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Check availability on Pittsfield Luxury Hotels

Top Luxury Hotels in Pittsfield

Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"If you are ever in Pittsfield, Massachusetts, stay here!!! I had a room on the second floor facing North Street. It was
luxurious
, yet unpretentious, absolutely comfortable, I wanted to move in. The second floor area outside the room is a glorious wide space with a table, sitting area, and books and board games on a shelf. I've included photos. The front desk staff was friendly, informative, and efficient. I had lots of questions and they answered them all. The restaurant in the lobby, which...
Scott
The price is S$270
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (818)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
Helen
The price is S$184
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (296)
"Cleanliness and comfort ranked very high here. We very much enjoyed the comfortable, large king bed and the cushy living room sofa. The unit was the size of a small apartment with large rooms having lots of windows and light including a large balcony with chairs - views of green leafy trees from some windows and town views from others (such as a parking lot etc. but expected being in downtown). It has a kitchen with all of the standard large and basic small appliances and all were clean and in...
Angela
The price is S$184
includes taxes & fees
15 Jul - 16 Jul
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1011)
"Friendly staff, fast check-in, Room was comfortable, water in tub took time to warm up but fluffy towels evened out. Very good hot breakfast with a really helpful breakfast attendant. Would stay here again."
Richard
The price is S$156
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (739)
"Bed was too hard, but chairs were comfortable. Nice shower, good hot water."
Anonymous traveller
The price is S$102
includes taxes & fees
27 Jul - 28 Jul
FairBridge Inn Express
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.

Frequently asked questions

Are you looking for a luxury hotel for your stay in Pittsfield?
Use Expedia to arrange your flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay special. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Pittsfield has to offer. While you're visiting, you might want to think about enjoying the entertainment and sporting events, which Pittsfield is known for.
What's the best high-end place to stay in Pittsfield?
Yankee Suites Extended Stay is a 4-star guest house with a terrace, and a popular choice for Expedia travellers looking for a luxurious stay.
How many luxury hotels will I be able to find in Pittsfield?
Lie in the lap of luxury during your getaway to Pittsfield in one of Expedia's 8 luxury hotels.
When can I expect good weather in Pittsfield?
Planning for the weather is an important factor for making your trip to Pittsfield a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What's there to see and do in Pittsfield?
Enjoy all that Pittsfield has to offer when you visit Berkshire Museum, Colonial Theater and Barrington Stage Company. If you have spare time during your trip, you might want to make a stop at Bousquet Ski Area and Hancock Shaker Village.
How can I get around Pittsfield?
It's easier to get around town in style when you know your options. To see more of the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.