141 stays

Stays in Pittsfield

Enter dates and number of guests to see the total price per night.
Review COVID-19 travel restrictions before you book.
Learn more
Entire rental unit in Pittsfield
Lovely 1-Bedroom Apartment Rental with Parking
4 guests1 bedroom1 bed1 bath
WifiKitchenFree parkingAir conditioning
Private room in Pittsfield
Sharon's place 12
2 guests1 bedroom1 bed1 shared bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire rental unit in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire residential home in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parkingAir conditioning
Entire rental unit in Pittsfield
Sharon's Place 4 .....420 friendly!!!!
2 guestsStudio1 bed1 bath
WifiKitchenFree parkingAir conditioning
Entire rental unit in Pittsfield
The sweet place in the beautiful Berkshires!
5 guests2 bedrooms3 beds1 bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire rental unit in Pittsfield
Just off North
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire residential home in Pittsfield
Dancing Horse Lodge
6 guests3 bedrooms3 beds1 bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire residential home in Dalton
The Yellow House
3 guests1 bedroom2 beds1 bath
WifiKitchenFree parking
Entire rental unit in Pittsfield
Lovely Apartment in Historic Berkshire Victorian 1
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parkingAir conditioning
Entire rental unit in Pittsfield
Sharon's Place 5 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bath
WifiKitchenFree parkingAir conditioning
Entire rental unit in Pittsfield
Charming Apartment In Berkshire Victorian Home
8 guests3 bedrooms5 beds1.5 baths
WifiKitchenFree parkingAir conditioning
SUPERHOST
Private room in Pittsfield
Large guest suite w/private bath in the Berkshires
3 guests1 bedroom2 beds1 private bath
WifiKitchenFree parkingAir conditioning
Entire rental unit in Richmond
Lake level Apartment with view and direct access.
2 guests1 bedroom2 beds1 bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire rental unit in Pittsfield
Berkshires Charm, Downtown Convenience
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire cottage in Pittsfield
Berkshire Lakeview Tranquility
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
SUPERHOST
Private room in Pittsfield
Modern, Spacious Master Bedroom and Bathroom
2 guests1 bedroom2 beds1.5 baths
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire residential home in Pittsfield
Berkshire Lakefront House w/free kayaks/SUP/ Canoe
5 guests2 bedrooms3 beds1.5 baths
WifiKitchenFree parkingAir conditioning
SUPERHOST
Private room in Dalton
Dalton in the Beautiful Berkshires
3 guests1 bedroom2 beds1 private bath
WifiKitchenFree parkingAir conditioning
SUPERHOST
Entire rental unit in Pittsfield
Berkshire Luxury Apartment (Deal Sept 25-Oct 1)
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parkingAir conditioning
1–20 of 141 places to stay
Enter dates and number of guests to see the total price per night.