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.
Days Inn by Wyndham Hampton Near Coliseum Convention Center

Days Inn by Wyndham Hampton Near Coliseum Convention Center

2 out of 5
Coliseum Central
per person
Oct 2 - Oct 9
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
5.8/10 (1,006 reviews)
Close to several beaches and activities. Decently priced

Reviewed on Jul. 17, 2025

Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Central Newport News
per person
Oct 2 - Oct 9
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
8.8/10 Excellent! (543 reviews)
Great staff. The hotel is conveniently surrounded by restaurants and retail stores.

Reviewed on Jul. 3, 2025

The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
per person
Oct 2 - Oct 9
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
9/10 Wonderful! (171 reviews)
Clean, quiet and convenient.

Reviewed on Jul. 8, 2025

La Quinta Inn & Suites by Wyndham Norfolk

La Quinta Inn & Suites by Wyndham Norfolk

3 out of 5
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
7.8/10 Good! (1,010 reviews)
Overall good stay but we did see some cockroaches.

Reviewed on Jul. 25, 2025

Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
Downtown Norfolk
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
6.4/10 (1,008 reviews)
The elevator wasn't working and a/c leaks

Reviewed on Jul. 29, 2025

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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Greenbrier

4 out of top 10 points of interest in this area

If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.

Find hotels in Greenbrier

Ready to book your vacation to Chesapeake?

 

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Chesapeake Hotel Deals

Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Aug 3 to Aug 4
CA $104
CA $123 total
Aug 3 - Aug 4
includes taxes & fees
7/10 Good! (1,001 reviews)
"It was affordable and within a good range of everything needed. The staff was welcoming."

Reviewed on Jul. 28, 2025

Red Roof Inn Chesapeake Conference Center
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is CA $73 per night from Jul 31 to Aug 1
CA $73
CA $86 total
Jul 31 - Aug 1
includes taxes & fees
6.4/10 (482 reviews)
"😍"

Reviewed on Jul. 28, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
3900 Atlantic Avenue, Virginia Beach, VA
The price is CA $284 per night from Aug 24 to Aug 25
CA $284
CA $329 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,086 reviews)
"Great experience. Desk staff and others were super friendly. Cannot ask for more."

Reviewed on Jul. 27, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG
See all 3,437 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
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What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

CA $172
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

CA $55
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

CA $33
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
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 $1,025 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.