Find the best Pittsfield vacation rentals on Tripping.com. With over 101 home rentals, take your pick from a wide variety of choices including studio apartments, luxury condos, and cozy cabin rentals. Prices in Pittsfield range from $40 a night. Many rentals can also be booked directly online.Vacation home rentals found on Tripping.com offer more amenities than the average hotel room along with many of the comforts of home. Going on a business trip or need to stay connected? 77 homes in Pittsfield offer high-speed WiFi Internet so you won’t miss a beat. Travelling with kids? Let them splash around in any of the 33 rentals with pool or jacuzzi, or relax with the family in one of the 72 homes with cable TV.For all those pet owners with dogs or cats, Pittsfield offers 15 pet-friendly vacation rentals for your extended family. Find the perfect vacation rental that matches your budget and style on Tripping.com.Search properties from 6 vacation rental sites in Pittsfield where the top providers in that area are HomeAway, Booking.com, and Expedia. There are 27 HomeAway rentals, 23 Booking.com short term rentals and 20 Expedia vacation rentals.