Chesapeake Vacations from $276

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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.

The Latest Chesapeake vacation packages

Price found within the past 48 hours. Click for updated prices.
Beach Quarters Resort
Sanderling Resort Residences
John Yancey Oceanfront Inn
Boardwalk Resort and Villas
Sea Ranch Resort
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See all available trips from Columbus to Chesapeake
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Where to stay in Chesapeake

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

Discover the most popular places to visit in Chesapeake

What to do in Chesapeake

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
$59 nightly
The price is $69 total per night from Aug 21 to Aug 22
$69 total
Aug 21 - Aug 22
Total includes taxes and fees
6.4/10 (510 reviews)
Quaint
"It was quiet for having renovations going on, we feally didnt get settled til about 1ca.m. we attended a concert"

Reviewed on Aug 17, 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
$128 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total includes taxes and fees
8.2/10 Very Good! (2,243 reviews)
"Great"

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
$101 nightly
The price is $118 total per night from Sep 14 to Sep 15
$118 total
Sep 14 - Sep 15
Total includes taxes and 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
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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Frequently asked questions

How much does a Chesapeake vacation package cost?
You'll find cheap prices from $276 on Expedia for your Chesapeake escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
December, January and February are great times to look for cheap Chesapeake vacation packages. Choosing to travel in less busy months means you can typically find lower prices on flights and accommodations.
How many days is enough for Chesapeake?
Chesapeake vacations can be short or long, but to really get a feel for this destination, we'd say 2 days is about right. In this timeframe, you can visit major attractions like Chesapeake City Park and Oak Grove Lake Park as well as underrated spots. Don't miss out on cool neighborhoods such as Greenbrier East and Greenbrier West either. If you're smart with your time, you can even schedule a day trip outside of Chesapeake too.
Is it worth booking a vacation package to Chesapeake?
Chesapeake has all the ingredients you need for a fantastic break — history, nature and hiking are just the start. Whether you want to visit sights like Oak Grove Lake Park and Portlock Galleries at SoNo, or take the path less traveled, you'll have plenty to see and do on your Chesapeake vacation.
How to find the best Chesapeake package deals?
Begin your search for a Chesapeake package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesapeake package deal right away, just tweak your dates and search again. Keep in mind 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 next Chesapeake retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesapeake?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Chesapeake break.
How to plan a trip to Chesapeake?

  1. Choose when to get away: Check your diary and get your bags packed. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Chesapeake.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to Chesapeake.
  3. Use Expedia's trip planning tool to discover Chesapeake: Research every aspect of your trip to Chesapeake with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Chesapeake. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Chesapeake vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some fun things to do in Chesapeake. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Chesapeake vacation packages?
Your Chesapeake getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.