Where to stay around Pittsfield?

Our 2018 property listings offer a large selection of 693 vacation rentals near Pittsfield. From 398 Houses to 119 Condos/Apartments, 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:

  • Colonial Theater: 634 vacation rentals
  • Canoe Meadows Wildlife Sanctuary: 634 vacation rentals
  • Berkshire Museum: 630 vacation rentals
  • Pittsfield Station: 592 vacation rentals
  • Arrowhead Museum: 646 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 Houses in Pittsfield?

Yes, of course. HomeAway has 398 Houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos/Apartments: 119 rentals available
  • Cabins: 70 rentals available
  • Cottages: 70 rentals available

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

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 171 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.

    Explore the lakeside setting in Pittsfield

    Take a vacation to Pittsfield and enjoy the area's entertainment, theater scene and opera. Renowned for its baseball games, museums and biking, this city welcomes all visitors. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

    Activities and attractions in Pittsfield

    Are you looking for attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Pittsfield has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

    • Bousquet Ski Area (2.3 mi / 3.7 km)
    • Kennedy Park (4.7 mi / 7.6 km)
    • Pleasant Valley Wilderness Sanctuary (5.1 mi / 8.2 km)
    • Bas Ridge Golf Course (6.8 mi / 10.9 km)
    • Wood's Pond (7 mi / 11.3 km)
    • Furnace Brook Winery at Hilltop Orchards (7.6 mi / 12.3 km)

    Exploring the natural landscape of Pittsfield

    Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Pittsfield. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

    • Canoe Meadows Wildlife Sanctuary (1.5 mi / 2.3 km)
    • Pittsfield State Forest (4.5 mi / 7.3 km)
    • Kennedy Park (4.7 mi / 7.6 km)
    • Wood's Pond (7 mi / 11.3 km)
    • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
    • Wahconah Falls State Park (7.6 mi / 12.3 km)