Photo by Caitlin Reese

The Berkshires pet-friendly rentals

We found 560 pet-friendly rentals — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any pet-friendly holiday rentals in The Berkshires?
Definitely. There are 560 pet-friendly holiday rentals around The Berkshires to choose from. Whether you're visiting a renowned city like Great Barrington, Hancock or Lanesborough, or enjoying as much as you can on a road trip, we'll help you and your furry companion find your pawfect escape.
How much does it cost to stay in a pet-friendly holiday rental in The Berkshires?
A range of factors will influence the price of a pet-friendly holiday rental in The Berkshires, such as property size and how long and when you plan to stay. All you have to do is key in your travel dates and any preferences to find a house that suits you and your furry friend.
When is the best time to book a pet-friendly holiday rental in The Berkshires?
May is when most Stayz guests get a pet-friendly holiday rental in The Berkshires. Expect average temperatures of between 8ºC and 19ºC if you travel during this time of year.
Where can I rent a pet-friendly holiday rental with great views?
Stayz makes it simple to find the terrific views you're looking for in your pet-friendly holiday rental. Just use our "Location" filter to narrow down the type of area you and your four-legged friend prefer to be in, and the views you want to immerse yourself in, while searching holiday home rentals in The Berkshires.
Do any pet-friendly holiday rentals in The Berkshires have a garden?
You can search for pet-friendly holiday rentals in The Berkshires that include an outdoor space for your dog to play, roam and explore. Stay in one with an enclosed yard or that's close to dog-friendly parks, trails or other recreational areas. To find these types of stays, click on "Garden or backyard" under the features and amenities section of our filter tool.
Can I book a pet-friendly cabin or lodge in The Berkshires?
Get out into nature with your furry companion right by your side at one of our pet-friendly cabins or lodges in The Berkshires. Use our handy "Pet-friendly" filter to narrow your search for Stayz properties that offer an unforgettable experience for the whole family — pooches included.
What are the top things to do in The Berkshires?
There are so many exciting experiences to be had when you book a pet-friendly holiday rental in The Berkshires. The kind of things you're interested in and where you can visit with your furry companion will help you decide what activities to do, so do a little research before you set off.
Why should I book my pet-friendly holiday rental with Stayz?
With our handy filter tool, booking an adventure with your pooch has never been simpler. Tailor your search for the ideal pet-friendly holiday rental by things like location, budget and amenities. Our Book with Confidence guarantee also means that you'll get payment protection and 24/7 customer support during your trip. For more peace of mind, choose one of our rentals that have flexible cancellation policies.