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
86° 49°
11
89° 48°
5
82° 40°
7
74° 28°
8
65° 14°
3
63° 14°
4
38° -5°
2
46°
2
73°
3
73° 20°
5
87° 34°
5
90° 41°
3
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days

This climate histogram shows you the weather patterns in Pittsfield. The warmest months in Pittsfield are July and May, when temperatures reach 90 ˚F. The coolest month is December, when temperatures drop to -5 ˚F. The wettest month in Pittsfield is June with 10.75 inches of rain, while the driest month is December with 1.68 inches of rain.

What Expert Travelers Think

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    Jeff CampbellMiddle Class Dad
  • — 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

    Jaz
    JazThe Life of a Social Butterfly
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
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Vacation Rentals in Pittsfield

Find the perfect vacation rental for your vacation at AllTheRooms.com. We compare Airbnb, Priceline, Agoda and more. AllTheRooms has 300 vacation rentals, hotels and other great places to stay while you enjoy Pittsfield, with everything from cheap hostels and homestays to extravagant Airbnbs and hotels. When traveling on a budget, the cheapest place to stay in Pittsfield is available at $10 per night. In general, a place to stay in Pittsfield will cost you $148 per night.

If you need to stay connected during your trip, then you can choose from over 131 accommodations in Pittsfield that have WiFi. 25 places to stay include a morning meal. Choose from 12 places to stay that provide gym options, so you won't miss a single workout. Driving to Pittsfield? Then choose one of the 137 places to stay that comes with a parking spot included. We have 16 accommodations that have 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, home stays, hostels and other unique places to stay into one easy search. We show results from more than 3 providers, including 129 places to stay from Airbnb, 8 accommodations from Priceline and 5 places to stay from Agoda.

167 of the rentals in Pittsfield have been rated by previous guests. They rated 65% as great. 87 places to stay in are instantly bookable.

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