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300+ stays

Stays in Pittsfield

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Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;219 reviews
Price:$97 / 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:$142 / 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
SUPERHOST
Entire apartment in Pittsfield
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.78 out of 5;83 reviews
Price:$62 / 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;76 reviews
Price:$75 / 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
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:$174 / 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;188 reviews
Price:$50 / night
SUPERHOST
Private room in Pittsfield
Equestrian retreat
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;24 reviews
Price:$98 / 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;22 reviews
Price:$408 / night
SUPERHOST
Entire guest suite in Williamstown
Berkshire Guest Suite
2 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;73 reviews
Price:$66 / night
SUPERHOST
Entire cottage in Lanesborough
The Sail Loft
4 guests1 bedroom2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.88 out of 5;24 reviews
Price:$89 / night
SUPERHOST
Entire apartment in Pittsfield
Simply off North
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 5.0 out of 5;20 reviews
Price:$60 / night
Entire apartment in New Lebanon
Creamery loft near Hancock Shaker Village
6 guests2 bedrooms4 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.68 out of 5;34 reviews
Price:$98 / 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:$99 / night
SUPERHOST
Entire house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.97 out of 5;127 reviews
Price:$155 / night
Entire apartment in Pittsfield
Beautiful Berkshire County Apartment
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 4.71 out of 5;7 reviews
Price:$85 / night
SUPERHOST
Entire cottage in Hinsdale
Cozy cottage in the Berkshires
4 guests2 bedrooms3 beds1 bath
WifiKitchenFree parking
Rating 4.97 out of 5;36 reviews
Price:$145 / night
Entire house in Lenox
Mid-Century Modern Chic in Lenox
4 guests2 bedrooms2 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.50 out of 5;64 reviews
Price:$200 / night
Entire cabin in Stockbridge
Charming Stockbridge Cabin
8 guests4 bedrooms6 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;4 reviews
Price:$212 / night
1 20 of 300+ places to stay
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