How much does a Chesapeake vacation package cost?

You'll find cheap prices from $312 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?

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. 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. 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. 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. 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. 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.

Discover Chesapeake Vacation Packages - Book from $312

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.

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

$312

per person

Apr 4 - Apr 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.6/10 Excellent! (1,003 reviews)

Overall a great stay! There for only one night. Staff was outstanding! Room was clean and did not have an odor. Light in the bedroom did not come on with switch. Thought I was getting an oceanfront room but it was actually on the side of the hotel. I could see the ocean but on if I went to the window. No comment on the other amenities bc we didn't use them. Will definitely stay again!

Reviewed on Jan 19, 2026

Sanderling Resort Residences

Save 100% on your flight

$2,128

per person

Apr 2 - Apr 8

found 13 hours ago

Roundtrip flight included

Islip (ISP) to Norfolk (ORF)

No reviews

Budget Inn Norfolk Va

Willoughby Spit

Save 100% on your flight

$1,099

per person

Apr 1 - Apr 6

found 9 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

5.8/10 (369 reviews)

Management guarantees safety thats most important. There are plenty of restaurants around to choose from. The beach view is beautiful, and the walk to the beach is not gar at all. I enjoy being here. Im from a different state.

Reviewed on Jan 5, 2026

TRU by Hilton Chesapeake, VA

Greenbrier

Save 100% on your flight

$453

per person

Mar 13 - Mar 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.6/10 Excellent! (329 reviews)

Great location clean and friendly staff

Reviewed on Jan 19, 2026

John Yancey Oceanfront Inn

Save 100% on your flight

$491

per person

Apr 11 - Apr 18

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9/10 Wonderful! (1,793 reviews)

Rooms were very clean we were impressed. Staff was very friendly and helpful. Slow time of the year to visit but the hotel is very near some of the best restaurants. Kill Devil Grill right across the street was outstanding.

Reviewed on Jan 20, 2026

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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

Chesapeake Hotel Deals

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

Fully refundableReserve now, pay when you stay

$75 nightly

$88 total

Feb 1 - Feb 2

Total with taxes and fees

7.8/10 Good! (1,003 reviews)

Clean room, great staff, nice location

Reviewed on Jan 15, 2026

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

Fully refundableReserve now, pay when you stay

$78 nightly

$91 total

Feb 8 - Feb 9

Total with taxes and fees

8.6/10 Excellent! (1,002 reviews)

The rooms are always clean. I wonder why I can never get an early check in though. If everyone checks out at 11 how is not a single room available till 300.

Reviewed on Jan 17, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG

721 Conference Center Drive Chesapeake VA

Fully refundable

$83 nightly

$97 total

Jan 25 - Jan 26

Total with taxes and fees

8.6/10 Excellent! (1,002 reviews)

Clean rooms, nice stuff

Reviewed on Jan 15, 2026

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.

Things to do in and around Chesapeake

Chesapeake, Virginia, offers a delightful mix of activities for families, couples, and outdoor enthusiasts. Enjoy leisurely strolls along the scenic boardwalk, explore vibrant shopping centers, and indulge in nature walks. Discover friendly attractions, relax at picturesque gazebos, and take in beautiful sightseeing experiences that showcase the area's charm. Whether you're looking for adventure or relaxation, Chesapeake has something for everyone to enjoy.

Shopping

In Chesapeake, you can enjoy shopping at Greenbrier Mall, which offers a variety of stores and entertainment. Chesapeake Square Mall features a similar vibe, perfect for family outings. If you're up for a drive, check out Cedar Lakes Retail Center for more shopping options in a lively atmosphere.

Recreation

Experience the vibrant atmosphere at Harbor Park, where you can catch an exciting game and soak in the energizing sports vibes. For a night of live music, head to The NorVa, a fantastic venue filled with entertainment energy. Enjoy relaxation and nature at Oak Grove Lake Park, perfect for unwinding.

Adventure

Experience the thrill of arcade games at Jillian's Billiards in Chesapeake, where family fun meets adventure. Enjoy outdoor activities and camping at Northwest River Park and Campground, perfect for nature lovers. For tennis enthusiasts, Folkes - Stevens Indoor Tennis Center offers exciting adventure activities a short drive away.

Nightlife

Chesapeake's nightlife features lively spots like Greenbrier Mall’s bars, the trendy downtown scene, and local breweries. Enjoy live music at venues like The Norva in nearby Norfolk or dance at clubs around the area, creating an energetic atmosphere for a memorable night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chesapeake

Chesapeake, Virginia, is an ideal destination for family, outdoor, and romantic vacations. Visitors can explore a variety of attractions including urban parks, a maritime museum, and a historic college university. The area offers rich cultural experiences and beautiful outdoor settings, particularly around the stunning Chesapeake Bay, making it perfect for travelers seeking both adventure and relaxation.

Norfolk State University: A historic institution deeply rooted in culture, Norfolk State University offers visitors a glimpse into its rich heritage and vibrant student life. The campus features beautiful architecture and engaging events that celebrate diversity and academic excellence.
Norfolk Scope: This lively arena serves as a hub for family-friendly entertainment, hosting concerts, sports events, and community gatherings. Its energetic atmosphere and diverse programming make it a perfect spot for a fun outing with family and friends.
Regent University: A modern campus that embodies a city vibe, Regent University blends academic rigor with a welcoming community. Visitors can explore its stunning facilities and enjoy the tranquil surroundings, making it a great place for reflection and inspiration.

Best time to go to Chesapeake

The best time to visit Chesapeake is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	41.0°F (5.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	49.3°F (9.6°C)	Light Rain	Mostly Sunny	Average	Average
April	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
June	75.2°F (24.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	79.7°F (26.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Average	Average
October	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Chesapeake

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chesapeake.
Consider traveling to Chesapeake during the low season (December to February) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Language

English

Currency

U.S dollars

Closest Airport

Norfolk Intl. Airport (ORF)

Population

235,400

Max Temp Winter

50ºF

Max Temp Summer

85ºF