Pittsfield Vacation Rentals

Our Favorite Vacation Rentals in Pittsfield

  • Heart Of The Berkshires
    ExcellentHome/Apartment
    Booking.com
    From
    $155
  • Big Beautiful 7 bedroom 3 bath hot tub pool table
     7br Home/Apartment
    HolidayLettings
    From
    $703
  • Berkshire Cottage
     Country House
    Booking.com
    From
    $550
  • Berkshires Waterfront Lakehouse Sanctuary
    Good3br Home/Apartment
    HolidayLettings
    From
    $310
  • Jiminy Peak Vacation Home
     Country House
    Booking.com
    From
    $300
  • NEW! Lenox Home Mins to Tanglewood Shakespeare &Co
     3br Home/Apartment
    HolidayLettings
    From
    $415
  • Tentrr - Birch Berry Pines
     Country House
    Booking.com
    From
    $86
  • Stone School Cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $230

Check prices for these upcoming dates

Pittsfield Vacation Rentals with a Pool

  • Amazing, Spacious Estate on 10 Acres
    Excellent8br Estate
    Airbnb
    From
    $1,342
  • The Oliver Wendell Holmes Guesthouse @ Holmesdale
    ExcellentHome/Apartment
    Airbnb
    From
    $233
  • Idyllic Berkshires Retreat With Pond Views & Pool
    Excellent2br Home/Apartment
    Airbnb
    From
    $279
  • Beautiful 2BD Villa in Berkshires Resort
    Good2br Home/Apartment
    Airbnb
    From
    $163

Pittsfield Vacation Rentals with Wi-Fi

  • Pittsfield Place
    ExcellentHome/Apartment
    Airbnb
    From
    $146
  • Center of Berkshires Apartment
    Nice2br Home/Apartment
    Airbnb
    From
    $124
  • Lovely Apartment in Historic Berkshire Victorian 1
    OkayHome/Apartment
    Airbnb
    From
    $198
  • Charming Sears cottage near lake
    Excellent3br Home/Apartment
    Airbnb
    From
    $189

Pittsfield Pet-Friendly Vacation Rentals

  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good4br Home/Apartment
    HolidayLettings
    From
    $487
  • Heart of the Berkshires!
    Good3br Home/Apartment
    HolidayLettings
    From
    $288
  • The Meadow House 4 bdrm 4 bath house
     4br Home/Apartment
    HolidayLettings
    From
    $753
  • Garfield House
     2br Home/Apartment
    HolidayLettings
    From
    $265

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

Most expensive
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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
79° 27°
3
64°
6
59°
4
61° -10°
5
73° -3°
4
55°
2
67° 18°
4
86° 40°
3
91° 42°
3
93° 46°
5
90° 51°
8
89° 40°
7
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Rainy days

This climate histogram shows you the weather patterns in Pittsfield. The warmest months in Pittsfield are June and July, when temperatures reach 93 ˚F. The coolest month is December, when temperatures drop to -10 ˚F. The wettest month in Pittsfield is May with 8.25 inches of rain, while the driest month is October with 2.35 inches of rain.

What Expert Travelers Think

  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — 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.

    Samantha Wragg
    Samantha WraggCoco Travels
  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims

Vacation Rentals in Pittsfield

Find the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Priceline, Agoda and more. We have 320 vacation rentals, hotels and other accommodation types in Pittsfield ranging from inexpensive options to luxury places to stay. If you are wanting to save money, the cheapest place to stay in Pittsfield is only $10 a night. On average, an accommodation in Pittsfield will cost you $162 per night.

Those looking to get some work finished during their trip to Pittsfield can pick from 136 places to stay that have WiFi. 28 of our accommodations come with breakfast in the price. You can keep up with your workout routine by staying at one of 18 accommodations that provide gym facilities. If you are driving to Pittsfield, you'll want to pick from 142 places to stay that provide parking. We track 17 places to stay that have a pool or jacuzzi.

Those traveling with a dog, cat or some other animal can stay in any of 32 accommodations that are designated as pet-friendly.

In Pittsfield AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 124 places to stay from Airbnb, 4 accommodations from Priceline and 4 places to stay from Agoda.

180 of our accommodations in Pittsfield have been reviewed and rated. 66% are rated excellent or good. 93 accommodations allow instant booking.

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