Chesapeake Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Chesapeake

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

Things to do in and around Chesapeake

Chesapeake, Virginia, offers a delightful array of activities suitable for families, couples, and outdoor enthusiasts alike. Explore the scenic boardwalk, indulge in retail therapy at shopping centres and malls, or enjoy the thrills of the Chesapeake Beach Water Park. With a variety of recreational and fun activities, including seasonal Halloween events, there’s something for everyone to enjoy in this charming city.

Shopping

In Chesapeake, visit Greenbrier Mall for a vibrant shopping experience with a blend of entertainment and family-friendly vibes. Las Gaviotas Shopping Center offers a city atmosphere with charming shops. If you’re up for a drive, Chesapeake Square Mall is another great option, featuring a mix of businesses and leisure activities.

Recreation

The Norva Theatre offers a captivating blend of romance and culture with its diverse entertainment options, perfect for unwinding. Meanwhile, Commodore Theatre provides a charming cinematic experience, ideal for family outings or a romantic evening. Enjoy a vibrant atmosphere at The NorVa, where music concerts elevate your spirits.

Adventure

Experience the great outdoors at Northwest River Park and Campground, perfect for family adventures. For indoor fun, visit Jillian's Billiards, an exciting arcadeAdventureZone. If you're keen on sports, head to Tidewater Tennis Center, located 12.9km away, for thrilling tennis activities.

Nightlife

In Chesapeake, Virginia, enjoy a vibrant nightlife scene at venues like the Greenbrier area, featuring lively bars and restaurants. Experience live music and dancing at local hotspots, while the nearby waterfront offers a scenic backdrop for relaxed evenings with friends. Perfect 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 in and around Chesapeake

Chesapeake is an excellent destination for family, outdoor, and romantic getaways. Explore urban parks, maritime museums, and entertainment arenas, while enjoying beautiful beaches and the scenic Chesapeake City Park. Don't miss out on Chesapeake Beach and nearby attractions, as well as a visit to Chesapeake Square Mall for shopping. This vibrant area offers a delightful blend of culture and outdoor experiences for every traveller.

  • USS Wisconsin BB-64: Explore the historic USS Wisconsin, a magnificent battleship that now serves as a maritime museum. Located only 8.0km from Chesapeake, visitors can immerse themselves in naval history, discovering exhibits that highlight the ship's storied past and its role in American maritime culture.
  • Chesapeake Central Library: Situated within Chesapeake, this library offers a welcoming atmosphere for families and culture enthusiasts alike. With a wide range of resources, community events, and a serene reading environment, it’s a perfect spot to relax and engage with the local community.
  • Pagoda and Oriental Garden: Just 9.7km from Chesapeake, this private garden boasts beautiful landscapes and historical significance. Stroll through its tranquil paths, admire the stunning pagoda, and enjoy the serene ambiance that reflects rich cultural heritage.

Best time to go to Chesapeake

The best time to visit Chesapeake can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chesapeake falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chesapeake falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January41.0°F (5.0°C)Light RainMostly SunnyAverageSlightly Low
February43.7°F (6.5°C)Light RainMostly SunnyAverageSlightly Low
March49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
April58.6°F (14.8°C)Light RainMostly SunnySlightly HighAverage
May67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
June75.2°F (24.0°C)Light RainMostly SunnySlightly HighSlightly High
July79.7°F (26.5°C)Light RainMostly SunnySlightly HighSlightly High
August78.4°F (25.8°C)Light RainMostly SunnyAverageSlightly High
September73.6°F (23.1°C)Light RainMostly SunnyAverageAverage
October64.0°F (17.8°C)Light RainMostly SunnySlightly LowAverage
November52.9°F (11.6°C)Light RainMostly SunnySlightly LowAverage
December46.4°F (8.0°C)Light RainMostly SunnySlightly LowSlightly 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 during the off-peak season (typically December to February) for more affordable package holidays to Chesapeake.
  • 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.

Top hotels in Chesapeake

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 €65 per night from 8 Jul to 9 Jul
€65
8 Jul - 9 Jul
includes taxes & fees
7.2/10 Good! (872 reviews)
"Table was dirty, I brought a pack of washcloths with me and used one to clean the table. It came out red, like if juice was spilled and never cleaned. I started cleaning the rest of the rooms surfaces and it wasn’t too bad. I dropped the rag on the floor and wiped a small area by stepping on it. ..."

Reviewed on 5 Jul 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 €142 per night from 14 Jul to 15 Jul
€142
14 Jul - 15 Jul
includes taxes & fees
7.4/10 Good! (21 reviews)
"Todo"

Reviewed on 6 Jul 2026

Hyatt Studios Chesapeake
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is €133 per night from 26 Jul to 27 Jul
€133
26 Jul - 27 Jul
includes taxes & fees
7.8/10 Good! (1,104 reviews)
"Pool was open, water was super cold. Breakfast was yummy."

Reviewed on 5 Jul 2026

Wingate by Wyndham 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.

Stay near popular Chesapeake attractions

What to do in Chesapeake

Frequently asked questions

How much does a Chesapeake holiday package cost?
You'll find cheap prices on Expedia for your Chesapeake escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake holiday package, consider planning a trip in January, February and November. You'll generally find better prices on accommodation and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Chesapeake?
Chesapeake holidays can be as short or long as you like, but to get a real feel for this destination, we reckon 2 days is about right. With this timeframe, you can fit in top sights like Chesapeake City Park and Oak Grove Lake Park along with lesser-known spots. Don't forget to visit neighbourhoods such as Greenbrier East and Greenbrier West either. If you're smart with your time, you can even take a day trip from Chesapeake too.
Is it worth booking a holiday package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake holiday has something for everyone. Be sure to check out major sights like Portlock Galleries at SoNo and Oak Grove Lake Park, and consider renting a car for day trips to experience even more.
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 holiday as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customised holiday 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 holiday 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 the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Chesapeake.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Chesapeake. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Chesapeake holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.