Chesapeake Trips (flight + hotel)

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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
Greenbrier Mall

Greenbrier East

2 out of top 10 points of interest in this area

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Chesapeake City Park.

Find hotel + flight trips in Greenbrier East

Top hotels in Chesapeake

Comfort Suites Chesapeake - Norfolk
Comfort Suites Chesapeake - Norfolk
2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is P5,844 per night from 27 May to 28 May
P5,844
per night
27 May - 28 May
8.2/10 Very Good! (1,004 reviews)
Passing through
"Though the parking lot was having work done, you would have never known it coming into the hotel. We were welcomed with a smile. Our room was clean, hallways quite. We all had a very good night sleep. Breakfast was good, everything was hot. Coffee was amazing. I would definitely stay here again."

Reviewed on Apr 29, 2024

Comfort Suites Chesapeake - Norfolk
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 P8,623 per night from 13 May to 14 May
P8,623
per night
13 May - 14 May
8/10 Very Good! (972 reviews)
"Cons: Breakfast was extremely weak and limited. Pool was closed during spring break time. Hotel is aged and has many problems. Pros: Staff was professional and helpful."

Reviewed on Apr 22, 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
Fully refundableReserve now, pay when you stay
The price is P6,182 per night from 27 May to 28 May
P6,182
per night
27 May - 28 May
8.6/10 Excellent! (788 reviews)
"Clean room. Only thing I wasn’t a fan of were the pillows… a bit flat for my liking, other than that… staff was courteous and helpful. All staff encountered were Super friendly! The continental breakfast had tons of fresh options. We Felt very safe there. Would definitely stay there again in the ..."

Reviewed on Apr 28, 2024

Fairfield Inn and Suites By Marriott Chesapeake
See all 3,747 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 vacation 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 vacation 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 Center 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 neighborhood. 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 vacation?
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 vacation 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 vacation 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

Image for Greenbrier Mall

Greenbrier Mall

You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Greenbrier Mall
Image for Chesapeake Square Mall

Chesapeake Square Mall

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Image for Chesapeake Conference Center

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 theater scene.

Chesapeake Conference Center

What to do in Chesapeake

Image for Spirit of Norfolk Signature Dinner Cruise

Spirit of Norfolk Signature Dinner Cruise

P6,994
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

P5,810
Per adult
86% of travellers recommend
Spirit of Norfolk Signature Brunch Cruise
Image for Norfolk's Combo Pass - Battleship Wisconsin & Virginia Zoo

Norfolk's Combo Pass - Battleship Wisconsin & Virginia Zoo

P2,065
Per adult
100% of travellers recommend
Norfolk's Combo Pass - Battleship Wisconsin & Virginia Zoo
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.