Chesapeake Vacations

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    Save up to SARĀ 5,400 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
A wooden pier extending into a calm lake, surrounded by dense trees.

Greenbrier

4 out of top 10 points of interest in this area

If you're spending some time in Greenbrier, Greenbrier Mall and Chesapeake Arboretum are top sights worth seeing.

Find hotels in Greenbrier

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 SARĀ 231 per night from Jul 27 to Jul 28
SARĀ 231
SARĀ 273 total
27 Jul - 28 Jul
includes taxes & fees
7.2/10 Good! (882 reviews)
"I had a terrible stay and I reached out to you guys but in vain."

Reviewed on 12 July 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 658 per night from Jul 26 to Jul 27
SARĀ 658
SARĀ 764 total
26 Jul - 27 Jul
includes taxes & fees
8/10 Very Good! (30 reviews)
"Super clean room-everything new! Beds were very comfortable. Nice kitchen area with essentials-will stay again!"

Reviewed on 12 July 2026

Hyatt Studios Chesapeake
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is SARĀ 438 per night from Aug 9 to Aug 10
SARĀ 438
SARĀ 511 total
9 Aug - 10 Aug
includes taxes & fees
9.6/10 Exceptional! (132 reviews)
"The facility was spotless and the staff made check-in easy. My room was very comfortable and the space was alive but peacefully quiet. Aside from seeing other people there, I barely knew anyone else was there in the building. There was plenty of parking and no matter what time of day or night, I ..."

Reviewed on 11 July 2026

YourSpace Hotels Chesapeake
See all 3,439 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.

Stay near popular Chesapeake attractions

A CVS store with a large archway and a red star logo.

Greenbrier Mall

8.4/10 (837 reviews)
This regional shopping center features over 100 stores and eateries, plus a Cinema CafƩ for dining during movies. Families enjoy the supervised soft play area and convenient amenities while shopping.
See properties

Frequently asked questions

How much does a Chesapeake vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation to Chesapeake costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chesapeake?
You can generally find reduced prices and better availability in January, February and November. Explore our cheap Chesapeake vacation packages and you could get some great off-season deals.
How to find the best Chesapeake package deals?
Start your search for a Chesapeake package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Chesapeake package deal right away, just play around with your dates and search again. Remember 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 Chesapeake escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Chesapeake?
If you have your Chesapeake vacation dates finalized, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Chesapeake?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chesapeake.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chesapeake.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Chesapeake vacation package that brings all your bookings together.