Find the best place to stay — Pittsfield

Where to stay around Pittsfield?

Our 2018 property listings offer a large selection of 552 vacation rentals near Pittsfield. From 258 condos to 191 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Pittsfield for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Pittsfield?

HomeAway offers a large selection of vacation rentals near lovely places in Pittsfield. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Okemo Mountain Resort: 1,190 vacation rentals
  • Killington Ski Area: 1,176 vacation rentals
  • Pico Mountain Resort: 1,033 vacation rentals
  • Killington Resort: 1,181 vacation rentals
  • Silver Lake State Park: 807 vacation rentals

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

Can I rent condos in Pittsfield?

Yes, of course. HomeAway has 258 condos in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Houses: 191 rentals available
  • Townhomes: 52 rentals available
  • Chalets: 12 rentals available

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

Can I rent skiing rentals in Pittsfield?

Absolutely, HomeAway has 459 skiing rentals in Pittsfield. You have also many other possibilities in Pittsfield area, including:

  • Golf rentals: 448 rentals
  • Mountain rentals: 380 rentals
  • Waterfront rentals: 12 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 281 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.

    Why People Love Visiting Friendly Pittsfield

    Learn about the unique charm of Pittsfield with a stay in a vacation home rental. This welcoming city allures visitors with its pubs and restaurants. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

    Attractions In and Around Pittsfield

    First time in Pittsfield and looking for places to see? Winter activities you might appreciate include visiting Killington Resort. You may also want to visit Lefferts Pond, White River Golf Club or Green Mountain National Golf Course.