Pittsfield Hotel Guide - Boutique Hotels in Pittsfield, Massachusetts

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Top Pittsfield Boutique Hotels

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Recommended hotels in Pittsfield

Holiday Inn Express & Suites Pittsfield - Berkshires
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (2)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is €130
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
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 €113
includes taxes & fees
13 Jul - 14 Jul
Best Western Plus Berkshire Hills Inn & Suites
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, (816)
"Very convenient location, downtown, short drive to local attractions "
The price is €110
includes taxes & fees
13 Jul - 14 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (506)
"We enjoyed our stay here. It was very quiet, and had everything we needed."
Berkshire Mountain Lodge
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is €180
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (779)
"The motel was nicely done and clean. The beds were comfortable "
The price is €95
includes taxes & fees
10 Jul - 11 Jul
Berkshire Inn
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Smart TV

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is €179
includes taxes & fees
15 Jul - 16 Jul
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (636)
"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 €214
includes taxes & fees
13 Jul - 14 Jul
Hilton Garden Inn Lenox Pittsfield
The Central Downtown Inn & Suites
Microwave, oven, stovetop, dishwasher

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (295)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is €113
includes taxes & fees
14 Jul - 15 Jul
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, (738)
"A total dump !"
The price is €68
includes taxes & fees
22 Jul - 23 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

What's the best boutique-style accommodation in Pittsfield?
Hotel On North is a favourite 3.5-star hotel with our travellers looking for stylish accommodation, and features 45 guestrooms, a restaurant and a bar.
What's there to see and do in Pittsfield?
The theatres and sporting events are just some of the things to enjoy while you're in the area. Experience the cultural highlights around Pittsfield with a visit to Berkshire Museum, Colonial Theater and Barrington Stage Company. You might also like to explore more of the area and take in additional sights like Bousquet Ski Area, Hancock Shaker Village and Herman Melville's Arrowhead while you're here.
What kind of weather should I plan for when I travel to Pittsfield?
Getting an idea of what to expect from the weather in Pittsfield is important when planning your trip. 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 the best way to get to my boutique hotel in Pittsfield?
You have a few options for transportation to and around Pittsfield. The closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city, but Hudson, NY (HCC-Columbia County) may also be an option. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.