Chesapeake Holidays

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Your Chesapeake Holiday

Lock in a Chesapeake holiday 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 holiday is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

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, is perfect for family, outdoor, and romantic getaways. Visitors can enjoy a scenic boardwalk, vibrant shopping centres, and a variety of fun tours. Outdoor activities abound, alongside Gulf Coast trips and holiday events, making it an ideal destination for all types of travellers seeking adventure and relaxation.

Shopping

In Chesapeake, you can visit Greenbrier Mall for a vibrant shopping experience with various shops and entertainment options. Cedar Lakes Retail Center offers a mix of family-friendly stores. If you're up for a drive, check out Chesapeake Square Mall for more shopping and entertainment.

Recreation

Harbor Park, a vibrant sports stadium, offers an energetic atmosphere perfect for enjoying live sports. Commodore Theatre provides a charming cinematic experience with family-friendly films and romantic options. The NorVa, an exciting music venue, showcases diverse performances, ensuring an entertaining evening filled with great tunes.

Adventure

Experience the great outdoors at Northwest River Park and Campground with camping and nature trails, embrace family fun at Jillian's Billiards arcadeAdventureZone, or indulge in some indoor sports at Folkes - Stevens Indoor Tennis Center, located 12.9km from Chesapeake, perfect for an adventurous day out.

Nightlife

Chesapeake's nightlife offers a vibrant mix of bars and live music. Visit the Greenbrier Bar and Grill for delightful cocktails, or enjoy local bands at the Chesapeake Music Hall. For a relaxed atmosphere, the Craft Beer Cellar is perfect for sampling unique brews with friends.

*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, Virginia, offers a delightful blend of family-friendly activities, outdoor adventures, and romantic getaways. Visitors can explore urban parks, maritime museums, and historic college campuses, catering to those seeking culture and nature. With nearby attractions, beautiful beaches, and noteworthy sites, Chesapeake promises an enriching experience for all types of travellers looking to immerse themselves in local charm.

  • USS Wisconsin BB-64: This remarkable maritime museum offers a unique glimpse into naval history aboard one of the last battleships commissioned by the U.S. Navy. You can explore the ship’s decks, admire its impressive armaments, and gain insight into life at sea during wartime, all while soaking up the cultural vibes it exudes.
  • Lake Drummond: Nestled within Chesapeake, Lake Drummond is a picturesque spot perfect for outdoor enthusiasts. Enjoy scenic walks along the shoreline, indulge in romantic picnics, or simply bask in the tranquil beauty of nature, making it an ideal retreat for relaxation and adventure.
  • Pagoda and Oriental Garden: A hidden gem, this private garden enchants visitors with its historical charm and serene environment. Stroll through beautifully landscaped grounds adorned with traditional Asian architecture, offering a peaceful escape and a chance to reflect on the rich history it represents.

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.

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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

Top hotels in Chesapeake

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is £72 per night from 29 Mar to 30 Mar
£72
29 Mar - 30 Mar
includes taxes & fees
8/10 Very Good! (1,006 reviews)
The room needed more cleaning, breakfast was great!

Reviewed on 22 Mar 2026

Wingate by Wyndham Chesapeake
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundable
The price is £84 per night from 19 Apr to 20 Apr
£84
19 Apr - 20 Apr
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
Yes

Reviewed on 21 Mar 2026

Comfort Suites Chesapeake - Norfolk
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is £87 per night from 29 Mar to 30 Mar
£87
29 Mar - 30 Mar
includes taxes & fees
8.6/10 Excellent! (404 reviews)
Clean room,

Reviewed on 20 Mar 2026

TRU by Hilton Chesapeake, VA
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.

Popular places to visit

What to do in Chesapeake

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.