Pittsfield Hotel Guide - Luxury Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Luxury Hotels

Tonight
29 Jun - 30 Jun
Tomorrow
30 Jun - 1 Jul
Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul

Top Pittsfield Luxury Hotels

We don't have any properties that match your exact search

Recommended hotels in Pittsfield

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, (1007)
"Great place to stay "
The price is €104
includes taxes & fees
1 Jul - 2 Jul
Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (742)
"Great boutique hotel"
The price is €180
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (807)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is €117
includes taxes & fees
24 Jul - 25 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is €199
includes taxes & fees
20 Jul - 21 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (635)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is €228
includes taxes & fees
13 Jul - 14 Jul
Hilton Garden Inn Lenox Pittsfield
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (777)
"The motel was nicely done and clean. The beds were comfortable "
The price is €92
includes taxes & fees
1 Jul - 2 Jul
Berkshire Inn
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (289)
"Very nice place to stay. Recently upgraded. Great location and convenient parking."
The price is €123
includes taxes & fees
9 Jul - 10 Jul
The Central Downtown Inn & Suites
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is €964
includes taxes & fees
8 Jul - 9 Jul
Hancock Village Inn at Jiminy Peak
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (731)
"Friendly staff and quick checkin "
The price is €68
includes taxes & fees
13 Jul - 14 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'd like 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 high-end place to stay in Pittsfield?
Yankee Suites Extended Stay is a 4-star guest house with a terrace, and a popular choice for Expedia travellers looking for a luxurious stay.
How many luxury hotels will I be able 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 see more of the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.