Pittsfield Vacation Rentals

Our Favorite Vacation Rentals in Pittsfield

  • Villa with Access to 2 Pools, a Hot Tub, an 18-Hole Mini Golf Course, and More
     Villa
    RedAwning
    From
    $159
  • Berkshire Cottage
     Country House
    Booking.com
    From
    $800
  • Lake House w/ Deck & Views, Mins to Jiminy Peak!
     3br Cottage
    HolidayLettings
    From
    $675
  • Spacious Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna!
     2br Villa
    RedAwning
    From
    $232
  • Holiday Cottage
     Country House
    Booking.com
    From
    $550
  • Berkshires Waterfront Lakehouse Sanctuary
    Good3br Home/Apartment
    HolidayLettings
    From
    $310
  • Villa with Access to Pools, a Hot Tub, Mini Golf, and a Sauna! Great Location!
     2br Villa
    RedAwning
    From
    $208
  • Writers Cottage
     Country House
    Booking.com
    From
    $500

Check prices for these upcoming dates

Pittsfield Vacation Rentals with a Pool

  • Charming Apartment inThe Heart of The Berkshires 2
    ExcellentHome/Apartment
    Airbnb
    From
    $170
  • The Oliver Wendell Holmes Guesthouse @ Holmesdale
    ExcellentHome/Apartment
    Airbnb
    From
    $324
  • Berkshires Jiminy Peak Mountainside Condo
    Excellent2br Home/Apartment
    Airbnb
    From
    $408
  • WALK to TNGLWD, Htd Pool, Hot Tub, S Bowl w/ Boats
     5br Home/Apartment
    Airbnb
    From
    $1,009

Pittsfield Vacation Rentals with Wi-Fi

  • The Best Neighborhood in Pittsfield
    Excellent2br Home/Apartment
    Airbnb
    From
    $141
  • Lovely Apartment in Historic Berkshire Victorian 1
    OkayHome/Apartment
    Airbnb
    From
    $181
  • Beautiful Berkshire County Apartment
     Home/Apartment
    Airbnb
    From
    $85
  • BEAUTIFUL 4BDRM COLONIAL HOME Berkshire getaway
     4br Home/Apartment
    Airbnb
    From
    $192

Pittsfield Pet-Friendly Vacation Rentals

  • 2200sf Country House on 16 Acres-2 Miles to Jiminy
    Good4br Home/Apartment
    HolidayLettings
    From
    $487
  • Family Home w/ Game Room - 3 Miles to Jiminy Peak!
     4br Home/Apartment
    HolidayLettings
    From
    $550
  • 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
60° -5°
3
67°
1
74° 19°
5
83° 36°
4
85° 39°
5
90° 51°
4
86° 43°
2
85° 34°
3
73° 29°
8
66° 11°
4
53°
5
54° -11°
5
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
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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    Jeff CampbellMiddle Class Dad
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Vacation Rentals in Pittsfield

Pick the perfect rental for your vacation at AllTheRooms.com. We aggregate Airbnb, Priceline, Agoda and others. Pittsfield has 297 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. If you are wanting to save money, the lowest priced place to stay in Pittsfield is just $10 a night. In general, an accommodation in Pittsfield will cost you $151 per night.

Those needing to get some work finished during their trip to Pittsfield can pick from 129 places to stay that provide WiFi. We have 25 accommodations that come with breakfast included. Choose from 12 places to stay that provide gym facilities, so you don't miss a single workout. If you are driving to Pittsfield, you'll want to pick from 135 places to stay that provide parking. We track 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 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 127 places to stay from Airbnb, 8 accommodations from Priceline and 5 places to stay from Agoda.

160 of our rentals in Pittsfield have been rated by previous guests. They rated 66% as great. 83 accommodations allow instant booking.

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