Find Luxury Hotels in Pittsfield, MA

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check availability on Pittsfield Luxury Hotels

Tonight
21 Jun - 22 Jun
Tomorrow
22 Jun - 23 Jun
Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul

Top Pittsfield Luxury Hotels

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (736)
"Best hotel in the Berkshire! "
The price is SAR 563
SAR 629 total
includes taxes & fees
30 Jun - 1 Jul
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, (795)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is SAR 409
SAR 457 total
includes taxes & fees
26 Jun - 27 Jun
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, (287)
"Very nice place to stay. Recently upgraded. Great location and convenient parking."
The price is SAR 484
SAR 541 total
includes taxes & fees
29 Jun - 30 Jun
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, (1001)
"Great place to stay "
The price is SAR 380
SAR 424 total
includes taxes & fees
1 Jul - 2 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, (726)
"Friendly staff and quick checkin "
The price is SAR 267
SAR 298 total
includes taxes & fees
6 Jul - 7 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 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 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 venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.