Pittsfield Vacation Rentals

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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 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 Fridays, while it tends to be much quieter on Tuesdays.
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 July. Pittsfield has its low season in November, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Pittsfield

Rainy days
90° 51°
4
86° 43°
2
85° 34°
3
73° 29°
8
66° 11°
4
53°
5
54° -11°
5
60° -5°
3
67°
1
74° 19°
5
83° 36°
4
85° 39°
5
Jul
Aug
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Dec
Jan
Feb
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Apr
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Rainy days

This climate histogram shows you the weather patterns in Pittsfield. The warmest months in Pittsfield are June and May, when temperatures reach 90 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Pittsfield is March with 8.3 inches of rain, while the driest month is October with 1.25 inches of rain.

What Expert Travelers Think

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    Laurelle McVickerLaurelle McVicker
  • — Like the buttons on the calendar which say today, tomorrow - that will make it easy for booking on the road. Website looks great - clean and easy to understand.

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    Samantha WraggCoco Travels
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

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    JazThe Life of a Social Butterfly

Vacation Rentals in Pittsfield

Browse rentals from all the best providers including Airbnb, Priceline, Agoda and more at AllTheRooms.com. AllTheRooms has 300 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 traveling on a budget, the most economical place to stay in Pittsfield is available at $10 per night. The average price of an accommodation is $148 per night.

If you have to have internet access during your stay in Pittsfield, then you can choose from over 131 accommodations that have WiFi internet. We have 25 accommodations that include a breakfast included. Fitness addicts can get a workout in during their stay by choosing from 12 accommodations that have gym facilities. Driving to Pittsfield? Then choose one of the 137 places to stay that comes with a parking spot included. We have 16 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 27 pet-friendly places to stay in Pittsfield, so if you're traveling with your cat or dog you won't have any trouble.

We compare vacation rentals, hotels and other unique accommodation types from many providers in Pittsfield, including 129 places to stay from Airbnb, 8 accommodations from Priceline and 5 places to stay from Agoda

167 of our accommodations in Pittsfield have been reviewed and rated. 65% are rated excellent or good. 87 places to stay in are instantly bookable.

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