Find Luxury Hotels in Pittsfield, MA

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Pick from 6 Pittsfield Luxury Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Hotel On North
Front of property - evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (645)
"Fun decor and comfy beds. Lovely bathroom. Highly recommend."
The price is SAR 545
SAR 608 total
includes taxes & fees
14 Nov - 15 Nov
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Exterior
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (670)
"My stay at the Holiday Inn was very pleasant!"
The price is SAR 353
SAR 394 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Central Downtown Inn & Suites
Exterior
The Central Downtown Inn & Suites
4.0 star property
8.8 out of 10, Excellent, (267)
"I loved all the amenities and space provided in the suite. And it was very affordable. It was like staying in an apartment. It was very clean. The bedroom wall was thin though because I could hear snoring on the other side. Pretty view of the trees in the backyard."
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very Good, (1000)
"Staff was extremely friendly and helpful!! Anything we needed they had options for us. AAA !"
The price is SAR 382
SAR 427 total
includes taxes & fees
13 Nov - 14 Nov
Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express
Room
FairBridge Inn Express
2.5 star property
5.4 out of 10, (676)
"I don’t know so many complaints. Bed was good, clean. Plenty of park. Provided what we paid for and was expecting. "
The price is SAR 297
SAR 331 total
includes taxes & fees
13 Nov - 14 Nov
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.
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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 need 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.
How many luxury hotels should I expect 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 temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches 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 Bousquet Ski Area. If you have spare time during your trip, you might want to make a stop at Pittsfield State Forest 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 venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.