A historic building with classical architecture, a traffic light, and a yellow taxi.

Pittsfield cottage rentals

We found 54 cottage rentals — enter your dates for availability

Explore Pittsfield cottage rentals

Image of Lake Views & Dock Access - Pittsfield Cottage!

Lake Views & Dock Access - Pittsfield Cottage!

Sleeps 6 · 4 bedrooms · 1+ bathroom

Image of Charming Lakeview Cottage in Heart of the Berkshires

Charming Lakeview Cottage in Heart of the Berkshires

Sleeps 5 · 1 bedroom · 1 bathroom

Image of Charming historic cottage on scenic road to Mt. Greylock

Premier Host

Charming historic cottage on scenic road to Mt. Greylock

Sleeps 5 · 2 bedrooms

Image of Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Premier Host

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Sleeps 4 · 1 bedroom · 1 bathroom

Image of Berkshire Lake House Private Dock Sleeps 6

Berkshire Lake House Private Dock Sleeps 6

Sleeps 6 · 3 bedrooms · 1+ bathroom

Image of Charming Lenox Cottage with AC - Walk to Town! New!

Charming Lenox Cottage with AC - Walk to Town! New!

Sleeps 5 · 3 bedrooms · 2 bathrooms

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Enjoy full kitchens, laundry, pools, gardens and more
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