Why should I book my Chesapeake holiday with Expedia?

With top-value flights, car hire and accommodation options all in one convenient place, Expedia makes arranging your Chesapeake break simple. Plus, we can help you bundle your bookings into a package holiday so you can get even more savings. Pick from awesome stays, add your flights and/or a hire car (and maybe also some exciting tours and activities!) and get unbeatable prices. Want to change your plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, check out our Customer Service Portal link .

When is the best time of year to holiday in Chesapeake?

If you'd like to experience the vibe of Chesapeake in peak season, plan your getaway for March, May and August. December, January and February are generally the quietest months of the year. To get an idea of the type of weather to expect, the average daytime temperature in January, the coolest month in Chesapeake, is 4ºC. The warmest month here is July, when temperatures average 26ºC.

What are the top hotels for my holiday in Chesapeake?

If you're thinking of staying in the Greenbrier East neighbourhood, Hyatt Place Chesapeake and Homewood Suites by Hilton Chesapeake-Greenbrier are terrific options. Western Branch North is also a favourite Chesapeake area. We recommend Comfort Inn & Suites Chesapeake - Portsmouth or SpringHill Suites by Marriott Chesapeake Greenbrier if you choose this part of the city.

How do I get a cheap holiday to Chesapeake?

Bundle your flights and hotels with Expedia to save on your next big adventure. With more than 400 airlines and 321,000 hotels across the world, your Chesapeake holiday can be tailored exactly to suit your travel style. With all that extra money, why not include some awesome activities and tours? It's an easy way to unlock even more discounts. That dream holiday to Chesapeake is closer than you thought! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.

What should I do on my Chesapeake holiday?

With must-see tourist attractions such as Greenbrier Mall and Chesapeake Square Mall , a holiday in Chesapeake is filled with exciting things to see and do. Chesapeake Conference Centre and Chesapeake Regional Medical Centre are two other sights worth discovering.

What is the best area to stay in when on holiday in Chesapeake?

If you plan to visit Greenbrier Mall, maximise your time sightseeing and find a place to stay close by. It's one of the most popular attractions in Chesapeake.

Do I need a visa for my Chesapeake holiday?

Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for tourism or work, will determine if you need a visa for Chesapeake. Also be sure that your passport is up to date and has a minimum of six months validity remaining beyond your intended return date. Do all your travel planning well ahead of time to avoid any nasty last-minute surprises.

What should I wear on my Chesapeake holiday?

First, consider the activities planned during your holiday in Chesapeake and choose versatile pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, look up style blogs or relevant social media accounts. Pack your luggage with confidence by monitoring the weather forecast in Chesapeake. July brings the warmest temperatures, with daily averages of 26ºC, while January days average 4ºC, making it the coolest time of year.

What does an Expedia Chesapeake holiday include?

Flights, car hires and hotels, or any combination of the three — the choice is yours. Whether you're headed to Chesapeake with the whole family or enjoying a solo break, there's a bundle to suit every style and budget. Once you've made your booking, why not add on one or two tours and experiences? Private holiday homes and apartments are a couple of the most highly sought-after property types in Chesapeake. Whatever your group size or holiday style, you can rely on Expedia for the freedom and flexibility to customise your next big adventure.

Does Expedia offer Book Now, Pay Later Chesapeake holidays?

Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options: Pay monthly holidays : Escape on that dream holiday sooner with Klarna's convenient payment plans. If paying across multiple instalments sounds right for you, choose this option at checkout. No-deposit holidays : Pressing the "book now" button is easier with this payment option. With no deposit required for your escape, you can Book Now, Pay Later and start working on your travel plans.

Can I choose my airline with a Chesapeake Expedia holiday?

Yes — that's one of the best things about an Expedia holiday package. You're in control. We have more than 400 airline partners around the world, so you have lots of choice when putting together your Chesapeake adventure.

Chesapeake Holidays 2026 from £933

Top Chesapeake Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.

The Atrium Resort, Virginia Beach by Vacatia

Northeast Virginia Beach

£933

per person

28 Aug - 3 Sept

found 7 hours ago

Return direct flight included

London (LON) to Norfolk (ORF)

8.2/10 Very good! (1,530 reviews)

The photos online did not actually reflect how nice the room amenities were. I didn't expect a fully stocked kitchenette complete with cookware, dishes, and silverware. I was traveling with my children, so these little things helped. There's ample parking and the location is very close to the beach. The staff was very helpful and I would definitely recommend this place as an option if you're budget conscious.

Reviewed on 8 Jul 2026

The Colony at Virginia Beach

Northeast Virginia Beach

£1,208

per person

28 Aug - 3 Sept

found 7 hours ago

Return direct flight included

London (LON) to Norfolk (ORF)

9.4/10 Exceptional! (23 reviews)

Property was clean, and staff friendly.

Reviewed on 6 Jul 2026

The Ocean Key Virginia Beach Resort

Northeast Virginia Beach

£958

per person

28 Aug - 3 Sept

found 7 hours ago

Return direct flight included

London (LON) to Norfolk (ORF)

7.6/10 Good! (1,562 reviews)

My 2nd favorite place to stay at VA BEACH

Reviewed on 7 Jul 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG

Northeast Virginia Beach

£1,011

per person

28 Aug - 3 Sept

found 7 hours ago

Return direct flight included

London (LON) to Norfolk (ORF)

8/10 Very good! (1,403 reviews)

Location was great. Rooms were spacious. No housekeeping service . Elevators were terrible. Pool area was poorly maintained with used towels not being picked up. Parking was not great

Reviewed on 8 Jul 2026

Hilton Vacation Club Oceanaire Virginia Beach

Northeast Virginia Beach

£1,345

per person

28 Aug - 3 Sept

found 7 hours ago

Return direct flight included

London (LON) to Norfolk (ORF)

8.4/10 Very good! (1,138 reviews)

Our suite had so much space for our 4 family stay! Everyone was comfortable. Living room and kitchen were a must. The bathroom was a little outdated in the dbl room, but other than that no complaints. My kids loved all the pools and the direct beach access. Close to restaurants. Great stay

Reviewed on 7 Jul 2026

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, is perfect for family, outdoor, and romantic getaways. Visitors can enjoy a scenic boardwalk, vibrant shopping centres, and a variety of fun tours. Outdoor activities abound, alongside Gulf Coast trips and holiday events, making it an ideal destination for all types of travellers seeking adventure and relaxation.

Shopping

In Chesapeake, you can visit Greenbrier Mall for a vibrant shopping experience with various shops and entertainment options. Cedar Lakes Retail Center offers a mix of family-friendly stores. If you're up for a drive, check out Chesapeake Square Mall for more shopping and entertainment.

Recreation

Harbor Park, a vibrant sports stadium, offers an energetic atmosphere perfect for enjoying live sports. Commodore Theatre provides a charming cinematic experience with family-friendly films and romantic options. The NorVa, an exciting music venue, showcases diverse performances, ensuring an entertaining evening filled with great tunes.

Adventure

Experience the great outdoors at Northwest River Park and Campground with camping and nature trails, embrace family fun at Jillian's Billiards arcadeAdventureZone, or indulge in some indoor sports at Folkes - Stevens Indoor Tennis Center, located 12.9km from Chesapeake, perfect for an adventurous day out.

Nightlife

Chesapeake's nightlife offers a vibrant mix of bars and live music. Visit the Greenbrier Bar and Grill for delightful cocktails, or enjoy local bands at the Chesapeake Music Hall. For a relaxed atmosphere, the Craft Beer Cellar is perfect for sampling unique brews with friends.

*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, offers a delightful blend of family-friendly activities, outdoor adventures, and romantic getaways. Visitors can explore urban parks, maritime museums, and historic college campuses, catering to those seeking culture and nature. With nearby attractions, beautiful beaches, and noteworthy sites, Chesapeake promises an enriching experience for all types of travellers looking to immerse themselves in local charm.

USS Wisconsin BB-64: This remarkable maritime museum offers a unique glimpse into naval history aboard one of the last battleships commissioned by the U.S. Navy. You can explore the ship’s decks, admire its impressive armaments, and gain insight into life at sea during wartime, all while soaking up the cultural vibes it exudes.
Lake Drummond: Nestled within Chesapeake, Lake Drummond is a picturesque spot perfect for outdoor enthusiasts. Enjoy scenic walks along the shoreline, indulge in romantic picnics, or simply bask in the tranquil beauty of nature, making it an ideal retreat for relaxation and adventure.
Pagoda and Oriental Garden: A hidden gem, this private garden enchants visitors with its historical charm and serene environment. Stroll through beautifully landscaped grounds adorned with traditional Asian architecture, offering a peaceful escape and a chance to reflect on the rich history it represents.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	41.0°F (5.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	49.3°F (9.6°C)	Light Rain	Mostly Sunny	Average	Average
April	58.6°F (14.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
June	75.2°F (24.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	79.7°F (26.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	73.6°F (23.1°C)	Light Rain	Mostly Sunny	Average	Average
October	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	52.9°F (11.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	46.4°F (8.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly 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 to Chesapeake during the low season (December to February) for more affordable options.
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.

Language	English
Currency	U.S dollars
Closest Airport	Norfolk Intl. Airport (ORF)
Population	235,400
Max Temp Winter	10ºC
Max Temp Summer	29ºC
Top Sights	Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

Language

English

Currency

U.S dollars

Closest Airport

Norfolk Intl. Airport (ORF)

Population

235,400

Max Temp Winter

10ºC

Max Temp Summer

29ºC

Top Sights

Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

Top hotels in Chesapeake

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

Fully refundableReserve now, pay when you stay

£54

23 Jul - 24 Jul

includes taxes & fees

7.2/10 Good! (876 reviews)

"I love the staff they are great only problem I have is they have no soda machines no coffee in the office or in the rooms it's kind of inconvenient"

Reviewed on 9 Jul 2026

Hyatt Studios Chesapeake

101 Volvo Parkway Chesapeake VA

Fully refundableReserve now, pay when you stay

£122

26 Jul - 27 Jul

includes taxes & fees

7.8/10 Good! (24 reviews)

"Check in July 2nd and Departed July 6th newer hotel everything was still fairly new spotless up to date dishwasher refrigerator stove top electric and microwave oven good size flat screen television and comfortable bed and couch nice clean also bed couch at that walk in shower space decent I am glad ..."

Reviewed on 8 Jul 2026

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

Fully refundableReserve now, pay when you stay

£102

9 Aug - 10 Aug

includes taxes & fees

9.6/10 Exceptional! (126 reviews)

"I stayed for five days and this was my first time at the property and I have no complaints the staff was excellent especially Chanel l don't think that's how you spell her name but she works 3 to 11 and she was very nice to me the rooms have washer and dryer I really loved that the patio area was ..."

Reviewed on 6 Jul 2026

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