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300+ stays

Stays in Pittsfield

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SUPERHOST
Entire apartment in Pittsfield
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.79 out of 5;82 reviews
Price:$43 / night
SUPERHOST
Entire apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.79 out of 5;75 reviews
Price:$73 / night
Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;216 reviews
Price:$97 / night
SUPERHOST
Entire cottage in Lanesborough
The Sail Loft
4 guests1 bedroom2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.91 out of 5;22 reviews
Price:$84 / night
Entire apartment in Pittsfield
One Bedroom in Downtown
2 guests1 bedroom0 beds1 bath
WifiKitchenFree parking
Rating 4.80 out of 5;5 reviews
Price:$85 / night
Entire cottage in Hinsdale
Lakeside 3 bd Berkshires Getaway Relax with Us
8 guests3 bedrooms3 beds1 bath
WifiKitchenFree parking
Rating 4.57 out of 5;25 reviews
Price:$125 / night
SUPERHOST
Entire apartment in Pittsfield
Marie's Place
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.89 out of 5;107 reviews
Price:$100 / night
SUPERHOST
Entire cottage in Pittsfield
The Oliver Wendell Holmes Guesthouse @ Holmesdale
4 guests1 bedroom3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;21 reviews
Price:$388 / night
SUPERHOST
Entire bungalow in Pittsfield
The Lakehouse
6 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;43 reviews
Price:$125 / night
SUPERHOST
Private room in Pittsfield
Large guest suite w/private bath in the Berkshires
3 guests1 bedroom2 beds1 private bath
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;190 reviews
Price:$90 / night
Entire apartment in Albany Area
Cozy Suite with huge bar and stone fireplace!
4 guestsStudio1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.61 out of 5;187 reviews
Price:$50 / night
SUPERHOST
Entire cottage in Becket
BERKSHIRE COTTAGE BY CRYSTAL CLEAR LAKE
4 guests2 bedrooms2 beds1 bath
Air conditioningKitchenFree parking
Rating 4.94 out of 5;54 reviews
Price:$172 / night
SUPERHOST
Entire house in Pittsfield
Beautiful House By The Lake W/Jetted Hot Tub
16+ guests8 bedrooms14 beds3 baths
WifiKitchenFree parking
Rating 4.78 out of 5;78 reviews
Price:$364 / night
Entire house in Pittsfield
Beautiful 4 Bedroom HOME Berkshire getaway
7 guests4 bedrooms4 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.89 out of 5;9 reviews
Price:$193 / night
SUPERHOST
Private room in Pittsfield
Equestrian retreat
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;23 reviews
Price:$96 / night
SUPERHOST
Entire apartment in Pittsfield
Heart Of The Berkshires
5 guests3 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.95 out of 5;83 reviews
Price:$135 / night
SUPERHOST
Entire house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.97 out of 5;126 reviews
Price:$155 / night
Entire cabin in Pittsfield
Summer Cottage in the Berkshires
3 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.90 out of 5;73 reviews
Price:$140 / night
Entire cottage in Lanesborough
Berkshires Waterfront Lakehouse
6 guests3 bedrooms4 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;93 reviews
Price:$250 / night
Entire cabin in Lanesborough
Luxury cabins
4 guestsStudio3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.75 out of 5;4 reviews
Price:$139 / night
1 20 of 300+ places to stay
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