Find Luxury Hotels in Pittsfield, MA

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Check availability on Pittsfield Luxury Hotels

Tonight
23 Feb - 24 Feb
Tomorrow
24 Feb - 25 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

Compare Pittsfield Luxury Hotels 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, (683)
"Amazing place to stay. So unique and cozy! I would stay there everytime l visited Pittsfield but its always booked because its so popular."
The price is AED 400
AED 447 total
includes taxes & fees
2 Mar - 3 Mar
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (738)
"Great for the money. Unfortunately the jacuzzi was non-functional which was the one thing I was looking forward to after a ski day. Hotel staff was amazing."
The price is AED 382
AED 427 total
includes taxes & fees
28 Feb - 1 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Exterior

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (272)
"The suite we stayed in was spacious. Maid service is only once weekly, but when we contacted them about getting additional toilet paper, they were very responsive. The queen bed in the bedroom was very comfortable. We were not able to get the TV in the bedroom to work. The sofa queen bed in the living room was all broken down. My husband had to put boards under the mattress to support it enough so he could use the bed. The kitchen was clean and well-stocked."
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Exterior

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"Property isn’t pet friendly, it’s dog friendly. We use Expedia for all our bookings but told by hotel the policy is more restrictive than Expedia indicates. Best Western shouldn’t accept reservations from Expedia that don’t conform to your actual policy. The manager was kind enough to work it out for us but it would be better for all to put the burden on the business offering service, not the consumer trying to make the best choice for their needs. "
The price is AED 368
AED 411 total
includes taxes & fees
24 Feb - 25 Feb
Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express
Room

FairBridge Inn Express

2.5 star property
5.4 out of 10, (704)
"Quiet "
The price is AED 228
AED 255 total
includes taxes & fees
8 Mar - 9 Mar
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.