Skip to content
110 stays

Stays in Pittsfield

Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
Private room in Pittsfield
Queen Room w/Private Bath in Quiet Berkshires Home
2 guests1 bedroom1 bed1 private bath
WifiAir conditioningFree parking
Rating 4.99 out of 5;102 reviews
Price:$ 73 / night
SUPERHOST
Entire cottage in Pittsfield
The Oliver Wendell Holmes Guesthouse @ Holmesdale
4 guests1 bedroom3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.85 out of 5;20 reviews
Price:$ 398 / night
SUPERHOST
Entire apartment in Pittsfield
Charming Apartment inThe Heart of The Berkshires 2
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.88 out of 5;17 reviews
Price:$ 125 / night
Room in boutique hotel in Lee
Pilgrim Inn: Room 103, 2 Queen Beds
4 guests1 bedroom2 beds1 private bath
WifiAir conditioningFree parking
Rating 3.80 out of 5;10 reviews
Price:$ 61 / night
SUPERHOST
Entire house in Lenox
Artists' Family Home
6 guests3 bedrooms4 beds1.5 baths
WifiKitchenFree parking
Rating 4.92 out of 5;75 reviews
Price:$ 311 / night
SUPERHOST
Entire guesthouse in Lenox
The East Street Cabin
2 guestsStudio1 bed1 bath
KitchenFree parking
Rating 5.0 out of 5;14 reviews
Price:$ 175 / night
SUPERHOST
Entire condominium in Hancock
Furnished Condo at Jiminy Peak (For Sale)
6 guests2 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.93 out of 5;15 reviews
Price:$ 173 / night
Entire house in Pittsfield
Berkshires best
12 guests4 bedrooms5 beds2 baths
WifiKitchenFree parking
Price:$ 400 / night
SUPERHOST
Room in boutique hotel in Lenox
Terrace House King
2 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.80 out of 5;5 reviews
Price:$ 230 / night
Entire apartment in Hancock
Wyndham Bentley Brook, MA Christmas, Dec 25-30 Sky
8 guests2 bedrooms4 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$ 280 / night
SUPERHOST
Entire apartment in Pittsfield
Beautiful 1 Bedroom Nestled in the Berkshires
4 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$ 199 / night
Entire condominium in Williamstown
Vacation Village in the Berkshires Resort Suite A
4 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$ 121 / night
Entire condominium in Hancock
Cozy Condo @ Jiminy Peak
5 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.67 out of 5;33 reviews
Price:$ 145 / night
Private room in Canaan
Standard Queen/Full
4 guestsStudio1 bath
Air conditioningFree parking
Price:$ 99 / night
SUPERHOST
Entire house in Lenox
Lenox Farmhouse, short walk to town, private pool!
4 guests3 bedrooms4 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;13 reviews
Price:$ 444 / night
Private room in Stockbridge
Villa Favorita
2 guests1 bedroom1 bed1 private bath
WifiAir conditioningFree parking
Price:$ 100 / night
Entire condominium in Hancock
Jiminy Peak Country Inn 1 Bedroom Suite
4 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.50 out of 5;18 reviews
Price:$ 94 / night
SUPERHOST
Resort room in Hancock
WYNDHAM BENTLEY BROOK AT JIMINY PEAK SKI MOUNTAIN
8 guests2 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$ 350 / night
Entire house in Chatham
Clatter Hall
8 guests4 bedrooms5 beds3 baths
WifiAir conditioningKitchenFree parking
Price:$ 543 / night
SUPERHOST
Entire guest suite in East Nassau
Star Gazer Farm
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.95 out of 5;37 reviews
Price:$ 250 / night
1 20 of 110 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.