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  3. Norfolk - Virginia Beach
  4. Chesapeake
  5. Pet Friendly Vacation Rentals

Chesapeake Pet Friendly Vacation Rentals & PickleTrip Homes

Book a Dog-Friendly Rental in Chesapeake for Your Next Adventure

About Chesapeake Pet Friendly Vacation Rentals on PickleTrip

PickleTrip™'s pet-friendly rentals in Chesapeake are perfect for pet owners who want to bring their furry friends and enjoy their next pickleball game on vacation. You can rest easy knowing that your pet is welcome and comfortable in your rental. With a variety of options to choose from, you can find the perfect accommodation that fits your needs and budget. Whether you're looking for a cabin in the woods, a beachfront villa, or a luxury resort, PickleTrip™ has a pet-friendly rental that will suit your needs.

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Frequently Asked Questions About Chesapeake Pet-Friendly Rentals

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 Pet Friendly Vacation Rentals in Chesapeake:

There are more than 45 pet-friendly rentals available on PickleTrip. Check prices and availability in Chesapeake and last updated on October 2025. Check an individual property if they have restrictions on the size or numbers of pets.
There are many dog-friendly vacation homes available in Chesapeake. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Chesapeake:
Most definitely! There are many luxury places to stay in Chesapeake. Use our search filter to discover all of our luxury accommodations where pets are welcome, then choose the one that matches your taste. Sorting by price is another way to find the most expensive dog-friendly home in Chesapeake. Though note, more expensive is not always better.
The average price of a pet-friendly vacation home is $227. Find our pet-friendly accommodation near Chesapeake.
At PickleTrip, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Chesapeake to find what works for you.