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
A wooden pier extending into a calm lake, surrounded by dense trees.

Greenbrier

5 out of top 10 points of interest in this area

While visiting Greenbrier, you might make a stop by sights like Greenbrier Mall and Chesapeake Arboretum.

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Deep Creek South

1 out of top 10 points of interest in this area

While visiting Deep Creek South, you might make a stop by sights like The Crossings at Deep Creek Shopping Center and Deep Creek Park.

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A sunset over a calm river with industrial structures and a large bridge.

Greenbrier East

Greenbrier East might not have many top sights, but Greenbrier Mall and Chesapeake Conference Center are two attractions nearby that you can check out.

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A person standing on a boat deck facing a foggy landscape with a ship in the distance and the sun setting on the horizon.

Greenbrier West

While visiting Greenbrier West, you might make a stop by sights like Chesapeake Arboretum and Bowlero Chesapeake.

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A coastal cityscape with a large ship docked at a port, modern buildings, and a river.

South Norfolk

If you're looking for some top things to see and do in South Norfolk and surrounding area, you can visit Chesapeake Conference Center and Greenbrier Mall.

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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

1550 Crossways Blvd Chesapeake VA
Fully refundable
S$140
4 Oct - 5 Oct
includes taxes & fees
8.8/10 Excellent! (1,091 reviews)
"Well kept clean hotel, not so quiet yiu can here other room. But overall nice place, would stay again"

Reviewed on 10 Sept, 2026

Comfort Suites Chesapeake - Norfolk
Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
S$212
14 Sept - 15 Sept
includes taxes & fees
Hyatt Studios Chesapeake
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
S$140
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (205 reviews)
"Everything was nice beds were a little too firm which made it a little uncomfortable but overall the stay was wonderful"

Reviewed on 13 Sept, 2026

YourSpace Hotels Chesapeake
See all 3,512 properties in 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

A building with a large arched entrance, surrounded by trees and a parking lot.

Greenbrier Mall

8.4/10 (837 reviews)
This regional shopping centre features over 100 stores and eateries, plus a Cinema Café for dining during films. Families enjoy the supervised soft play area and convenient amenities while shopping.
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A building with a clock tower, surrounded by pink flowers and greenery.

Chesapeake Square Mall

8.2/10 (429 reviews)
Chesapeake Square Mall blends shopping with entertainment at its 12-screen Cinemark XD theatre. Visit weekday mornings for a relaxed experience at this regional retail centre undergoing a $30 million revitalisation.
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A modern building with a curved glass facade and a sign reading "Chesapeake Conference Center."

Chesapeake Conference Center

7.8/10 (169 reviews)
This versatile 39,000-square-foot venue hosts elegant weddings to professional conferences in Chesapeake, Virginia. The on-site catering team delivers customised dining experiences with free Wi-Fi and parking.
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A wooden bridge over a calm river surrounded by dense forest.

Chesapeake City Park

8.2/10 (180 reviews)
This sprawling 90-acre recreational haven hosts Chesapeake's signature events like the Jubilee and Symphony Under the Stars. Families enjoy the Fun Forest Playground and peaceful walking trails.
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A solitary tree in a swampy area with water around its base.

Lake Drummond

7.8/10 (12 reviews)
Lake Drummond, one of only two natural freshwater lakes in Virginia, sits at the heart of Great Dismal Swamp. Paddle through tea-colored waters while spotting black bears and rare birds in this serene ecosystem.
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A wooden pier extending into a calm lake, surrounded by dense trees.
Photo by Kaylee Spinhirn

Oak Grove Lake Park

7.6/10 (39 reviews)
Encircling a serene 65-acre lake, this park's 1.5-mile trail offers picturesque views and abundant wildlife. Enjoy fishing from accessible platforms or relax at shaded picnic areas overlooking the water.
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Dismal Swamp Canal

The oldest hand-dug waterway still operating in America, this historic canal connects the Chesapeake Bay to Albemarle Sound. Paddle through its serene waters while spotting wildlife and exploring its history.
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Chesapeake Arboretum

7.6/10 (76 reviews)
Enjoy an outing to Chesapeake Arboretum during your stay in Chesapeake. Amble around the area's beautiful beaches or attend a sporting event.
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What to do in Chesapeake

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

S$54
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

S$115
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

S$30
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
See all activities 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.

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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.