Where to stay near Pittsfield?

Our 2020 accommodation listings offer a large selection of 487 holiday rentals near Pittsfield. From 372 Houses to 64 Condos/Apartments, find unique holiday homes for you to enjoy a memorable stay with your family and friends. The best place to stay near Pittsfield for a long holiday or a weekend break is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Pittsfield? offers a large selection of holiday homes near great places in Pittsfield. From travellers, the most popular points of interest to stay near are:

  • Herman Melville's Arrowhead: 489 holiday rentals
  • Pittsfield State Forest: 423 holiday rentals
  • Guido's Marketplace: 496 holiday rentals
  • Arrowhead Museum: 488 holiday rentals
  • Canoe Meadows Wildlife Sanctuary: 483 holiday rentals

But there are many other points of interest around Pittsfield listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Pittsfield?

Yes, of course. offers 372 Houses in Pittsfield. Our other popular types of Pittsfield holiday rentals include:

  • Condos/Apartments: 64 holiday houses
  • Cottages: 51 holiday houses
  • Cabins: 51 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool in Pittsfield?

Yes, you can select your preferred holiday accommodation with pool among our 104 holiday homes with pool available in Pittsfield. Please use our search bar to access the selection of holiday rentals available.