Chesapeake Holidays

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Photo by Kaylee Spinhirn

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Your Chesapeake Holiday

Pick a Chesapeake holiday package and you can prioritize what matters — enjoying yourself. No more planning hassles, just more free time to immerse yourself in the delights of this fascinating city, such as its rich history and family-friendly attractions. Eager to get out and explore? Greenbrier Mall, Chesapeake City Park and Chesapeake City Hall are just three of the most popular places to visit during a trip to Chesapeake. No matter your travel plans or the size of your budget, organising your ultimate tailored Chesapeake holiday is simple with Expedia.

Our guide on where to stay in Chesapeake

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

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
Jillians Billiards, Portlock Galleries at SoNo and Chesapeake City Park

Our pick of the best Chesapeake Hotel Deals

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 AU$153 per night from 7 Aug to 8 Aug
AU$153
7 Aug - 8 Aug
includes taxes & fees
7/10 Good! (1,003 reviews)
"It was affordable and within a good range of everything needed. The staff was welcoming."

Reviewed on 28 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 AU$97 per night from 6 Aug to 7 Aug
AU$97
6 Aug - 7 Aug
includes taxes & fees
6.4/10 (484 reviews)
"Great"

Reviewed on 31 Jul. 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 1 Sept to 2 Sept
AU$175
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (1,584 reviews)
"Loved it!"

Reviewed on 31 Jul. 2025

Wyndham Virginia Beach Oceanfront
See all 3,429 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Chesapeake

Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

AU$62
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
View of Spirit of Norfolk

Spirit of Norfolk Signature Brunch Cruise

AU$170
per adult
86% of travellers recommend
Spirit of Norfolk Signature Brunch Cruise
Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

AU$191
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.