Pittsfield holiday rentals
We found 963 holiday rentals — enter your dates for availability
If you'd like to stay close to Pittsfield, MA (PSF-Pittsfield Municipal), take a look at private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include air conditioning and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Pittsfield, MA (PSF-Pittsfield Municipal)
Showing deals for:7 Nov - 14 Nov
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails

10 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is S$6,381
S$912 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Pittsfield

Private Berkshire Cabin on 27acres near Jiminy Peak.
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.6 out of 10
exceptional
(7 reviews)
Top rated rentals - Pittsfield

Beautiful place, great location
10 out of 10
exceptional
(235 reviews)
The Playhouse was a beautiful and dramatic space to host some close friends and family for our daughter's wedding. Everyone wants to go back next year for the anniversary!
Michael B.
Stayed Sept 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value