Hotels in Pittsfield

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Check prices for these dates

Tonight
May 4 - May 5
Tomorrow
May 5 - May 6
Next weekend
May 9 - May 11
In two weeks
May 16 - May 18

Where to stay in Pittsfield?

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (712)
The price is $127
includes taxes & fees
$114 per night
May 12 - May 13
Hotel On North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
trending_down

Our prices for hotels in Pittsfield are cheapest in January

See average prices and weather for all months

Price trends for hotels in Pittsfield

Pricing is based on two traveler single night rates
May
$190
Average price during May is $190
Jun
$222
Average price during June is $222
Jul
$259
Average price during July is $259
Aug
$265
Average price during August is $265
Sep
$225
Average price during September is $225
Oct
$233
Average price during October is $233
Nov
$160
Average price during November is $160
Dec
$162
Average price during December is $162
Jan
$137
Average price during January is $137
Feb
$157
Average price during February is $157
Mar
$161
Average price during March is $161
Apr
$156
Average price during April is $156
Currently viewing crowd sizes and weather for May.

May

trending_downLow crowds
High 66°F / low 47°F. Sunny most days.
66°
weather_sun
May, Low crowds, average high temperature 66 degrees Fahrenheit, average low temperature 47 degrees Fahrenheit. Sunny most days.
47°
74°
weather_sun
June, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 55 degrees Fahrenheit. Sunny most days.
55°
80°
weather_sun
July, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
61°
78°
weather_sun
August, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 60 degrees Fahrenheit. Sunny most days.
60°
71°
weather_sun
September, Moderate crowds, average high temperature 71 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
58°
weather_sun
October, High crowds, average high temperature 58 degrees Fahrenheit, average low temperature 43 degrees Fahrenheit. Sunny most days.
43°
45°
weather_partly_sunny
November, Moderate crowds, average high temperature 45 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Partly sunny.
31°
35°
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December, Moderate crowds, average high temperature 35 degrees Fahrenheit, average low temperature 23 degrees Fahrenheit. Snow likely.
23°
29°
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January, Low crowds, average high temperature 29 degrees Fahrenheit, average low temperature 16 degrees Fahrenheit. Snow likely.
16°
32°
ac_unit
February, Moderate crowds, average high temperature 32 degrees Fahrenheit, average low temperature 17 degrees Fahrenheit. Snow likely.
17°
40°
ac_unit
March, Low crowds, average high temperature 40 degrees Fahrenheit, average low temperature 24 degrees Fahrenheit. Snow likely.
24°
53°
weather_cloudy
April, Low crowds, average high temperature 53 degrees Fahrenheit, average low temperature 35 degrees Fahrenheit. Cloudy most days.
35°
Monthly weather averages (˚F)
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Top landmarks in Pittsfield

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

Why not give yourself a treat with a trip to Bousquet Ski Area, one of the family attractions located 2.6 mi (4.3 km) from central Pittsfield. If you master the slopes, Jiminy Peak Mountain Resort is just a short drive away.

See properties in Bousquet Ski Area
Bousquet Ski Area

Learn more about Pittsfield

Pittsfield is applauded for its entertainment and theater with such cultural attractions as Berkshire Museum and Colonial Theater. Sights include Barrington Stage Company and Bousquet Ski Area and visitors speak highly of the city's sports.

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Pittsfield featuring a city
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Frequently asked questions

What accommodations do travelers like in Pittsfield?
Hotel On North, Hilton Garden Inn Lenox Pittsfield and Best Western Plus Berkshire Hills Inn & Suites are all properties that our guests really like.
Where can I find free parking at my hotel in Pittsfield?
Park your car for free at Holiday Inn & Suites Pittsfield-Berkshires by IHG.
Can I book a refundable hotel in Pittsfield?
If you need the flexibility to change your travel plans to Pittsfield, most properties provide refundable* rates you can book. You can see these accommodations by searching our site and using the “fully refundable” filter to narrow the results down.
Where can I stay with my pet in Pittsfield?
Your furry friend can stay with you at these pet-friendly hotels: Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield. There are 5 options to choose from on our site.
Which Pittsfield hotels do guests like for their great location?
Travelers like these properties for their good location: Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.
Where should I stay in Pittsfield if I'm looking for a reasonably priced accommodation?
An inexpensive option worth considering is Best Western Plus Berkshire Hills Inn & Suites.
Where can I stay in Pittsfield if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, browse our selection of 36 vacation homes. You can also consider one of the 8 apartments or 8 cottages.
Where can I stay if I'm traveling to Pittsfield with my family?
Parents traveling with children may want to consider Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express Pittsfield Berkshires, an IHG Hotel.
Where should I stay in Pittsfield for a vacation with my partner?
Hotel On North is a good option for a romantic getaway with your special someone.
Where should I stay in Pittsfield if I want a luxury accommodation?
An option for a luxury stay is Yankee Suites Extended Stay.
What will the weather in Pittsfield be like during my vacation?
July and August are typically the warmest months in Pittsfield when the average temp is 66°F. January and February are the coldest months when the average temperature is 27°F. October and August are the months with the most rain.
Why should I book my Pittsfield hotel with Hotels.com?
There are lots of reasons to book your Pittsfield trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

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