52 Pittsfield Holiday Rentals

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Compare Pittsfield holiday rentals from 8 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $25 to $3000 a night.

Information about Pittsfield

Vacation Rentals in Pittsfield

Find the best Pittsfield vacation rentals with Tripping.com. Choose from 553 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $3000 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 321 of homes in Pittsfield offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 155 rentals with pool or jacuzzi, or relax with the family in one of the 317 homes with cable TV.

For all those dog lovers and cat lovers, Pittsfield offers 75 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 8 rental sites in Pittsfield where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 237 HomeAway rentals, 170 Booking.com short term rentals and 108 TripAdvisor vacation rentals.