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

Greenbrier East

If you're spending some time in Greenbrier East, Greenbrier Mall and Jillian's Billiards are top sights worth seeing.

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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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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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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 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

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

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
₹9,109
₹11,376 total
31 Aug - 1 Sept
includes taxes & fees
Wyndham Virginia Beach Oceanfront
Ocean Resort

Ocean Resort

Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
₹7,764
₹10,442 total
20 Sept - 21 Sept
includes taxes & fees
Ocean Resort
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

4453 Bonney Rd Virginia Beach VA
Fully refundable
₹8,906
₹10,433 total
7 Sept - 8 Sept
includes taxes & fees
Crowne Plaza Virginia Beach Town Center by IHG
See all 3,495 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 CVS store with a large archway and a red star logo.

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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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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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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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.