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Over 3,300 guest reviews for places to stay in Pittsfield, with an average of 4.9 out of 5 stars.

300+ places to stay

Entire house
Rating 4.80 out of 5177 reviews
Honeysuckle Rose Cottage
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Heating · Kitchen
Price:$86 / night
SUPERHOST
Private room
Rating 4.73 out of 530 reviews
Sharon`s place 1
2 guests · 1 bedroom · 1 bed · 1 shared bath
Wifi · Kitchen
Price:$15 / night
SUPERHOST
Entire apartment
Rating 4.70 out of 563 reviews
Sharon's Place 4 ..... pets, and 420 friendly!!!!
2 guests · Studio · 1 bed · 1 bath
Wifi · Heating · Kitchen
Price:$43 / night
SUPERHOST
Entire apartment
Rating 4.80 out of 555 reviews
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests · 2 bedrooms · 2 beds · 1.5 baths
Wifi · Heating · Kitchen
Price:$67 / night
Entire apartment
Rating 4.81 out of 5229 reviews
Contemporary Berkshires Getaway
2 guests · 1 bedroom · 1 bed · 1 bath
Wifi · Heating · Kitchen
Price:$79 / night
SUPERHOST
Entire house
Rating 4.98 out of 543 reviews
Spacious Duplex in Heart of the Berkshires
4 guests · 2 bedrooms · 2 beds · 1.5 baths
Wifi · Indoor fireplace · Heating · Kitchen
Price:$110 / night
SUPERHOST
Entire apartment
Rating 4.81 out of 564 reviews
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Heating · Kitchen
Price:$59 / night
Entire house
Rating 4.91 out of 522 reviews
Dancing Horse Lodge
6 guests · 3 bedrooms · 3 beds · 1 bath
Wifi · Heating · Kitchen
Price:$71 / night
SUPERHOST
Private room
Rating 5.0 out of 513 reviews
Private Room and Bathroom - Clean and Spacious
2 guests · 1 bedroom · 1 bed · 1.5 baths
Wifi · Heating · Kitchen
Price:$48 / night
Private room
Rating 4.99 out of 597 reviews
Queen Room w/Private Bath in Quiet Berkshires Home
2 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Heating
Price:$60 / night
Entire house
Rating 4.77 out of 569 reviews
Big Beautiful House By The Lake W/Jetted Hot Tub
16+ guests · 8 bedrooms · 11 beds · 3 baths
Wifi · Heating · Kitchen
Price:$325 / night
Entire apartment
1BR Oasis at Vacation Village in the Berkshires
4 guests · 1 bedroom · 2 beds · 1 bath
Wifi · Indoor fireplace · Heating · Kitchen
Price:$50 / night
SUPERHOST
Private room
Rating 4.97 out of 560 reviews
Spacious bedroom with private bath in Dalton, MA
3 guests · 1 bedroom · 2 beds · 1 private bath
Wifi · Heating
Price:$60 / night
SUPERHOST
Entire apartment
Rating 4.88 out of 598 reviews
Marie's Place
4 guests · 2 bedrooms · 2 beds · 1 bath
Wifi · Heating · Kitchen
Price:$79 / night
SUPERHOST
Entire apartment
Rating 4.87 out of 530 reviews
Downtown Apartment B
4 guests · 2 bedrooms · 3 beds · 1 bath
Wifi · Heating · Kitchen
Price:$99 / night
SUPERHOST
Private room
Rating 5.0 out of 57 reviews
Modern, Spacious Master Bedroom and Bathroom
2 guests · 1 bedroom · 1 bed · 1.5 baths
Wifi · Heating · Kitchen
Price:$51 / night
Private room
Rating 4.34 out of 571 reviews
Private room / bath ctr Berkshires
2 guests · 1 bedroom · 1 bed · 1 private bath
Wifi · Heating · Kitchen
Price:$39 / night
Entire cottage
Rating 4.88 out of 58 reviews
The Sail Loft
4 guests · 1 bedroom · 2 beds · 1.5 baths
Wifi · Heating · Kitchen
Price:$79 / night
1 18 of 300+ places to stay
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