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.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was CA $1,704, price is now CA $1,340 per person
CA $1,340
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
7.8/10 Good! (1,408 reviews)
Great views of the ocean, pizza spot was great for a quick bite, sunsations right next door, complimentary coffee machine in the lobby, and right across from Waterman’s which is a fantastic restaurant. Will definitely stay here again!

Reviewed on Aug. 16, 2025

The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was CA $1,806, price is now CA $1,377 per person
CA $1,377
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.6/10 Excellent! (357 reviews)
It was an excellent place to stay. The staff was phenomenal. We did not have any issues at all. Their elevator was down, but they accommodated the residence extremely well. They had a staff member stay in the elevator and help residence to get to their floors. They did a great job in a really difficult situation. The view from the hotel is amazing The boardwalk outside is incredible. You just can’t get a better place to stay!

Reviewed on Jul. 22, 2025

Coastal Hotel and Suites Virginia Beach Oceanfront

Coastal Hotel and Suites Virginia Beach Oceanfront

2.5 out of 5
Northeast Virginia Beach
Price was CA $2,107, price is now CA $1,647 per person
CA $1,647
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.2/10 Wonderful! (1,199 reviews)
Enjoyed our oceanfront view and being able to walk to the beach in 5 minutes. Staff very friendly and hotel is clean. They are constantly cleaning up the sand and water messes left in the elevators and beach entrance lobby. Good breakfast and on site free parking in their parking garage.

Reviewed on Aug. 17, 2025

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 $1,747, price is now CA $1,372 per person
CA $1,372
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
7.8/10 Good! (1,005 reviews)
In general, the location of the hotel is excellent. However, the building is old, and most of the staff do not speak English, which makes communication difficult. The cleaning team also does not speak English, and unless you specifically ask them, they will not clean the room or restock the disposable cups and napkins. Additionally, the rooms do not have an electric kettle, which is a very basic necessity

Reviewed on Aug. 18, 2025

Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Central Newport News
Price was CA $1,679, price is now CA $1,369 per person
CA $1,369
per person
Oct 19 - Oct 25
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.8/10 Excellent! (551 reviews)
Check in was easy and the staff were incredibly friendly and helpful. The property isn’t perfect but it’s not as awful as some reviewers posted. It’s clean and comfortable. Perfect for a stay of a day or two.

Reviewed on Aug. 17, 2025

Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Default Image

Greenbrier East

1 out of top 10 points of interest in this area

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

Find hotels in Greenbrier East

Ready to book your vacation to Chesapeake?

 

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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 $73 per night from Aug 20 to Aug 21
CA $73
CA $86 total
Aug 20 - Aug 21
includes taxes & fees
6.4/10 (505 reviews)
Recommend
"Very pleasant 4 day stay in newly renovated room. Very clean and all staff was friendly."

Reviewed on Aug. 14, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 1 to Sep 2
CA $176
CA $205 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (2,249 reviews)
"Didn't have any good television stations or good movie channel"

Reviewed on Aug. 17, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Sep 14 to Sep 15
CA $140
CA $163 total
Sep 14 - Sep 15
includes taxes & fees
8.2/10 Very Good! (1,082 reviews)
"Great selection of shops & restaurants nearby. Helpful & friendly staff. Easy access to boardwalk & beach."

Reviewed on Aug. 17, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
See all 3,421 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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What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

CA $192
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

CA $56
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 $1,340 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.