Chesapeake Resorts & All Inclusive Resorts

Discover the 170 Best Resorts in Chesapeake

About Chesapeake Resorts on PickleTrip

PickleTrip™ makes it easy to compare and book resorts in Chesapeake. You can filter your search by location, price, amenities, and more to find the perfect resort for your needs. Our user-friendly website allows you to view detailed descriptions, photos, and customer reviews of each resort, so you can make an informed decision before booking. Additionally, we offer special deals and discounts on many resorts, so you can save money on your next vacation.

Whether you're looking for a romantic getaway or a family vacation, you'll find the perfect resort on PickleTrip™. We also have a great selection of all-inclusive resorts, where everything from meals to activities is included in the price. This can be a great option for those who want to relax and not have to worry about budgeting for extra expenses. Browse our selection of resorts today and start planning your next trip to Chesapeake.

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Frequently Asked Questions About Chesapeake Resorts

There are a lot of options in Chesapeake. If you plan on staying in the Chesapeake area, consider making a reservation for a few nights at one of these properties as these have been rated the top Resort Rentals in Chesapeake:

Most of our listed resorts are suitable for families in Chesapeake. Filter your all-inclusive resorts Chesapeake with a family-friendly option to see which ones are right for you.
Yes, there are more than 170 resorts in Chesapeake that have indoor and private swimming pools. Check out our filter option and find your best resort near Chesapeake.
At PickleTrip, the rate for luxury resorts in Chesapeake per night starts from $47. Our partner provides these prices & we calculated the average daily rate in Chesapeake. Please see our partner's price for more details.
Yes. We have all-inclusive resorts in Chesapeake that allow pets. Some of the top pet-friendly resorts in Chesapeake are:

You can see all pet-friendly places to stayin Chesapeake on PickleTrip

Most of the resorts are perfect for travelers, but based on guest reviews in 2025, the best resorts in or near Chesapeake are:
Some of the resorts in Chesapeake have been described as romantic by other travelers: