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.
Buckroe Motel

Buckroe Motel

2 out of 5
Price was CA $1,411, price is now CA $1,327 per person
CA $1,327
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
5.6/10 (45 reviews)

The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
Price was CA $2,453, price is now CA $2,166 per person
CA $2,166
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
9/10 Wonderful! (240 reviews)
Beautiful room. Right on the golf course!

Reviewed on Oct 26, 2026

Charming Waterfront 3 Bedroom Cabin by RedAwning

Charming Waterfront 3 Bedroom Cabin by RedAwning

3 out of 5
Willoughby Spit
Price was CA $2,745, price is now CA $2,579 per person
CA $2,579
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
No reviews

Candlewood Suites Newport News/Yorktown by IHG

Candlewood Suites Newport News/Yorktown by IHG

2.5 out of 5
Central Newport News
Price was CA $1,625, price is now CA $1,534 per person
CA $1,534
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
8.4/10 Very good! (367 reviews)

Microtel Inn by Wyndham Newport News Airport

Microtel Inn by Wyndham Newport News Airport

2 out of 5
Central Newport News
Price was CA $1,448, price is now CA $1,368 per person
CA $1,368
per person
Dec 27 - Jan 2
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Norfolk (ORF)
7.2/10 Good! (1,000 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 $125 per night from Nov 10 to Nov 11
CA $125
CA $146 total
Nov 10 - Nov 11
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 $129 per night from Nov 15 to Nov 16
CA $129
CA $151 total
Nov 15 - Nov 16
includes taxes & fees
9.6/10 Exceptional! (270 reviews)
"They have everything you need, perfect for my weekend stay. It was clean and I felt safe as a solo traveler."

Reviewed on Oct 31, 2026

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 $180 per night from Nov 28 to Nov 29
CA $180
CA $210 total
Nov 28 - Nov 29
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Breakfast was average, we did have a couple roaches hanging out in the bathroom."

Reviewed on Nov 1, 2026

SpringHill Suites by Marriott Chesapeake Greenbrier
See all 3,531 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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All Inclusive Vacations
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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
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
Historic Norfolk Guided Walking Tour

Historic Norfolk Guided Walking Tour

CA $28
per adult
Historic Norfolk Guided Walking Tour
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 $1,327 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.