Luxury Hotels in Pittsfield, Massachusetts

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Check availability on Pittsfield Luxury Hotels

Tonight
Jul 3 - Jul 4
Tomorrow
Jul 4 - Jul 5
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

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, (1010)
"Great place to stay "
The price is P6,661
P7,441 total
includes taxes & fees
Jul 13 - Jul 14
Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (742)
"Great boutique hotel"
The price is P10,648
P11,893 total
includes taxes & fees
Jul 21 - Jul 22
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, (808)
"Staff was welcoming and informative "
The price is P7,273
P8,124 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
The price is P8,572
P9,575 total
includes taxes & fees
Jul 15 - Jul 16
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 P12,657
P14,138 total
includes taxes & fees
Jul 6 - Jul 7
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 P5,412
P6,045 total
includes taxes & fees
Jul 6 - Jul 7
Berkshire Inn
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (292)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is P6,704
P7,488 total
includes taxes & fees
Jul 28 - Jul 29
The Central Downtown 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, (733)
"Shampoo and toilet paper should have been In the room."
The price is P4,006
P4,474 total
includes taxes & fees
Jul 16 - Jul 17
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 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.