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.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was CA $1,181, price is now CA $984 per person
CA $984
per person
Sep 13 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.4/10 Very good! (1,000 reviews)
Staff were friendly. Easy check in. Perfect location. The room was mostly clean. Hair in the corner of the bathroom z there was not cleaning service, I had to ask for extra towels as they were not replenished. Lots of flies at the outside restaurant…. Hard to eat our food. Room was cold

Reviewed on Aug 2, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was CA $1,358, price is now CA $1,021 per person
CA $1,021
per person
Sep 13 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
9.2/10 Wonderful! (1,916 reviews)
Loved our stay here. Will be coming back

Reviewed on Aug 2, 2026

The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Price was CA $2,032, price is now CA $1,722 per person
CA $1,722
per person
Sep 13 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
9.8/10 Exceptional! (37 reviews)
If we ever get the chance to come back to the Outer Banks we will stay here! The rooms are very clean and well appointed. The owner and staff were all kind and helpful and it’s close to everything. 5 stars all around!

Reviewed on Jul 30, 2026

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 $1,151, price is now CA $1,027 per person
CA $1,027
per person
Sep 1 - Sep 3
found 16 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Norfolk (ORF)
8.2/10 Very good! (1,340 reviews)
Great staff, amazing room. Very clean, shower water pressure and having plenty of hot water. The view is spectacular. Great location. Just wish the beds were a little bigger. But maybe I should loose some weight😅. Definitely will return again.

Reviewed on Aug 2, 2026

Days Inn by Wyndham Kill Devil Hills Oceanfront - Wilbur

Days Inn by Wyndham Kill Devil Hills Oceanfront - Wilbur

3.5 out of 5
Price was CA $1,264, price is now CA $1,135 per person
CA $1,135
per person
Sep 13 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)

Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
A wooden pier extending into a calm lake, surrounded by dense trees.

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

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 $88 per night from Aug 13 to Aug 14
CA $88
CA $104 total
Aug 13 - Aug 14
includes taxes & fees
7.2/10 Good! (913 reviews)
"Great place to stay. Staff was awesome and very clean."

Reviewed on Aug 1, 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $178 per night from Aug 9 to Aug 10
CA $178
CA $207 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (63 reviews)
"Beware you may not get a room! We booked and paid for 2 rooms on Wednesday. When we arrived late Friday we were told they were over booked and there were no rooms available. The staff was zero help, we were on our own. We had to scramble and find other accommodations in the middle of the night. My ..."

Reviewed on Aug 2, 2026

Hyatt Studios 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 $136 per night from Sep 1 to Sep 2
CA $136
CA $169 total
Sep 1 - Sep 2
includes taxes & fees
Wyndham Virginia Beach Oceanfront
See all 3,489 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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Beach Vacations
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Stay near popular Chesapeake attractions

A CVS store with a large archway and a red star logo.

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

View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

CA $158
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

CA $60
per adult
100% 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
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 $984 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.