Luxury Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Luxury Hotels

Tonight
Jul 19 - Jul 20
Tomorrow
Jul 20 - Jul 21
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Top Pittsfield Luxury Hotels

Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (744)
"Great boutique hotel"
The price is P10,809
P12,074 total
includes taxes & fees
Aug 4 - Aug 5
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (824)
"Very convenient location, downtown, short drive to local attractions "
The price is P7,492
P8,369 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is P7,378
P8,241 total
includes taxes & fees
Jul 21 - Jul 22
The Central Downtown Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
Welcome to our reception area, featuring a comfortable seating area, a reception desk, and a beautiful abstract art piece.

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1010)
"Very nice stay"
The price is P7,243
P8,091 total
includes taxes & fees
Jul 30 - Jul 31
Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (744)
"Close to our target event a plus"
The price is P4,066
P4,542 total
includes taxes & fees
Aug 3 - Aug 4
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 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.
What's the best luxury accommodation in Pittsfield?
Yankee Suites Extended Stay is a 4-star guesthouse with a terrace, and a popular choice for Expedia travelers looking for a luxurious stay.
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 Barrington Stage Company. If you have spare time during your trip, you might want to make a stop at Herman Melville's Arrowhead and Bousquet Ski Area.
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.