Chesapeake Vacation Packages

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Your Chesapeake Vacation

Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

Top Chesapeake Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Seahorse Inn and Cottages

Seahorse Inn and Cottages

2.5 out of 5
per person
Aug. 4 - Aug. 11
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.8/10 Good! (662 reviews)
A great location. I appreciated the swift check-in.

Reviewed on May 20, 2024

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Aug. 4 - Aug. 11
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (1,007 reviews)
Clean, nice shower, great personnel

Reviewed on May 16, 2024

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Aug. 4 - Aug. 11
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.8/10 Excellent! (1,831 reviews)
Hotel was easy to find and conviently located to suit our plans. Very quiet. Staff pleasant.

Reviewed on May 22, 2024

Colonial Inn Motel

Colonial Inn Motel

2 out of 5
per person
Aug. 4 - Aug. 11
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.4/10 Good! (722 reviews)
The pool wasn’t even open

Reviewed on May 20, 2024

Travelodge by Wyndham Outer Banks/Kill Devil Hills

Travelodge by Wyndham Outer Banks/Kill Devil Hills

2 out of 5
per person
Aug. 4 - Aug. 11
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8/10 Very Good! (1,001 reviews)
Tanya at the front desk was wonderful!

Reviewed on May 19, 2024

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

Chesapeake Hotel Deals

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 CA $126 per night from May 29 to May 30
CA $126
CA $147 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (1,001 reviews)
"Very clean rooms. Breakfast was very good and staff was nice"

Reviewed on May 21, 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 CA $204 per night from May 26 to May 27
CA $204
CA $235 total
includes taxes & fees
May 26 - May 27
7.8/10 Good! (1,007 reviews)
"Nice, big rooms. Renovated, though some wear and tear around the edges. Pretty good breakfast. Lots of options: waffles, cereal, eggs, sausage, biscuits and gravy."

Reviewed on May 19, 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 CA $146 per night from May 27 to May 28
CA $146
CA $170 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (809 reviews)
"the staff was very helpful, checking in and out was simple, the hotel was keep very clean, would go back"

Reviewed on May 17, 2024

Fairfield Inn and Suites By Marriott Chesapeake
See all 3,688 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.

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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 CA $1,132. 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.

Discover the most popular places to visit in Chesapeake

Image for Greenbrier Mall

Greenbrier Mall

3.5/5(4 reviews)

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

CA $171
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

CA $142
Per adult
86% of travellers recommend
Spirit of Norfolk Signature Brunch Cruise
Image for Norfolk: Virginia Zoo & Battleship Wisconsin Combo Ticket

Norfolk: Virginia Zoo & Battleship Wisconsin Combo Ticket

CA $52
Per adult
74% of travellers recommend
Norfolk: Virginia Zoo & Battleship Wisconsin Combo Ticket
See all activities 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.