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