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.
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
per person
Jul. 12 - Jul. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8/10 Very Good! (1,003 reviews)
Zakir is the best. Polite, friendly, helpful, and accommodating.

Reviewed on May 27, 2024

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Aug. 5 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.6/10 Excellent! (1,007 reviews)
mats with curled ends in front of beach access. very dangerous

Reviewed on May 28, 2024

Sanderling Resort

Sanderling Resort

4 out of 5
Save 100% on your flight
per person
Aug. 5 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.8/10 Excellent! (366 reviews)
Great beach access. Rooms could be a little cleaner.

Reviewed on May 27, 2024

Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
per person
Jul. 12 - Jul. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
7.2/10 Good! (1,013 reviews)
I liked the proximity to the ocean and the comfortable bed.

Reviewed on May 25, 2024

Travelodge by Wyndham Virginia Beach

Travelodge by Wyndham Virginia Beach

2 out of 5
Northeast Virginia Beach
per person
Jul. 12 - Jul. 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
5.4/10 (570 reviews)
The price was very good for it being literally across the street from the beach/boardwalk. The hotel staff were very nice, check in was a breeze when we got there. The pool didnt seem too inviting and we never seen anyone in there..but your at the beach so we hadnt planned to use the pool anyway lol. The room wasnt terrible, especially considering the price but it could have been cleaned better. We could see the dirt/sand on the floor when we first got there. The bathroom however was cleaned good, the beds were clean also. Its not like crack head central there either so that was a big plus! Id stay again

Reviewed on Aug. 26, 2023

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 $161 per night from Jun. 4 to Jun. 5
CA $161
CA $187 total
includes taxes & fees
Jun 4 - Jun 5
8.2/10 Very Good! (1,001 reviews)
"Great"

Reviewed on May 28, 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 $195 per night from May 29 to May 30
CA $195
CA $226 total
includes taxes & fees
May 29 - May 30
7.8/10 Good! (1,004 reviews)
"My room was clean, towels were fresh and soft, the bed was comfy and it was nice and quiet."

Reviewed on May 25, 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 CA $155 per night from May 29 to May 30
CA $155
CA $180 total
includes taxes & fees
May 29 - May 30
8.6/10 Excellent! (813 reviews)
NEEDS BETTER MATTRESSES!
"The damn bed was old and horrible to sleep on! Springs poking us all night and the pillows were as flat as tortillas. We both woke several times and ended up leaving early. Other than that the room was clean and appeared to have been recently updated. Staff was very friendly and accommodating."

Reviewed on May 27, 2024

Fairfield Inn and Suites By Marriott Chesapeake
See all 3,694 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $940. 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

Other vacations you might like

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