Chesapeake Trip

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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

Shopping

Chesapeake offers a delightful shopping experience at Greenbrier Mall and Chesapeake Square Mall, both featuring a mix of entertainment and family-friendly vibes. If you're up for a drive, consider visiting Las Gaviotas Shopping Center for a unique blend of city and business atmosphere.

Recreation

Experience the vibrant atmosphere at Harbor Park, where you can immerse yourself in exciting sports events. Enjoy a cinematic outing at Commodore Theatre, perfect for family entertainment and romantic evenings. For more sports thrills, head to Frank D Lawrence Stadium, where the energy of the game awaits.

Adventure

Experience thrilling fun at Jillian's Billiards arcadeAdventureZone, where family-friendly excitement awaits. Embrace the outdoors at Northwest River Park and Campground, perfect for camping adventures. For a different challenge, visit Tidewater Tennis Center, located 12.9km from Chesapeake, and enjoy an energetic game of tennis.

Nightlife

In Chesapeake, Virginia, enjoy a vibrant nightlife at venues like the Greenbrier Mall, featuring bars and restaurants. Discover live music at local pubs and unwind at stylish lounges, where friendly atmospheres and delightful cocktails create memorable evenings in this charming coastal city.

*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, is an ideal destination for family, outdoor, and romantic getaways. Visitors can explore urban parks, maritime museums, and entertainment arenas while enjoying the local culture and nature. Highlights include the Chesapeake City Park, the beautiful Chesapeake Arboretum, and stunning nearby beaches. Additionally, special events like Veterans Day provide unique experiences, ensuring a memorable trip for all types of travellers.

  • Norfolk Scope: Located 9.7km from Chesapeake, Norfolk Scope is an energetic arena that hosts a variety of events, from concerts to sports. Its lively atmosphere and family-friendly vibe make it a popular gathering place where you can enjoy thrilling performances and unforgettable moments with loved ones.
  • USS Wisconsin BB-64: Situated 8.0km away, this maritime museum offers a unique glimpse into naval history. Visitors can explore the battleship’s impressive decks, learn about its storied past, and immerse themselves in the rich culture of maritime heritage that this iconic vessel represents.
  • Chesapeake Conference Center: Nestled within Chesapeake, this venue caters to a variety of business events and conferences. Its modern facilities and professional ambiance provide the perfect setting for networking and collaboration, ensuring a productive experience for all attendees.

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 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 ₹8,491 per night from 19 Apr to 20 Apr
₹8,491
₹9,951 total
19 Apr - 20 Apr
includes taxes & fees
8/10 Very Good! (1,003 reviews)
The jets in the hot tub werent workonh

Reviewed on 4 Apr 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 ₹9,829 per night from 19 Apr to 20 Apr
₹9,829
₹11,489 total
19 Apr - 20 Apr
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Staff were friendly, parking was easy and convenient. Breakfast was as good as you can expect for a place like this! My only complaint is our room wasn’t ready when we checked in (around 5pm) and we had to wait a little to get our keys. Wasn’t a long wait though.

Reviewed on 4 Apr 2026

Comfort Suites Chesapeake - Norfolk
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 ₹9,962 per night from 19 Apr to 20 Apr
₹9,962
₹11,642 total
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Everything was great as usual. Definitely my go to place to stay when Im in town. The staff aim to please. Amenities are always available when nedded. Parking was easy and breakfast was delicious..

Reviewed on 30 Mar 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.

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