Chesapeake Holidays

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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, 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

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 €81 per night from 26 Feb to 27 Feb
€81
26 Feb - 27 Feb
includes taxes & fees
8/10 Very Good! (1,007 reviews)
Everything was first-class!

Reviewed on 15 Feb 2026

Wingate by Wyndham 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 €80 per night from 1 Mar to 2 Mar
€80
1 Mar - 2 Mar
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
The stay was perfect. We requested bottom floor as we had a service dog. The room was beautiful and clean and service was awesome. Would definitely recommend and will be back. Thank you.

Reviewed on 14 Feb 2026

Comfort Suites Chesapeake - Norfolk
Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake

2.5 out of 5
1560 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is €89 per night from 5 Mar to 6 Mar
€89
5 Mar - 6 Mar
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Room was clean, staff very friendly. Bed was soft. Bathroom clean . Will return

Reviewed on 15 Feb 2026

Fairfield Inn and Suites By Marriott 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.

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What to do in Chesapeake

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