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

23 places to stay

SUPERHOST
Farm stay
Sheep Barn on the Greylock Valley Estate
6 guests3 bedrooms3 beds2 baths
WifiKitchenHeatingIndoor fireplace
Price:$90 / night
Private room
A Stay at the Homestead
2 guests1 bedroom1 bed2 shared baths
WifiHeatingIndoor fireplace
Includes cancellation flexibility
Price:$39 / night
SUPERHOST
Camper/RV
Cozy Private Tiny House Trailer
2 guests1 bedroom1 bed1 bath
WifiKitchenHeating
Price:$45 / night
Private room
Equestrian retreat
4 guests2 bedrooms2 beds1 bath
WifiHeatingIndoor fireplace
Includes cancellation flexibility
Price:$95 / night
Tent
Tentrr - Berkshire Mountain Hideaway
4 guests1 bedroom2 beds1 bath
Heating
Includes cancellation flexibility
Price:$120 / night
SUPERHOST
Farm stay
Shadowbrook Farm Stay
6 guests2 bedrooms3 beds1 bath
WifiKitchenHeatingIndoor fireplace
Includes cancellation flexibility
Price:$250 / night
Tent
Tentrr - Birch Berry Pines
4 guests1 bedroom1 bed1 bath
Indoor fireplace
Includes cancellation flexibility
Price:$100 / night
Private room
Farmhouse Suite on Berkshire Farm
2 guests1 bedroom1 bed1 private bath
Heating
Includes cancellation flexibility
Price:$75 / night
Camper/RV
"Glamping" in the Berkshires! 🌿🌳🌲
6 guests2 bedrooms5 beds1 bath
WifiKitchenHeating
Price:$119 / night
Tent
Tentrr - Running Spring Farm
6 guests1 bedroom2 beds1 bath
Heating
Includes cancellation flexibility
Price:$110 / night
Camper/RV
Vintage Camper on Berkshire Farm
3 guests1 bedroom2 beds1 bath
Kitchen
Includes cancellation flexibility
Price:$65 / night
Tent
Tentrr - Hilltop Nook Berkshires
6 guests1 bedroom2 beds1 bath
Heating
Includes cancellation flexibility
Price:$120 / night
Tent
Tentrr - Round Mountain Campsite
6 guests1 bedroom2 beds1 bath
Heating
Includes cancellation flexibility
Price:$115 / night
SUPERHOST
Private room
Sweet Queen Bedroom on Small Farm
2 guests1 bedroom1 bed1 private bath
WifiKitchenHeatingIndoor fireplace
Includes cancellation flexibility
Price:$75 / night
Tent
Tentrr - Living Water Campsites: Ski N' Zip 2
4 guests1 bedroom1 bed1 bath
Heating
Includes cancellation flexibility
Price:$119 / night
Tent
Tentrr - Center Berlin Campsite
4 guests1 bedroom1 bed1 bath
Heating
Includes cancellation flexibility
Price:$115 / night
Farm stay
James + Hudson Farm
16+ guests6 bedrooms11 beds5.5 baths
WifiKitchenHeatingIndoor fireplace
Includes cancellation flexibility
Price:$3,500 / night
Tent
Tentrr - Living Water Campsites: Mossy Acres 1
4 guests1 bedroom1 bed1 bath
Heating
Includes cancellation flexibility
Price:$119 / night
SUPERHOST
Barn
Tranquility Barn - Hudson/Chatham/Berkshires area
9 guests2 bedrooms9 beds3 baths
WifiKitchenHeatingIndoor fireplace
Includes cancellation flexibility
Price:$345 / night
Tent
Tentrr - Living Water Campsites: Ski N' Zip 1
4 guests1 bedroom1 bed1 bath
Heating
Includes cancellation flexibility
Price:$119 / night
1 20 of 23 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.