Chesapeake Vacations

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    Save up to SAR 390 when you book a flight and hotel together*
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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
Greenbrier Mall

Greenbrier East

1 out of top 10 points of interest in this area
4/5(438 area reviews)

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

Find hotels in Greenbrier East

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

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 SAR 198 per night from Sep 4 to Sep 5
SAR 198
SAR 235 total
4 Sep - 5 Sep
includes taxes & fees
6.6/10 (514 reviews)
"The room was clean and the bed was excellent. The blanket was more like a sheet than a blanket. But overall it was a peaceful stay."

Reviewed on 21 August 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
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
Fully refundable
The price is SAR 479 per night from Sep 1 to Sep 2
SAR 479
SAR 558 total
1 Sep - 2 Sep
includes taxes & fees
8.2/10 Very Good! (2,256 reviews)
"Everything was amazing. Just the pool needs more attention. Is not perfect clean. Thank you"

Reviewed on 19 August 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is SAR 316 per night from Sep 21 to Sep 22
SAR 316
SAR 371 total
21 Sep - 22 Sep
includes taxes & fees
8.2/10 Very Good! (1,080 reviews)
"I didn't care that you couldn't park right on this property. The pool was cloudy for most of our stay but the hotel was clean"

Reviewed on 21 August 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
See all 3,420 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.

Discover the most popular places to visit in Chesapeake

Greenbrier Mall

Greenbrier Mall

You can browse for the perfect souvenirs 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 find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater 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 great live music and acclaimed theater scene.

Chesapeake Conference Center

Frequently asked questions

How much does a Chesapeake vacation 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 vacation to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake vacation package, consider planning a trip in January, February and November. You'll generally find better prices on accommodations and flights during these months — perfect for travelers wishing to save money.
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 vacation as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customized vacation 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 vacation 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, favorite 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 vacation package that brings all your bookings together.