Pittsfield, MA Vacation Rentals: house rentals & more

Discover a selection of 500 vacation rentals in Pittsfield, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $90 per night, and houses and condos are popular options for a stay in Pittsfield. Either way, you'll find a rental for everyone's needs.

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Find the best place to stay — Pittsfield

Search 600 vacation rentals

Stayed Jul 2021

Multigenerational Vacation

This house wonderfully accommodated our multigenerational family (ages 10 months to 61 years). The house was clean, well-equipped and newly renovated. The floor plan made great use of the space. The area is quiet and peaceful with beautiful views of ...

Stayed Jul 2021

Wonderful wildlife!

A repeat visit! The cabin was great - everything we needed. We sat at the lake most of the time - even when raining. Osprey, a magnificent eagle, kingfishers, Great Blue Herons, Green Heron, beavers, frogs, rabbits - all came to visit. Paddling was s...

Stayed Jul 2021

Great property!

We had a great stay here! The location is great - right on the water and we enjoyed using the kayaks and the kids were able to jump off the dock and swim around the shallow area. Recommend water shoes since it’s rocky on the bottom. House has everyth...

Stayed Jun 2021

First time visit to the little red schoolhouse

This was my first time renting a house while traveling. I did this to bring along my dog on vacation. It turned out this was an adorable house with the perfect blend of new conveniences and maintenance of the building’s history. It was located near m...

Stayed Jun 2021

nice place to relax

If you like the outdoor and country side this is a perfect place to relax. It is a nice house and great location. We really needed to bring only our personal things. Everything else is there. Some equipment (especially the outdoor) and the screened ...

Stayed Jun 2021

Great stay!

The property has a great location - right on the lake and centrally located with easy access to Williamstown, Great Barrington, Stockbridge, various waterfalls, etc. The highlight of the house is the big screen porch overlooking the lake. The 2 kids ...

Stayed Jun 2021

Lovely location, fine house

The property has been renovated to accommodate a large number of people comfortable. Light, airy, clean, with both a lovely view of the lake to the east, and a large expanse of lawn down to the lake and dock, the house is a fine vacation spot for a l...

Stayed Jun 2021

Beautiful Berkshires Stay

Rhonda’s home was beautiful. It was right on the lake and the home was clean and had everything you needed. The views were incredible. It was conveniently located where it was close to shops and restaurants. Highly recommend this place and will be ba...

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Destination guide

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

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)

Natural features

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)

How to get there

Traveling to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you'd rather travel by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

How many vacation rentals are available around Pittsfield, MA?

Our 2021 property listings offer a large selection of 600 vacation rentals around Pittsfield. From 436 house rentals to 84 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Pittsfield?

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

Pittsfield Station: 502 vacation rentals
Canoe Meadows Wildlife Sanctuary: 404 vacation rentals
Berkshire Athenaeum: 528 vacation rentals
Herman Melville's Arrowhead: 549 vacation rentals
Berkshire Museum: 532 vacation rentals

But there are many other points of interest around Pittsfield listed on Vrbo 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. Vrbo has 436 Houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

Condos/Apartments: 84 rentals available
Cabins: 61 rentals available
Cottages: 55 rentals available

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

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 141 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.