Pittsfield Vacation Rentals

Our Favorite Vacation Rentals in Pittsfield

  • Heart Of The Berkshires
     Home/Apartment
    Booking.com
    From
    $155
  • Tentrr - Living Water Campsites: Ski N' Zip 1
     Country House
    Booking.com
    From
    $109
  • Berkshire Cottage
     Country House
    Booking.com
    From
    $695
  • Tentrr - Living Water Campsites: Ski N' Zip 2
     Country House
    Booking.com
    From
    $109
  • Holiday Cottage
     Country House
    Booking.com
    From
    $500
  • Writers Cottage
     Country House
    Booking.com
    From
    $425
  • Greylock Cottage
     Country House
    Booking.com
    From
    $500
  • HawksNest: quiet 2BR apt, heart of the Berkshires
    Excellent2br Home/Apartment
    Airbnb
    From
    $90

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
    $188
  • Wyndham Bentley Brook * 2BR Deluxe
    Excellent2br Home/Apartment
    Airbnb
    From
    $236
  • Beautiful 2BD Villa in Berkshires Resort
    Good2br Home/Apartment
    Airbnb
    From
    $163

Pittsfield Vacation Rentals with Wi-Fi

  • Sharon's Place 4 ..... pets, and 420 friendly!!!!
    GoodHome/Apartment
    Airbnb
    From
    $66
  • Marie's Place
    Excellent2br Home/Apartment
    Airbnb
    From
    $102
  • Central Berkshires - comfy beds and fast internet!
    Excellent3br Home/Apartment
    Airbnb
    From
    $119
  • Charming Sears cottage near lake
    Excellent3br Home/Apartment
    Airbnb
    From
    $189

Pittsfield Pet-Friendly Vacation Rentals

  • Big Beautiful House By The Lake W/Jetted Hot Tub
    Excellent8br Home/Apartment
    Airbnb
    From
    $509
  • SUMMER Cottage in the Berkshires
    Excellent2br Home/Apartment
    Airbnb
    From
    $172
  • Berkshire beautiful one floor house
    ExcellentHome/Apartment
    Airbnb
    From
    $225
  • Berkshires Waterfront Lakehouse
    Excellent3br Home/Apartment
    Airbnb
    From
    $251

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
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
79° 27°
3
64°
6
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
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

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Vacation Rentals in Pittsfield

At AllTheRooms.com we have vacation rentals from all of the leading providers - Airbnb, Priceline, Agoda and more. We have 334 vacation rentals, hotels and other accommodation types in Pittsfield ranging from inexpensive options to extravagant places to stay. For those trying to save money, the cheapest place to stay in Pittsfield comes in at $10 a night. On average, a place to stay in Pittsfield will cost you $161 per night.

Those needing to get some work done during their trip to Pittsfield can choose from 130 places to stay that have WiFi. We have 28 accommodations that come with breakfast included. Choose from 16 places to stay that provide gym options, so you don'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 17 accommodations that have a pool or jacuzzi.

AllTheRooms has 28 pet-friendly places to stay in Pittsfield, so if you're traveling with your pet you won't have any problems.

In Pittsfield AllTheRooms currently compares hotels, vacation rentals, hostels from more than 4 providers, including 130 places to stay from Airbnb, 4 accommodations from Priceline and 4 places to stay from Agoda.

177 of the places to stay in Pittsfield have been reviewed by previous guests. They rated 68% as excellent or good. 100 accommodations allow instant booking.

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