What are the top rated Pet Friendly Vacation Rentals in Chester?

There are a lot of options in Chester. If you plan on staying in the Chester 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 Chester: Cozy Waterfront Apartment Chester, MD Holiday Inn Express Annapolis East-Kent Island by IHG Waterfront House: Hot Tub, Fire Pit, & Views Best Western Kent Narrows Inn Hilton Garden Inn Kent Island Marina Wade a Minute Chester LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12 Stunning views and Sunsets from this waterfront property -Kent Island area Waterfront Getaway on Cox Creek Bentons Pleasure- Cox Creek, Pier and Sunsets!

How many pet-friendly vacation rentals are available in Chester on SunSkiResorts?

There are more than 14 pet-friendly rentals available on SunSkiResorts. Check prices and availability in Chester and last updated on November 2025. Check an individual property if they have restrictions on the size or numbers of pets.

Which is the best dog-friendly place to stay in Chester?

There are many dog-friendly vacation homes available in Chester. Here are the most popular pet-friendly places, ranked by their guest rating as listed in Chester: Cozy Waterfront Apartment Chester, MD Holiday Inn Express Annapolis East-Kent Island by IHG Waterfront House: Hot Tub, Fire Pit, & Views Wade a Minute Chester

Do you have any luxury vacation homes that allow pets in or near Chester?

Most definitely! There are many luxury places to stay in Chester. 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 Chester. Though note, more expensive is not always better.

What is the price of a pet-friendly rental in Chester, Maryland?

The average price of a pet-friendly vacation home is $610 . Find our pet-friendly accommodation near Chester.

What are the most family-friendly holiday rentals near Chester?

At SunSkiResorts, many of our accommodations are perfect for families and allow dogs too. Check out the complete list of pet-friendly holiday rentals in Chester to find what works for you.