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

There are more than 19 pet-friendly rentals available on Outdoorplaces. Check prices and availability in Chester and last updated on January 2026. 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: Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating Berkshire Vacation Rentals: Pristine Home In Becket Woods Berkshires Lakefront Retreatn Cozy Berkshires Vacation Rental Near Hiking!

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, Massachusetts?

The average price of a pet-friendly vacation home is $365 . Find our pet-friendly accommodation near Chester.

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

At Outdoorplaces, 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.

Pet Friendly Vacation Rentals in Chester

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

From US $171

9.6 (232 Reviews)

Cabin

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Air Conditioner
Parking
Pet Friendly

Chester Pet Friendly Vacation Rentals & Homes

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

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