Hotels in Pittsfield

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Tonight
18 Dec - 19 Dec
Tomorrow
19 Dec - 20 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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, (989)
  • cleanliness
    Located in Pittsfield, the hotel offers peaceful rooms near Berkshire attractions.
The price is €98
includes taxes & fees
1 Jan - 2 Jan 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, 2 Queen Beds, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (805)
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 hotels with a pool 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, (989)
The price is €98
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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You may also like pet-friendly hotels in Pittsfield

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
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, (1001)
The price is €72
includes taxes & fees
20 Dec - 21 Dec
Best Western Plus Berkshire Hills Inn & Suites
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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When is the best time to visit Pittsfield?

Our prices for hotels in Pittsfield are cheapest in November
Price trends for hotels in Pittsfield
Pricing is based on two traveller 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.
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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 Theatre, 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 theatre 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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Old time charm and hot tub under the stars"
Lori 2-night trip
Posted 2 days ago
The Red Lion Inn

Frequently asked questions

How much does a hotel room cost in Pittsfield?
You can find top hotels in Pittsfield from €72 with options to suit your budget and needs. Berkshire Inn is one low-cost option that's popular with our travellers. If you're looking for an affordable hotel in Pittsfield that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.
How much does a hotel room cost in Pittsfield?
You can find top hotels in Pittsfield from €72 with options to suit your budget and needs. Berkshire Inn is one low-cost option that's popular with our travellers. If you're looking for an affordable hotel in Pittsfield that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com. If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Pittsfield hotels?
Discover great deals on Pittsfield hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Pittsfield hotels.
How can I find deals and earn rewards at Pittsfield hotels?
Members can save up to 20% on select hotels in Pittsfield. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.

Can I book Pittsfield hotels with free cancellation?
In order to book a refundable Pittsfield hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some top pet-friendly hotels in Pittsfield?
Consider one of our travellers' favourite pet-friendly hotels in Pittsfield:You can check "Pet friendly" on the Hotels.com "Amenities" filter in your search to find even more pet-friendly hotels in Pittsfield.
What are some of the best hotels in Pittsfield for couples?
Choose a top-rated Pittsfield romantic hotel and enjoy your couple's getaway. Our travellers love Holiday Inn & Suites Pittsfield-Berkshires by IHG, a hotel with a restaurant. Discover more hotels in Pittsfield on Hotels.com for couples by using the "Traveller experience" filter in your search and selecting "Adults only" or "Romantic".
What are the top Pittsfield hotels with a pool?
For some added luxury, discover the best Pittsfield hotels with a pool. Hilton Garden Inn Lenox Pittsfield is a great hotel with an indoor pool and a guest rating of 9.2 out of 10. To find more stays in Pittsfield with a pool, use the "Amenities" filter on Hotels.com in your search and select "Pool".
What are some of the best Pittsfield hotels with free parking?
If you're driving, a great Pittsfield hotel with free parking is a bonus. Our travellers' favourites include:
What are some popular hotels in central Pittsfield?
If you're looking for hotels in central Pittsfield, check out Element Lenox Berkshires and Hotel On North. Travellers love Element Lenox Berkshires for its location, as well as the indoor pool, restaurant and bar/lounge this hotel offers. Hotel On North is another popular central hotel with a bar/lounge, free parking and concierge services.
Can I book a refundable accommodation option in Pittsfield?
If you want the flexibility to change your plans to Pittsfield, most hotels offer refundable* rates that you can book. You can see this accommodation by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Pittsfield if I want a holiday rental instead of a hotel?
If you're looking for a good alternative to a hotel, browse our selection of 39 holiday homes. You can also consider one of the 8 apartments or 9 cottages.

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