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.
Mulberry Inn

Mulberry Inn

2.5 out of 5
North Newport News
per person
Oct 19 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Norfolk (ORF)
7.6/10 Good! (697 reviews)
It was clean enough

Reviewed on Aug. 4, 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 19 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Norfolk (ORF)
8.8/10 Excellent! (548 reviews)
Very nice except for some doors were not working in the parking area to the hotel and also the bed was not so comfortable but everything else was nice

Reviewed on Aug. 3, 2025

Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
7.6/10 Good! (36 reviews)
Great balcony with a great view

Reviewed on Aug. 2, 2025

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 19 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Norfolk (ORF)
5.8/10 (1,006 reviews)
Close to several beaches and activities. Decently priced

Reviewed on Jul. 17, 2025

Sunrise Inn By OYO Newport News US-60

Sunrise Inn By OYO Newport News US-60

2.5 out of 5
North Newport News
per person
Oct 19 - Oct 26
found 13 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Norfolk (ORF)
4.8/10 (200 reviews)
We stayed for one night to be close to the fields for a softball tournament. It was fine for what we needed it for

Reviewed on Jun. 5, 2022

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?

 

Choose your dates

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 10 to Aug 11
CA $104
CA $123 total
Aug 10 - Aug 11
includes taxes & fees
7/10 Good! (1,003 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 Aug 6 to Aug 7
CA $73
CA $86 total
Aug 6 - Aug 7
includes taxes & fees
6.4/10 (484 reviews)
"Great"

Reviewed on Jul. 31, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Sep 1 to Sep 2
CA $125
CA $156 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,584 reviews)
"Loved it!"

Reviewed on Jul. 31, 2025

Wyndham Virginia Beach Oceanfront
See all 3,429 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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Beach Vacations
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What to do in Chesapeake

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
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
View of Spirit of Norfolk

Spirit of Norfolk Signature Brunch Cruise

CA $152
per adult
86% of travellers recommend
Spirit of Norfolk Signature Brunch Cruise
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 $1,007 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.