Chesapeake Vacations from $708

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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.
Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
7.6/10 Good! (35 reviews)
Property could use a bit of power washing and some paint. Update to memory foam beds, update the appliances and it will be perfect.

Reviewed on May 5, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,781 reviews)
We stayed here during our honeymoon and our stay was exceptional. Comfy bed and pillows. Very friendly and helpful staff! This was our second stay at John Yancey and we enjoyed it.

Reviewed on Jun 27, 2025

Ocean Pines Resort

Ocean Pines Resort

3.5 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (119 reviews)
It was bigger than I expected and the bedrooms were separated from each other which I really appreciated. Kitchen had everything we needed and the larger bedroom had its own TV which was convenient. The bed was hard and the mattress cover nearly non existent. The top sheet came off each time I moved around. Be prepared for a lack of Wi Fi and lack of cell reception. It was alittle dated but I would definitely stay here again.

Reviewed on May 4, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,005 reviews)
It was ocean front with easy access to the beach. Has a nice bistro with good food. Close to stores and restaurants.

Reviewed on Jun 27, 2025

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (10 reviews)
Rooms are very nice. Like a studio apartment setup. Cozy and spacious. Beach is a very short walk away. Have plenty of restaurants, shops, and attractions nearby. Definitely going again in the future.

Reviewed on Jun 5, 2025

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Greenbrier Mall

Greenbrier East

1 out of top 10 points of interest in this area
4/5(438 area reviews)

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

Find hotels in Greenbrier East

Discover the most popular places to visit in Chesapeake

Greenbrier Mall

Greenbrier Mall

4/5(260 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.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

4/5(76 reviews)

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theater scene and great live music.

Chesapeake Conference Center

What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

$139
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

$40
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

Virginia Beach: Neptune Ghosts Haunted Walking Tour

$24
per adult
Virginia Beach: Neptune Ghosts Haunted Walking Tour
See all activities in Chesapeake

Chesapeake Hotel Deals

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
$229 nightly
The price is $265 total per night from Jul 6 to Jul 7
$265 total
Jul 6 - Jul 7
Total includes taxes and fees
8/10 Very Good! (1,018 reviews)
"Hotel location had a nice view of the beach and easy access to walk down onto the beach."

Reviewed on Jun 29, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG
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
$214 nightly
The price is $248 total per night from Jul 1 to Jul 2
$248 total
Jul 1 - Jul 2
Total includes taxes and fees
8.2/10 Very Good! (2,164 reviews)
"Great hotel amazing ocean views. Very clean. Only one thing is only 2 elevators that are very very slow. So if you’re on the top floors you’ll be waiting a while. Otherwise fantastic stay!"

Reviewed on Jun 29, 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
$206 nightly
The price is $239 total per night from Jul 2 to Jul 3
$239 total
Jul 2 - Jul 3
Total includes taxes and fees
8.2/10 Very Good! (1,010 reviews)
"The Surf Break Hotel was very clean and well kept but what really stood out was the excellent staff. From maintenance people, room cleaners, and waitresses in the Calypso, all were very good but the best was a desk man named Matt. He was very friendly, knowledgeable, helpful, and professional. I ..."

Reviewed on Jun 28, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
See all 3,414 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.

Find the Best Chesapeake Vacation Packages

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

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Frequently asked questions

How much does a Chesapeake vacation package cost?
You'll find cheap prices from $708 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.