The Mahican people originally lived in the area now called Pittsfield, but they moved west in the early 1700s after war and disease decimated their population. A trio of entrepreneurs bought land in the area in the 1730s, intending to subdivide and sell it, but when Native American raids threatened, they abandoned their plans. The township grew organically in the mid-1700s when settlers from Westfield, Massachusetts, moved in.
Pittsfield was officially incorporated in 1761. Its name pays tribute to British politician William Pitt. The introduction of Merino sheep in the early 1800s helped Pittsfield become the country's center of wool manufacturing. Its wool sector was the backbone of Pittsfield's economy for nearly 100 years. The Electric Manufacturing Co., which would later become General Electric, moved to Pittsfield in 1891. It brought more jobs to town, helping Pittsfield's population grow to more than 50,000 by 1930.
Today, Pittsfield's population has dipped to around 44,700, but the locals don't seem to mind. The city is proud of its heritage, its vibrant arts scene, and its status as the “Brooklyn of the Berkshires.”
When should you visit Pittsfield, MA?
Pittsfield's continental climate makes summers a joy, with temperatures only reaching 90 degrees Fahrenheit a handful of times during the season. Many days enjoy average highs in the mid- to high 70s, so this time of year is ideal for sightseeing. However, be prepared to pay extra for your flights and accommodations. While Pittsfield doesn't have the dramatic tourist increases of larger cities, accommodations are limited and providers will charge according to demand.
You can save some money and still enjoy superb weather during the late spring and early fall. The rest of the spring and fall are usually sunny, but bring a coat to protect yourself from a chill in the air.
Pittsfield's cold winters are bitterly cold, with an average of nearly 74 inches of snow falling from December to February every year. If you don't particularly like the cold, you may want to save your sightseeing for the warmer months.
Below is a chart of the current pricing seasonality of hotels and motels in Pittsfield, MA:
Averate Rates by Star Rating
Below are 3 charts displaying average rate trends by star rating class in Pittsfield, MA. Analyze these charts to calculate the least expensive dates to book a room in Pittsfield for any future trips.
Where are the best hotels for luxury in Pittsfield, Maryland?
4 Star Average Prices: $184.40
For a honeymoon or another special getaway, spoil yourself with accommodations at one of Pittsfield's premier hotels. The following establishments celebrate life's luxuries.
Hotel on North in Pittsfield is an elegant boutique hotel where no two guest rooms are quite the same. Each piece of decor has been hand-selected to make your stay special. While the building dates to the 1880s, contemporary additions such as Wi-Fi, smart TVs, and Bluetooth-enabled audio please modern travelers. Unwind with a spa treatment in your room or a board game in the Lounge. Eat on North is the casual but sophisticated on-site restaurant, with former White House chef and local hero Ron Reda at its helm. Its meals showcase sustainable ingredients from Massachusetts, Vermont, and the Hudson Valley.
For a taste of Massachusetts hospitality, stay at White Horse Inn, a sweet boutique bed-and-breakfast in tranquil country surroundings. The rooms feel like home, with premium bedding and cozy fireplaces. Your hosts are welcoming without being overbearing. Their complimentary breakfasts, featuring favorites such as French toast, frittatas, and fresh fruits, are something special. While the White Horse Inn feels a world away from civilization, it's only a short walk from downtown Pittsfield.
What are the most affordable hotels in Pittsfield, MA?
3 Star Average Prices: $176.10
Pittsfield and its surrounding communities have several affordable hotels for travelers on a budget. Enjoy the low rates at the following hotels.
Econo Lodge Pittsfield's affordable rooms are simple but functional, with air conditioning units, coffeemakers, work desks, and flat-screen TVs for lazy nights in your room. It's ideal for budget-friendly extended stays, with an on-site guest laundry and fitness center. Copy and fax services and a small meeting room also make Econo Lodge Pittsfield a good choice for business travel. Help yourself to the free continental breakfast, including pastries and make-your-own waffles, each morning. It's easy to stay up-to-date, with weekday newspapers and Wi-Fi both included in the low room rate.
Days Inn by Wyndham Lenox is a few miles from downtown Pittsfield in Lenox, but its outdoor pool makes it worth the drive for summer travelers. This charming hotel's rooms also offer style for the money, with plush bedding, large 39-inch flat-screen TVs, microwave ovens, and refrigerators. Road trippers will appreciate the free parking, which is large enough to accommodate RVs. The free continental Daybreak breakfast will help you get moving in the morning.
2 Star Average Prices: $153.37
What hotels have the best discounted rates in Pittsfield, MA?
Members of leading hotel groups often discount their rates for special travelers. You could stand to save a significant amount of money at the following Pittsfield establishments.
Independent (SPHC) Berkshire Plaza Hotel, formerly the Crown Plaza Pittsfield-Berkshires, treats AAA and CAA auto club members, Entertainment Card holders, U.S. and Canadian government employees (including U.S. state government workers), and seniors to generous discounts. You'll love the facilities, including a heated indoor pool, Jacuzzi, sauna, and fitness center. When you're keeping fit, you can afford to indulge in the hotel's One West Restaurant, cocktail lounge, or lively sports bar. The rooms are chic and well-appointed, with complimentary Wi-Fi, flat-screen TVs, and plush beds. Request a room in a Quiet Zone for the best night's sleep.
Hilton Garden Inn Lenox Pittsfield has special rates for AAA auto club members, seniors and AARP members, government and military personnel, and travel agents. This full-featured hotel has beautiful guest rooms with high-definition TVs, ergonomic work zones, coffee- and tea-making facilities, and Serta beds for the best night's sleep. The Garden Grille & Bar serves a lavish buffet each morning and American favorites for dinner. Guests love the heated indoor pool, fitness center, and soothing hot tub.
Where are the hotels with the most value near Pittsfield?
Extend the value of your stay at the following Pittsfield hotels offering great facilities and plenty of benefits.
Yankee Suites Extended Stay is set up for extended getaways, so it offers all the comforts of home. You can save money by using your in-room kitchen and eating in. The hotel also has its own coin laundry so that you can catch up on your washing. You won't find sneaky surcharges for Wi-Fi, and parking is also free at a nearby secure location. Special weekly and monthly rates can also help you save money at the Yankee Suites Extended Stay.
The Berkshire Inn is a friendly family-owned and operated hotel nestled in the tranquil Berkshire Mountains. Its elegant rooms feature either a single king bed or pair of queens, along with air conditioning, flat-screen TVs, microwaves, and refrigerators. Internet access is free throughout the hotel, as is the seasonal continental breakfast. You'll love the outdoor pool during summer and the inn's easy access to the Berkshires.
What should you do while visiting Pittsfield, MA?
For a small city, Pittsfield punches above its weight with a host of arts attractions and regular cultural events. Culture vultures shouldn't miss the following attractions while they're in town.
Downtown Pittsfield is like a large outdoor gallery full of amazing sculptures to delight passers-by. These colorful works were created by some of the country's leading artists including Ze'ev Willy Neumann and Jack Howard-Potter. See them all on the ArtScape self-guided tour.
Downtown Pittsfield also has the Colonial Theater, which dates to 1903. Over $22 million in renovations helped restore this theater, one of the only remaining from the Vaudeville era, to its former glory. Luminaries such as John Barrymore, Douglas Fairbanks Sr., and John Philip Sousa have all graced its stage. Today, the Colonial Theater continues its rich tradition, hosting musical and theatrical performances. The Berkshire Theatre Group regularly stages plays and musicals at the Colonial Theater.
Albany Berkshire Ballet is also based in Pittsfield. This professional company stages classical and contemporary dance productions at the Colonial Theater and around the country. Co-productions with the Albany Symphony Orchestra are unmissable.
Barrington Stage Company, which developed the Tony Award-winning "The 25th Annual Putnam County Spelling Bee," is proudly based in Pittsfield. This dynamic theater company stages its works at the Boyd-Quinson Mainstage, Mr. Finn's Cabaret, and the St. Germain Stage. It also has a youth theater division which offers family-friendly productions.
The Berkshire Museum is a large arts and natural history museum with a rich history dating back to 1903. Its collections of Ancient Egyptian and Babylonian art are particularly impressive, but modern works from celebrated artists exist here, including Thomas Dewing, Robert Reid, Gregory Crewdson, and Peter Garfield. Traveling exhibitions help complement the museum's permanent collection. You can also see the best of independent and foreign film at the museum's Little Cinema every week.
Pittsfield is a small city that's big on charm. Whether you love sightseeing or you're simply looking to escape the hustle and bustle of your everyday routine, Pittsfield makes the ideal travel destination.
FAQs about hotels in Pittsfield
How much does a cheap hotel in Pittsfield cost per night?
In the last year, a 2 star hotel in Pittsfield can be as cheap as $153.37 per night. (based on HotelPlanner prices)
How much does a 3 star hotel in Pittsfield cost per night?
In the last year, the average 3 star hotel in Pittsfield has been $176.10 per night. (based on HotelPlanner prices)
How much does a luxury hotel in Pittsfield cost?
In the last year, the average 4 star hotel in Pittsfield has been $184.40 per night. (based on HotelPlanner prices)
Recent traveler guest reviews of Pittsfield, MA
Below are reviews of the city of Pittsfield, MA from an actual visitor's perspective.
"Easy to navigate around the city"
Score
5.0 / 5
Kathleen S., from 24-Sep-2026
"Convenient location from Tanglewood"
Score
5.0 / 5
Michele M., from 17-Sep-2026
"I love Pittsfield"
Score
5.0 / 5
I love Pittsfield, my hometown, and always home in my heart.
Mary G., from 24-Jul-2026
"Easy to walk around"
Score
4.0 / 5
Martha S., from 23-Jul-2026
"Easy to visit"
Score
4.0 / 5
Martha S., from 23-Jul-2026
"Near Tanglewood"
Score
5.0 / 5
Good proximity to Tanglewood.
John H., from 07-Jul-2026
"Tanglewood"
Score
5.0 / 5
Michael L., from 07-Jul-2026
"Pittsfield has good theater"
Score
5.0 / 5
Pittsfield has good theater, good restaurants, is less crowded than Lenox and close to all the Berkshires offers.
Ruth S., from 31-May-2026
"I grew up in Berkshire County"
Score
5.0 / 5
I grew up in Berkshire County, it is home.
Richard M., from 10-Oct-2025
"I love Pittsfield"
Score
5.0 / 5
Thomas T., from 14-Sep-2025
"Good Location"
Score
4.0 / 5
The hotel was just 15 minutes from Tanglewood so it was it was a convenient location as we attended both a Saturday night concert and a Sunday afternoon concert at Tanglewood.
Joyce D., from 26-Aug-2025
"Great Location"
Score
5.0 / 5
Was able to have dinner across the street Great location to Tanglewood
Gail W., from 19-Aug-2025
"Exciting Drag Racing!"
Score
5.0 / 5
The nearby dirt track racing and a 1/4 mile dragstrip in Lebanon made for a exciting afternoon/evening.
Michael B., from 06-Jul-2025
"Beautiful Area"
Score
5.0 / 5
I grew up in Lenox & Pittsfield and live in California and I love visiting Family primarily but also so many beautiful places in the Berkshires especially in the Fall.
Patricia K., from 25-Oct-2024
"Pleasant Community"
Score
4.0 / 5
Pleasant community.
Gerard V., from 19-Mar-2024
"Love Barrington Stage!"
Score
5.0 / 5
Love Barrington Stage!
Michael M., from 13-Mar-2024
"Berkshire Botanical Gardens, Norman Rockwell Museum & Edith Wharton Grounds"
Score
4.0 / 5
Nice views. We visited Berkshire Botanical Gardens, Norman Rockwell Museum and Edith Wharton Grounds. We'll have to come back for the house tour.
Susan M., from 01-May-2023
"In the heart of the Berkshires!"
Score
5.0 / 5
In the heart of the Berkshires, so much to do! Even has a museum associated with the Smithsonian!
Lisa K., from 21-Mar-2023
"Quality Atmosphere!"
Score
5.0 / 5
Small unpretentious Berkshires community with quality atmosphere!
Richard S., from 16-Nov-2022
"Located across from a gym."
Score
5.0 / 5
Gym across the street
William H., from 08-Nov-2022
"Mount Greylock & Beautiful Views!"
Score
5.0 / 5
Love the Berkshire Museum…. Quirky!
Drove to top of Mt. Greylock… beautiful views.
Patrick's Pub is a great restaurant nearby and we didn't have to make reservations 😊
All in all a very good experience…thanks!
Fran R., from 13-Oct-2022
"The Berkshires are beautiful this time of year!"
Score
5.0 / 5
The Berkshires are beautiful this time of year, and I didn't spend a lot of time in the room.
John H., from 06-Sep-2022
"Conveniently Located"
Score
4.0 / 5
Convenient; been here many times.
Charles N., from 02-Aug-2022
"Beautiful area with lots to do!"
Score
5.0 / 5
Beautiful area with lots to do.
Melvyn Y., from 07-Jul-2022
"Nice!"
Score
4.0 / 5
Nice!
Contina G., from 13-Dec-2021
"Nice People"
Score
5.0 / 5
The people of Pittsfield are warm and friendly.
Maria P., from 14-Jun-2014
The average traveler rating of the city of Pittsfield, MA shown above is
4.7 out of 5 based on 26 reviews