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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.

24 places to stay

SUPERHOST
Tiny house
Rating 5.0 out of 510 reviews
Tiny cabin in the woods
2 guests · Studio · 0 beds · Half-bath
Price:$70 / night
SUPERHOST
Farm stay
Rating 4.92 out of 537 reviews
Shadowbrook Farm Stay
6 guests · 2 bedrooms · 3 beds · 1 bath
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$250 / night
Camper/RV
Rating 4.88 out of 58 reviews
Vintage Camper on Berkshire Farm
3 guests · 1 bedroom · 2 beds · 1 bath
Kitchen
Price:$65 / night
SUPERHOST
Camper/RV
Rating 4.89 out of 571 reviews
Cozy Private Tiny House Trailer
2 guests · 1 bedroom · 1 bed · 1 bath
Wi-Fi · Kitchen · Heating
Price:$45 / night
Camper/RV
Rating 5.0 out of 54 reviews
"Glamping" in the Berkshires! 🌿🌳🌲
6 guests · 2 bedrooms · 5 beds · 1 bath
Wi-Fi · Kitchen · Heating
Price:$119 / night
Tent
Rating 5.0 out of 53 reviews
Tentrr - Living Water Campsites: Ski N' Zip 2
4 guests · 1 bedroom · 1 bed · 1 bath
Heating
Price:$104 / night
SUPERHOST
Farm stay
Rating 4.79 out of 573 reviews
Sheep Barn on the Greylock Valley Estate
6 guests · 3 bedrooms · 3 beds · 2 baths
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$185 / night
Private room
Rating 4.94 out of 547 reviews
Sweet Queen Bedroom on Small Farm
2 guests · 1 bedroom · 1 bed · 1 private bath
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$75 / night
Tent
Rating 5.0 out of 53 reviews
Tentrr - Berkshire Mountain Hideaway
4 guests · 1 bedroom · 2 beds · 1 bath
Indoor fireplace
Price:$115 / night
Private room
Rating 4.96 out of 578 reviews
Farmhouse Suite on Berkshire Farm
2 guests · 1 bedroom · 1 bed · 1 private bath
Heating
Price:$75 / night
Tent
Tentrr - Birch Berry Pines
4 guests · 1 bedroom · 1 bed · 1 bath
Indoor fireplace
Price:$115 / night
Tent
Tentrr - Running Spring Farm
6 guests · 1 bedroom · 2 beds · 1 bath
Heating
Price:$115 / night
SUPERHOST
Barn
Rating 5.0 out of 528 reviews
Tranquility Barn - Hudson/Chatham/Berkshires area
9 guests · 2 bedrooms · 9 beds · 3 baths
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$345 / night
SUPERHOST
Barn
Rating 4.94 out of 580 reviews
Lovely Barn Loft in Heart Of Berkshires
4 guests · Studio · 2 beds · 1 bath
Wi-Fi · Kitchen · Heating · Indoor fireplace
Price:$119 / night
Tent
Tentrr - Berkshire Magic Woods
4 guests · 1 bedroom · 1 bed · 1 bath
Heating
Price:$120 / night
Tent
Tentrr - Living Water Campsites: Mossy Acres 1
4 guests · 1 bedroom · 1 bed · 1 bath
Heating
Price:$104 / night
Tent
Tentrr - Hilltop Nook Berkshires
6 guests · 1 bedroom · 2 beds · 1 bath
Heating
Price:$130 / night
Tent
Tentrr - Round Mountain Campsite
6 guests · 1 bedroom · 2 beds · 1 bath
Heating
Price:$115 / night
1 18 of 24 Rentals
Enter dates to see full pricing. Additional fees apply. Taxes may be added. Free cancellation only applicable within 48 hours from booking.