Find Luxury Hotels in Pittsfield, MA

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Luxury Hotels

Tonight
Jan 4 - Jan 5
Tomorrow
Jan 5 - Jan 6
Next weekend
Jan 9 - Jan 11
In two weeks
Jan 16 - Jan 18

Our top choices for Pittsfield luxury hotels

Front of property - evening/night
Hotel On North

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (811)
"Clean room and staff was super friendly"
United States
Yuen
The price is NT$4,680
NT$5,228 total
includes taxes & fees
Jan 7 - Jan 8
Hotel On North
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1006)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NT$3,078
NT$3,438 total
includes taxes & fees
Jan 9 - Jan 10
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Microwave, oven, stovetop, dishwasher
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (351)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is NT$2,953
NT$3,298 total
includes taxes & fees
Jan 5 - Jan 6
The Central Downtown Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1002)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,399
NT$2,680 total
includes taxes & fees
Jan 11 - Jan 12
Best Western Plus Berkshire Hills Inn & Suites
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (811)
"Room spotless and staff helpful."
United States
William
The price is NT$2,516
NT$2,810 total
includes taxes & fees
Jan 18 - Jan 19
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.
View all properties

Top Pittsfield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room was cozy and clean. Loved the fireplace & view. Great price too. Cameron at the front desk was pleasant and working hard the several times we saw him. Pool was warm & hot tub was nice! Overall, great stay! Will definitely stay again! "
Kimberly 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

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.
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 Hancock Shaker Village and Housatonic River.
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.

Explore a world of travel with Expedia