Chesapeake Holidays

Photo by Kaylee Spinhirn
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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

Things to do in and around Chesapeake

Chesapeake is perfect for family, outdoor, and romantic getaways, offering a variety of activities such as exploring the scenic boardwalk and indulging in shopping at local centres and malls. Visitors can enjoy outdoor experiences, partake in fun activities, and attend Halloween events. The Chesapeake Beach Water Park is a must-visit for a splash of excitement. Overall, Chesapeake promises a delightful mix of adventure and relaxation for all its guests.

Shopping

For a delightful shopping experience in Chesapeake, visit Greenbrier Mall, Las Gaviotas Shopping Center, and Chesapeake Square Mall, all offering vibrant city and family vibes. If you're up for a drive, explore additional shopping options beyond the city limits for even more variety.

Recreation

Experience the vibrant entertainment at The NorVa, just 9.7km from Chesapeake, where live music energises the atmosphere. Alternatively, find solace at Oak Grove Lake Park, a local gem for wellness and relaxation, offering serene landscapes right within the city.

Adventure

Northwest River Park and Campground offers a delightful outdoor experience with family-friendly camping amidst nature. For some indoor excitement, visit Jillian's Billiards, where you can enjoy arcade games. If you're keen on sports, the Tidewater Tennis Center, located 12.9km away, provides thrilling tennis activities.

Nightlife

Chesapeake's nightlife offers a blend of lively bars and intimate venues. For a vibrant atmosphere, visit the Greenbrier area where you can enjoy craft cocktails at local bars. Alternatively, the downtown scene features cozy pubs perfect for a relaxed evening with friends.

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

Find the best attractions near Chesapeake

Chesapeake, Virginia, offers an ideal getaway for families, couples, and outdoor enthusiasts alike. Visitors can explore diverse attractions such as urban parks, maritime museums, and entertainment arenas. Noteworthy sites include Chesapeake Square Mall, Chesapeake City Park, and various local attractions, ensuring a rich experience steeped in culture and outdoor adventure. Whether you’re attending Veterans Day events or simply enjoying the scenery, Chesapeake promises a memorable holiday for all.

  • USS Wisconsin BB-64: Experience the grandeur of this historic battleship, now a maritime museum, where you can explore its decks, learn about naval history, and appreciate the craftsmanship that went into its construction. The cultural vibes are palpable as you walk through the ship's storied past, making it a must-visit.
  • Hampton Roads Naval Museum: Delve into the rich military heritage of the region at this engaging museum. Exhibits highlight the significance of naval operations and the impact they’ve had on American history, all set within a vibrant cultural context that brings the past to life.
  • Douglas MacArthur Memorial: Discover the legacy of General Douglas MacArthur at this poignant memorial and museum. Featuring exhibits on MacArthur's life and career, visitors can immerse themselves in history while appreciating the cultural significance of his contributions to military strategy and leadership.

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

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

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is S$119 per night from 8 Feb to 9 Feb
S$119
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Friendly staff and clean room makes this hotel a great place to stay.

Reviewed on 23 Jan, 2026

Comfort Suites Chesapeake - Norfolk
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 S$112 per night from 8 Feb to 9 Feb
S$112
8 Feb - 9 Feb
includes taxes & fees
7.8/10 Good! (1,006 reviews)
Great Stay

Reviewed on 26 Jan, 2026

Wingate by Wyndham Chesapeake
Holiday Inn Express Chesapeake - Norfolk by IHG

Holiday Inn Express Chesapeake - Norfolk by IHG

2.5 out of 5
721 Conference Center Drive Chesapeake VA
Fully refundable
The price is S$123 per night from 8 Feb to 9 Feb
S$123
8 Feb - 9 Feb
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Staff are always awesome!!!! I stay here alot

Reviewed on 24 Jan, 2026

Holiday Inn Express Chesapeake - Norfolk by IHG
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.

What to do in Chesapeake

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