Chesapeake Vacations from $707

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Your Chesapeake Vacation

Book a Chesapeake vacation package and get set for a fantastic getaway. Famous for its rich history and family-friendly attractions, there's lots to love about this city. You'll want to do a little exploring during your trip to Chesapeake. Make time for famous attractions like Greenbrier Mall, Chesapeake City Park and Oak Grove Lake Park. Don't delay visiting this city any longer. Your dream Chesapeake vacation is just a few clicks away with Expedia.

The Latest Chesapeake Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Colonial Inn Motel

Colonial Inn Motel

2 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
7.4/10 Good! (718 reviews)
Very courteous staff. Very clean facility. Parking kind of difficult.

Reviewed on May 14, 2024

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.8/10 Excellent! (1,833 reviews)
Close to a brewery and other dining options. Retro look.

Reviewed on May 14, 2024

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Jun 15 - Jun 22
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.6/10 Excellent! (1,010 reviews)
All the staff members are busy at their work and happy to work together. The management team is hiring the right people. The team members are also gracious to meet guests and do things guests like without the guests asking for those things to be done.

Reviewed on May 13, 2024

Four Sails Resort

Four Sails Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Jul 18 - Jul 23
Roundtrip non-stop flight included
Atlanta (ATL) to Norfolk (ORF)
9/10 Wonderful! (8 reviews)
This property is close to everything and the queen suite we booked offers balconies with great views of both the ocean and the city. The kitchen was nicely stocked and everything worked well. The bed was comfortable and the extra pillows and blanket were nice to have for snuggling on the couch. This is an older property so be prepared for the typical dated fixtures, furniture, and bath/kitchen design. If you don't mind the "not fancy" scene, I recommend the Four Sails Resort for its amazing location and friendly staff.

Reviewed on Dec 27, 2023

Sanderling Resort

Sanderling Resort

4 out of 5
Save 100% on your flight
per person
Jul 19 - Jul 23
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (364 reviews)
Quiet atmosphere with a lot of amenities, the gym was my personal favorite.

Reviewed on May 14, 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
4/5(438 area reviews)

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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

Chesapeake Hotel Deals

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 $127 per night from May 16 to May 17
$127
$147 total
includes taxes & fees
May 16 - May 17
8/10 Very Good! (1,007 reviews)
"This isn’t my first stay at this hotel. As always, the facility is clean, and the staff is very friendly. The spa tub is my favorite spot while the kids enjoy the indoor pool. We came here to celebrate Mother’s Day and a very happy momma I am!! Thank you!!"

Reviewed on May 12, 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 $98 per night from May 28 to May 29
$98
$114 total
includes taxes & fees
May 28 - May 29
8.6/10 Excellent! (807 reviews)
"Nice hotel, clean, very nice staff. Would stay again"

Reviewed on May 14, 2024

Fairfield Inn and Suites By Marriott Chesapeake
Delta Hotels by Marriott Virginia Beach Waterfront
Delta Hotels by Marriott Virginia Beach Waterfront
4 out of 5
2800 Shore Drive, Virginia Beach, VA
The price is $159 per night from May 19 to May 20
$159
$185 total
includes taxes & fees
May 19 - May 20
8.4/10 Very Good! (962 reviews)
You will not be Disappointed!
"Very clean and well put together"

Reviewed on May 12, 2024

Delta Hotels by Marriott Virginia Beach Waterfront
See all 3,702 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.

Explore other types of vacation packages

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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 $707. 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

4/5(260 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

4/5(76 reviews)

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

$126
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

$105
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

$38
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.