Hotels in Pittsfield

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Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Where to stay in Pittsfield?

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very Good, (998)
The price is $88
$99 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
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Budget hotels in Pittsfield and vicinity

Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
The price is $67
$74 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Monument Mountain Motel
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.
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Check out pet-friendly hotels in Pittsfield

Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
The price is $94
$105 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Plus Berkshire Hills Inn & Suites
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You may also like hotels with pools in Pittsfield

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (998)
The price is $88
$99 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
View all properties

When is the best time to visit Pittsfield?

Our prices for hotels in Pittsfield are cheapest in April
Price trends for hotels in Pittsfield
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Pittsfield
December
Moderate crowds
High 2°C / low -5°C. Snow likely.
View properties in December
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December, Moderate crowds, average high temperature 2 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
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January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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February, Moderate crowds, average high temperature 0 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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March, Low crowds, average high temperature 5 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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April, Low crowds, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Cloudy most days.
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May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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June, High crowds, average high temperature 23 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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July, High crowds, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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August, High crowds, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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October, High crowds, average high temperature 14 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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November, Moderate crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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Monthly weather averages (˚C)

Top landmarks in Pittsfield

Hardly anyone here! Great way to spend a week day, skiing and tubing!
Photo by Robin/Loving Life
Open Photo by Robin/Loving Life

Bousquet Ski Area

4.0/5 (23 reviews)
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.
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Hancock Shaker Village, Hancock Massachusetts beautiful place; description Shakers, all supported themselves by the proceeds of their farmland. The Hancock Shakers were primarily dairy farmers. The raising and sale of garden seeds was perhaps the most lucrative of their early businesses.Land acquisition and conversion continued for decades, with the area peaking at 3,000 acres (12 km2) and the population rising to over 300.After reaching peak membership in the 1840s, the Shaker movement gradually dwindled, partially due to the urban migration that accompanied the Industrial Revolution, and by the westward migration of New England's youth. By the early twentieth century, the population of the village had fallen to around 50, most of whom were children. The remaining Shakers sold off their excess land, and many buildings were destroyed.The decision was eventually made in 1960 to close the village and sell the property and buildings. Non-Shakers were impressed by the Hancock Shaker property—scrupulously clean, neat, and well-tended—and their innovations in farming, such as the round barn that attracted much attention Visitors also praised Hancock Shakers' products, including boxes "of beautiful workmanship" and garden seeds. Before 1820, the village was prosperous and the Shakers were respected as good neighbors.
Photo by Ed Gaffny
Open Photo by Ed Gaffny

Hancock Shaker Village

4.5/5 (73 reviews)
If seeing the sights is on your list of things to do, head to Hancock Shaker Village— just one of the landmarks located 4.7 mi (7.6 km) from central Pittsfield. You could also start your cultural experience by heading over to the museums in the area.
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Learn more about Pittsfield

Tucked into the heart of the Berkshires, this cultural powerhouse punches well above its weight. The Berkshire Museum offers an eclectic mix of art, history, and aquarium exhibits that somehow work perfectly together. At the gloriously restored Colonial Theater, performances unfold in a space where the acoustics haven't changed since 1903. Herman Melville wrote 'Moby-Dick' at his home Arrowhead, now open for tours that reveal the author's mountain view that reminded him of a whale's back. The Hancock Shaker Village presents a fascinating glimpse into America's most successful utopian community. Come winter, locals hit the slopes at Bousquet Ski Area, while summer brings outdoor theater at Barrington Stage Company where Broadway shows often premiere before heading to New York.

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Pittsfield featuring a city

Check out reviews of Pittsfield hotels guests love

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Clean and warm, very spacious and cozy. People here are very nice too! Very good experience here. "
lijun 2-night trip
Posted 23 hours ago
Berkshire Mountain Lodge

Frequently asked questions

What accommodations do travelers like in Pittsfield?
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG, Hotel On North and Hilton Garden Inn Lenox Pittsfield 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 should I stay in Pittsfield if I'm looking for a reasonably priced accommodation?
Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn Express & Suites Pittsfield - Berkshires by IHG are two accommodations you might want to consider that'll save you money.
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 40 vacation homes. You can also consider one of the 8 apartments or 9 cottages.
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.