Find Boutique Hotels in Pittsfield, MA

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Check availability on Pittsfield Boutique Hotels

Tonight
Aug 3 - Aug 4
Tomorrow
Aug 4 - Aug 5
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Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Pittsfield Boutique Hotels

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

Recommended hotels in Pittsfield

Huttopia Berkshires
Deluxe Tent | 2 bedrooms

Huttopia Berkshires

1.0 star property
The price is NT$2,937
NT$3,281 total
includes taxes & fees
Sep 1 - Sep 2
Huttopia Berkshires
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1004)
"Property was very nice clean rooms "
The price is NT$2,777
NT$3,102 total
includes taxes & fees
Sep 2 - Sep 3
Quality Inn
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)
"Very nice stay"
The price is NT$3,566
NT$3,984 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (7)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NT$4,815
NT$5,379 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires
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, (843)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is NT$3,447
NT$3,850 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (538)
"Excellent stay!"
The price is NT$2,843
NT$3,846 total
includes taxes & fees
Sep 2 - Sep 3
Berkshire Mountain Lodge
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (749)
"Staff were excellent and welcoming."
The price is NT$5,665
NT$6,328 total
includes taxes & fees
Aug 5 - Aug 6
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, (789)
"It was a good place to sleep for a quick visit to Pittsfield. Glad we booked there. "
The price is NT$2,997
NT$3,348 total
includes taxes & fees
Aug 4 - Aug 5
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"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 NT$4,762
NT$5,319 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Garden Inn Lenox Pittsfield
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.

Top Pittsfield Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"This hotel has a lot more character than chain places on the highway, and parking was easy in the lot behind the hotel. Staff was friendly and efficient, the rooms were large and well-decorated, and the restaurant on the ground floor was top-notch."
Hugh 1-night trip
Posted 2 days ago
Hotel On North

Frequently asked questions

What's the best boutique-style hotel in Pittsfield?
Hotel On North is a favorite 3.5-star hotel with our travelers looking for a stylish accommodation, featuring 45 guestrooms, a restaurant, and a bar.
What's there to see and do in Pittsfield?
The theaters 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 you plan your trip. 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 the best way to get to my boutique hotel in Pittsfield?
You have a few options for getting to 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.