Photo by Caitlin Reese

The Berkshires rentals with pool

We found 596 rentals with pool — 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 holiday rentals with a pool in The Berkshires?
Pick from 596 holiday rentals with a pool in The Berkshires. Take the family on a fun-filled trip to Great Barrington or explore other vibrant cities like Hancock and Lanesborough. Wherever you're going and whether you want to swim or just lounge poolside, Stayz has your perfect stay.
How much does it cost to stay in a holiday rental with a pool in The Berkshires?
A range of factors will influence how much you pay for a holiday rental with a pool in The Berkshires, such as the size of the property and when and how long you plan to stay. All you need to do is key in your travel dates and preferences to find a house where you can splash around in.
When is the best time to book a holiday rental with a pool in The Berkshires?
It all depends on what you plan to see and if you want to visit in peak, shoulder or low season. May is when most Stayz guests book a holiday rental with a pool in The Berkshires. Average temperatures during this time range between 8ºC and 19ºC.
What holiday rentals with a pool in The Berkshires have nice views?
Use our convenient "Location" filter to find a holiday rental with a pool and the views you're looking for. Start by entering the dates you plan to visit The Berkshires, then narrow your options based on the type of area you'd rather stay in. The only thing left is to pack your swimwear and you're all set for a splashing great time.
Are there holiday rentals with a private pool in The Berkshires?
Morning, afternoon or evening, enjoy a refreshing swim whenever you please when you book a holiday rental with a private pool in The Berkshires. To find stays that'll boost the fun factor during your escape, use our "Private pool" filter.
What are the top things to do in The Berkshires?
With an abundance of things to see and do in The Berkshires, you're bound to have a fantastic escape. Not sure where to start? Look up travel websites or think about hiring a knowledgeable guide. After a busy day taking in the sights, go for a swim or just kick back poolside with your loved ones in one of our holiday home rentals.
Why should I book my holiday rental with a pool with Stayz?
Whether you're travelling as a couple or with a group of pals, staying at a holiday rental with a pool offers another level of relaxation and fun to your break. And finding the right pad is a breeze with our handy filters. Simply narrow your search by amenities, location, budget and more, then choose your favourite. Another superb reason to book with us is our flexible cancellation policies. If you need to change plans, you'll receive a 100% refund as long as you cancel within the property owner's specified time frame.