Skip to content
22 stays

Stays in Pittsfield

Review COVID-19 travel restrictions before you book.
Learn more
SUPERHOST
Entire condominium in Hancock
Furnished Condo at Jiminy Peak (For Sale $288,000)
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.95 out of 5;21 reviews
Price:$171 / night
Entire condominium in Hancock
Jiminy Peak Country Inn 1 Bedroom Suite
4 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.55 out of 5;22 reviews
Price:$92 / night
Entire condominium in Hancock
Cozy Condo @ Jiminy Peak
5 guests2 bedrooms2 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.67 out of 5;33 reviews
Price:$145 / night
Entire condominium in Williamstown
Jiminy Peak Condo on the mountainside
6 guests2 bedrooms5 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;5 reviews
Price:$200 / night
Entire condominium in Hancock
Berkshires Jiminy Peak Mountainside Condo
6 guests2 bedrooms4 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;12 reviews
Price:$249 / night
Entire condominium in Williamstown
Vacation Village in the Berkshires Resort Suite A
4 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioningFree parking
Price:$121 / night
Entire condominium in Lee
Berkshires Resort, Lee, MA—Prime Tanglewood Weeks
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Price:$215 / night
Entire condominium in Lee
Fox Hollow Lakeside Condo, Minutes to Tanglewood
12 guests5 bedrooms8 beds3 baths
WifiKitchenAir conditioningFree parking
Price:$219 / night
SUPERHOST
Entire condominium in Lenox
Heart of Lenox!! - Renovated downtown apartment
4 guests2 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.83 out of 5;49 reviews
Price:$291 / night
Entire condominium in Lee
A home in heaven
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.73 out of 5;11 reviews
Price:$235 / night
SUPERHOST
Entire condominium in Lee
Oak N' Spruce Resort, near Tanglewood
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.82 out of 5;11 reviews
Price:$183 / night
Private room in Pittsfield
Downtown Beauty
2 guests1 bedroom1 bed1 shared bath
WifiKitchenAir conditioning
Rating 4.96 out of 5;25 reviews
Price:$109 / night
SUPERHOST
Entire condominium in Lee
Oak'n Spruce Resort in Berkshires, MA
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.92 out of 5;13 reviews
Price:$183 / night
Entire condominium in West Stockbridge
Cozy&Modern Near Tanglewood Kripalu
6 guests2 bedrooms2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.53 out of 5;37 reviews
Price:$239 / night
Entire condominium in Lee
15 mins from Tanglewood
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Price:$200 / night
SUPERHOST
Entire condominium in Lee
Berkshires Resort Presidential, Tanglewood, etc
6 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.75 out of 5;5 reviews
Price:$306 / night
Entire condominium in Hancock
Jiminy Peak Ski Thanksgiving Vacation
8 guests2 bedrooms3 beds2 baths
WifiKitchenAir conditioningFree parking
Price:$179 / night
Entire condominium in Lee
Holiday Inn Club/ Oak and Spruce, Berkshires
4 guests2 bedrooms2 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;4 reviews
Price:$215 / night
Entire condominium in Hancock
Vacation Village in the Berkshires
4 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioningFree parking
Price:$149 / night
Entire condominium in Lee
Fabulous Lakeside Condo Near Tanglewood
12 guests4 bedrooms10 beds4 baths
WifiKitchenAir conditioningFree parking
Price:$400 / night
1 20 of 22 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.