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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was CA $1,792, price is now CA $1,472 per person
CA $1,472
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Norfolk (ORF)
8.8/10 Excellent! (1,003 reviews)
I will tell friend and revisit

Reviewed on Nov 8, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Northeast Virginia Beach
Price was CA $1,952, price is now CA $1,572 per person
CA $1,572
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Norfolk (ORF)
8/10 Very good! (1,584 reviews)

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was CA $2,048, price is now CA $1,708 per person
CA $1,708
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Norfolk (ORF)
8.2/10 Very good! (1,447 reviews)

The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was CA $1,982, price is now CA $1,675 per person
CA $1,675
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Norfolk (ORF)
7.8/10 Good! (1,002 reviews)
Cool stay. Staff was very cool.

Reviewed on Nov 2, 2026

The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was CA $2,125, price is now CA $1,807 per person
CA $1,807
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Sudbury (YSB) to Norfolk (ORF)
9.2/10 Wonderful! (57 reviews)

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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Deep Creek South

1 out of top 10 points of interest in this area

Suburban community with a rural touch, Deep Creek is connected to the historic Dismal Swamp Canal, a National Historic Civil Engineering Landmark. Located along the original U.S. Highway 17 route, it offers easy access to nearby attractions.

Find hotels in Deep Creek South

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Chesapeake Hotel Deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is CA $119 per night from Dec 7 to Dec 8
CA $119
CA $140 total
Dec 7 - Dec 8
includes taxes & fees
Comfort Suites Chesapeake - Norfolk
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Nov 13 to Nov 14
CA $130
CA $152 total
Nov 13 - Nov 14
includes taxes & fees
YourSpace Hotels Chesapeake
SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier

3 out of 5
1446 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Nov 12 to Nov 13
CA $175
CA $204 total
Nov 12 - Nov 13
includes taxes & fees
SpringHill Suites by Marriott Chesapeake Greenbrier
See all 3,431 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

Stay near popular Chesapeake attractions

A large building with a prominent arched entrance and a green roof.

Greenbrier Mall

8.4/10 (837 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.
See properties

What to do in Chesapeake

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

CA $60
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

CA $118
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Ziplining and Climbing at The Adventure Park at Virginia Aquarium

Ziplining and Climbing at The Adventure Park at Virginia Aquarium

CA $90
per adult
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
See all activities in Chesapeake

Frequently asked questions

How much does a Chesapeake vacation package cost?
You can snap up a vacation package to this destination from CA $1,472 on Expedia. However, how much your vacation to Chesapeake costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chesapeake?
You can generally find reduced prices and better availability in January, February and November. Explore our cheap Chesapeake vacation packages and you could get some great off-season deals.
How many days is enough for Chesapeake?
With about 2 days, you'll have plenty of time to visit popular neighbourhoods such as Greenbrier East and Greenbrier West during your Chesapeake vacation. Be sure to also add Chesapeake Central Library and Portlock Galleries at SoNo to your sightseeing list. In the mood for more adventures? Consider venturing outside of Chesapeake on day trips and tours.
Is it worth booking a vacation package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake vacation is a hit with all kinds of visitors. Be sure to check out major sights like Portlock Galleries at SoNo and Oak Grove Lake Park, and consider renting some wheels for day trips to discover even more.
How to find the best Chesapeake package deals?
Start your search for a Chesapeake package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Chesapeake package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chesapeake adventure off to a flying start.
Is it cheaper to book a Chesapeake vacation as a package?
You can enjoy significant savings on your Chesapeake escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake?
If you have your Chesapeake vacation dates finalized, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Chesapeake?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chesapeake.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chesapeake.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Chesapeake vacation package that brings all your bookings together.

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