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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 5167 reviews
Honeysuckle Rose Cottage
4 guests · 2 bedrooms · 2 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$86 / night
Entire apartment
Rating 4.80 out of 5225 reviews
Contemporary Berkshires Getaway
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$79 / night
SUPERHOST
Entire apartment
Rating 4.80 out of 550 reviews
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests · 2 bedrooms · 2 beds · 1.5 baths
Wi-Fi · Kitchen · Heating
Price:$67 / night
Entire house
Rating 4.87 out of 515 reviews
Dancing Horse Lodge
6 guests · 3 bedrooms · 3 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$71 / night
SUPERHOST
Entire apartment
Rating 4.66 out of 556 reviews
Sharon's Place 4 ..... pets, and 420 friendly!!!!
2 guests · Studio · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$43 / night
SUPERHOST
Entire apartment
Rating 4.85 out of 559 reviews
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests · 1 bedroom · 2 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$59 / night
SUPERHOST
Entire cottage
Rating 5.0 out of 517 reviews
Magical round cottage in the woods
4 guests · 2 bedrooms · 2 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$64 / night
SUPERHOST
Entire guest suite
Rating 4.92 out of 539 reviews
Berkshire Guest Suite
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Heating
Price:$56 / night
SUPERHOST
Entire apartment
Rating 4.95 out of 566 reviews
Heart Of The Berkshires
5 guests · 3 bedrooms · 3 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$72 / night
SUPERHOST
Entire apartment
Rating 4.88 out of 592 reviews
Marie's Place
4 guests · 2 bedrooms · 2 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$82 / night
SUPERHOST
Entire apartment
Rating 5.0 out of 515 reviews
Simply off North
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$83 / night
SUPERHOST
Entire house
Rating 4.97 out of 536 reviews
Spacious Duplex in Heart of the Berkshires
4 guests · 2 bedrooms · 2 beds · 1.5 baths
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$90 / night
Entire cottage
Rating 4.67 out of 53 reviews
The Sail Loft
4 guests · 1 bedroom · 2 beds · 1.5 baths
Wi-Fi · Kitchen · Heating
Price:$55 / night
SUPERHOST
Entire apartment
Rating 5.0 out of 56 reviews
Just off North
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$95 / night
SUPERHOST
Entire apartment
Rating 4.85 out of 527 reviews
Downtown Apartment
4 guests · 2 bedrooms · 3 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$119 / night
Entire apartment
Rating 4.60 out of 559 reviews
The Guests House, Pet Friendly, Central, Near Lake
5 guests · 2 bedrooms · 3 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$99 / night
Entire house
Rating 4.85 out of 513 reviews
Berkshire beautiful one floor house
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$136 / night
Entire apartment
Rating 4.61 out of 5175 reviews
Cozy Suite with huge bar and stone fireplace!
4 guests · Studio · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$59 / night
1 18 of 300+ Rentals
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