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Pittsfield Vacation Rentals

Pittsfield, Massachusetts Travel Guide

Pittsfield is a bubbly, lively city and is the historic county seat of Berkshire County. It is peaceful and secure, making it abundant with young families. It also has a great ranking as one of the best small towns for businesses to succeed in. Recently the city has seen a surge in culture as the arts, humanities, and sciences have all been growing. It houses the Colonial Theatre which was named by Hillary Clinton as a National Historic Treasure in 1998 and has been described as “one of the finest theatres in the world”.

Things to Do in Pittsfield, Massachusetts

There are quite a number of fun and exciting things to do in Pittsfield, Massachusetts and one of the most popular is visiting the Berkshire Museum. This museum brings families and friends together for a wonderful and educational experience of natural history, art, and ancient civilization. Here, visitors can explore and discover fine art, sculptures, organic specimens, and ancient artifacts all on display.

Another fun activity for the adventurous winter spirit is a trip to the Bousquet Ski Area, a collection of slopes for skiing and snowboarding in the winter. Pittsfield State Forest is another great outdoor destination, perhaps for warmer weather, where one can take a walk past streams, waterfalls, lush vegetation, and enjoy stunning views from the top of Berry Mountain.

Pittsfield is also the location of Arrowhead: The Herman Melville House where guests can take tours of the house and grounds of the famous Moby Dick author’s home.

The Herbert Arboretum is an interesting spot, as people can enjoy a fine collection of plant life while also enjoying a view of Lake Onota. Lake Onota is a great place to stop because it has a fishing pier and a boat ramp, plus a lot of water activities, including rowing, sailing and swimming.

For a lunch or dinner, Mission Bar and Tapas is a great destination. Up near the mountain is Brook Farm Inn, which has some tasty dishes and a nice atmosphere.

Best Time to Visit Pittsfield, Massachusetts

The temperatures from June to September are definitely the most enjoyable, but as we mentioned there is some nearby winter activities so those wanting a taste of powder should come through in the winter.

Price and Availability in Pittsfield

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The most expensive month to stay in a vacation rental in Pittsfield is in July, while the cheapest month is in November. The most popular time to book a vacation rental in Pittsfield is in the high season in August. Pittsfield has its low season in November, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Pittsfield tends to be Tuesday, while the most expensive day tends to be Friday. Vacation homes in Pittsfield tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Pittsfield

67º 18º
3.63
86º 40º
2.56
91º 42º
3.42
93º 46º
4.68
90º 51º
8.25
89º 40º
6.89
79º 27º
2.84
64º
6.39
59º
3.94
61º -10º
4.66
73º -3º
4.09
55º
2.35
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Rainy days
This climate histogram shows you the weather patterns in Pittsfield. The hottest month in Pittsfield is June, when temperatures peak at 93 ˚F. The coolest month is January, when temperatures drop to -10 ˚F. The wettest month in Pittsfield is August with 8.25 inches of rain, while the driest month is March with 2.35 inches of rain.

What Expert Travelers Think

Vacation Rentals in Pittsfield

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, priceline and more. AllTheRooms has 293 vacation rentals, hotels and other great places to stay during your time in Pittsfield, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those trying to keep costs down, the lowest priced place to stay in Pittsfield comes in at $10 per night. On average, a place to stay in Pittsfield will cost you $150 per night.

If you need an internet connection during your stay in Pittsfield, then you can choose from over 109 places to stay that provide WiFi internet. 23 of our accommodations in include a breakfast in the price. Fitness addicts can get a workout in during their stay by choosing from 18 accommodations that have gym facilities. If you're planning on arriving in Pittsfield by car, be sure to choose from 112 accommodations that provide parking. 14 accommodations come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 27 accommodations that are designated as pet-friendly.

We combine a wide variety of Pittsfield accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 6 providers, including 93 places to stay from Airbnb, 14 accommodations from VRBO and 6 places to stay from priceline.

147 of our places to stay in Pittsfield have been rated by previous guests. They rated 65% as excellent or good. You can instantly book any of 70 places to stay right now.

Destinations near Pittsfield