We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Pittsfield Holiday Rentals

Hotels (9)

B&Bs / Inns (4)

Speciality Lodging (1)

Holiday Rentals (2)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed

Add your property »

Other Destinations
Popular Berkshires Destinations
Stockbridge Holiday Rentals (1)
Nearby listings
Renovated Early 1800s Greek Revival Farmhouse, Stockbridge
Renovated Early 1800s Greek Revival Farmhouse
    Price: £125/night £815/week £2,194/month
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 2
  • Min stay: 2
    • Contact Owner

Search Pittsfield Holiday Rentals

Clear dates

Advanced Search

Holiday rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]

There are no holiday rentals within Pittsfield, Massachusetts. We broadened your search to include all rentals within 40 kilometers.

Private, Spacous and Beautiful Ground Floor Apt, Pownal
Private, Spacous and Beautiful Ground Floor Apt
Contact Owner
Nightly rate from
£85
Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 1
Recently renovated 2 bedroom (sort of) fully-appointed, secluded apartment with full kitchen and laundry - only rental unit in barn complex housing gallery, ...
  • Nightly
    £85
  • Weekly
    £502
  • Monthly
    --
Renovated Early 1800s Greek Revival Farmhouse, Stockbridge
Renovated Early 1800s Greek Revival Farmhouse
Contact Owner
Nightly rate from
£125
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 2
Min stay:2
Welcome to our family get-away which we also rent. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short ...
  • Nightly
    £125
  • Weekly
    £815
  • Monthly
    £2,194
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns