Chesapeake Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kaylee Spinhirn

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 East

3.5/5(2 area reviews)

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

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Top hotels in Chesapeake

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
The price is 5.308.513 ₫ per night from 29 Jun to 30 Jun
5.308.513 ₫
6.157.051 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.2/10 Very Good! (1,014 reviews)
"Everything was good no complaints"

Reviewed on 22 Jun 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
The price is 5.352.686 ₫ per night from 2 Jul to 3 Jul
5.352.686 ₫
6.207.978 ₫ total
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (2,153 reviews)
"Rooms were clean. Hotel location was great. Staffs were polite. Breakfast is good, but could be better"

Reviewed on 21 Jun 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
8.6/10 Excellent! (3,174 reviews)
It was nice
"Its clean & cheap helpful staff no issues nice view"

Reviewed on 20 Jun 2025

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Schooner Inn
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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.

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.

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
Chesapeake Square Mall

Chesapeake Square Mall

You can search for that perfect souvenir at Chesapeake Square Mall during your visit to Chesapeake. Discover the top-notch restaurants and acclaimed theatre scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's acclaimed theatre scene and great live music.

Chesapeake Conference Center