 Excellent! (2,449 reviews)
Affordable and convenient
"Great location off the boardwalk. Affordable and convenient. AC was a bit challenged couldn’t get the room under 70 degrees."

Reviewed on 17 Jun 2024

Schooner Inn
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 €140 per night from 23 Jun to 24 Jun
€140
per night
23 Jun - 24 Jun
8/10 Very Good! (1,003 reviews)
"The hot tub wasn’t hot and jets were nonexistent. Nothing you can do about guests being loud in building but in parking lot there were loud music from vehicles. Which was ok. It was sent late."

Reviewed on 15 Jun 2024

Wingate by Wyndham Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
Fairfield Inn and Suites By Marriott Chesapeake
2.5 out of 5
1560 Crossways Blvd, Chesapeake, VA
The price is €135 per night from 30 Jun to 1 Jul
€135
per night
30 Jun - 1 Jul
8.8/10 Excellent! (838 reviews)
"I was very impressed with this hotel. The room was comfortable and clean. The staff was friendly, especially the woman from Canada that checked us in. The gym was clean and had an adequate amount of equipment for me to use for my workouts. The breakfast was delicious. I would definitely return if ..."

Reviewed on 17 Jun 2024

Fairfield Inn and Suites By Marriott Chesapeake
See all 3,662 properties in 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.

Frequently asked questions

How much does a Chesapeake holiday package cost?
Get your credit card ready, because a trip to Chesapeake starts from a tempting . When you combine your hotels, flights and car rentals into a travel package, you’ll walk away with the best prices.
How do I get a cheap travel package to Chesapeake?
If you love bargains, bundle your bookings into a Chesapeake holiday package. Whether you need hotels, flights, tours or rental cars, you can browse and book everything in one place. You’ll have lots of choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 hotels around the world to select from. Fly with who you want, find a room where you like and save precious dollars — now that’s the ideal escape!
Where should I stay in Chesapeake?
With loads to explore in Chesapeake, it makes sense to book a room in a hotel near its attractions. Greenbrier Mall, Chesapeake Square Mall and Chesapeake Regional Medical Centre are some good ones to add to your must-see list.
What are the top hotels in Chesapeake?
Many visitors to Chesapeake often stay in Greenbrier East. Hyatt Place Chesapeake and Aloft Chesapeake are well-liked options in this neighbourhood. But it’s not the only exciting place around town! Western Branch North is also a fantastic area and where you’ll find Comfort Suites Chesapeake - Norfolk and Wingate by Wyndham Chesapeake.
How far in advance should I book my Chesapeake holiday?
Reserving your seat early with Expedia means one less thing to worry about. Many air carriers advertise tickets up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, great deals to Chesapeake sometimes become available just a few weeks before departure.
What does an Expedia Chesapeake travel package include?
From flights and hotels to rental cars, Expedia can help you put together a Chesapeake package that works for you. Heading away for a week or two? Consider a rental car, hotel and flight bundle. If your break is short, a flight and hotel deal could be more your style. Experiences can also be added after you’ve booked. Our packages make it easy to save and plan.
What should I know before booking a Chesapeake travel package?
A package can be easier on the bank balance than individually booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save a pretty penny. Whatever kind of holiday you’re planning, you’re bound to find a package that suits your budget.
If I'm not able to travel, can I cancel my Chesapeake holiday package?
If your travel plans in Chesapeake have been upended, it’s good to know that you can cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge fees. For more information, visit our Customer Service Portal.

Popular places to visit

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Greenbrier Mall

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.

Greenbrier Mall
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Chesapeake Square Mall

You can search for that perfect souvenir at Chesapeake Square Mall during your visit to Chesapeake. Discover the top-notch restaurants and acclaimed theatre scene in this family-friendly area.

Chesapeake Square Mall
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Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theatre scene.

Chesapeake Conference Center

What to do in Chesapeake

Image for Spirit of Norfolk Signature Dinner Cruise

Spirit of Norfolk Signature Dinner Cruise

€82
Per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Image for Spirit of Norfolk Signature Brunch Cruise

Spirit of Norfolk Signature Brunch Cruise

€97
Per adult
86% of travellers recommend
Spirit of Norfolk Signature Brunch Cruise
Image for Norfolk's Passport to Fun Admission Tickets and Savings

Norfolk's Passport to Fun Admission Tickets and Savings

€34
Per adult
100% of travellers recommend
Norfolk's Passport to Fun Admission Tickets and Savings
See all activities in Chesapeake

More trip options

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