Chesapeake Holidays

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Your Chesapeake Holiday

Lock in a Chesapeake holiday package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake holiday is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Default Image

Greenbrier

4 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.

Find hotels in Greenbrier

Chesapeake Essential Information

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

Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is £74 per night from 21 Jul to 22 Jul
£74
21 Jul - 22 Jul
includes taxes & fees
6.8/10 (1,003 reviews)
"Good stay, reasonably clean but room was very moist and there was mold in the bathroom."

Reviewed on 14 Jul 2025

Red Roof Inn Chesapeake Conference Center
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is £51 per night from 6 Aug to 7 Aug
£51
6 Aug - 7 Aug
includes taxes & fees
6.4/10 (446 reviews)
"It was great"

Reviewed on 14 Jul 2025

STUDIOS & SUITES 4 LESS 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 £95 per night from 27 Jul to 28 Jul
£95
27 Jul - 28 Jul
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"N/A"

Reviewed on 10 Jul 2025

Wingate by Wyndham Chesapeake
See all 3,444 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Greenbrier Mall

Greenbrier Mall

You can search for that perfect souvenir at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Greenbrier Mall

Lake Drummond

Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this family-friendly area or visit its top-notch restaurants.

Lake Drummond

What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

£102
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

£30
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

£24
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
See all activities in Chesapeake

Frequently asked questions

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.