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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
WifiKitchenAir conditioningFree parking
Rating 4.80 out of 5;213 reviews
Price:$80 / night
SUPERHOST
Entire apartment in Pittsfield
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.79 out of 5;77 reviews
Price:$43 / night
SUPERHOST
Entire apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.80 out of 5;71 reviews
Price:$75 / night
SUPERHOST
Entire cottage in Lanesborough
The Sail Loft
4 guests1 bedroom2 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.89 out of 5;19 reviews
Price:$85 / night
SUPERHOST
Entire house in Pittsfield
Spacious Duplex in Heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.99 out of 5;76 reviews
Price:$190 / night
SUPERHOST
Private room in Pittsfield
Private Room and Bathroom - Clean and Spacious
2 guests1 bedroom1 bed1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.93 out of 5;28 reviews
Price:$48 / night
SUPERHOST
Entire apartment in Pittsfield
Downtown Apartment B
4 guests2 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.90 out of 5;41 reviews
Price:$89 / night
Entire cabin in Pittsfield
Summer Cottage in the Berkshires
3 guests2 bedrooms2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.91 out of 5;69 reviews
Price:$140 / night
SUPERHOST
Entire apartment in Pittsfield
Simply off North
2 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 5.0 out of 5;19 reviews
Price:$60 / 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:$90 / night
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;98 reviews
Price:$65 / night
SUPERHOST
Private room in Pittsfield
Large guest suite w/private bath in the Berkshires
3 guests1 bedroom2 beds1 private bath
WifiKitchenAir conditioningFree parking
Rating 4.98 out of 5;180 reviews
Price:$90 / night
SUPERHOST
Entire apartment in Pittsfield
Central Berkshires - comfy beds and fast internet!
6 guests3 bedrooms3 beds1.5 baths
WifiKitchenFree parking
Rating 4.85 out of 5;28 reviews
Price:$62 / night
SUPERHOST
Entire bungalow in Pittsfield
The Lakehouse
6 guests2 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.86 out of 5;43 reviews
Price:$125 / night
Entire cottage in Pittsfield
DESIGNERS COTTAGE CK SEPT OCT "SPECIALS"
4 guests1 bedroom2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.81 out of 5;39 reviews
Price:$185 / night
SUPERHOST
Entire cottage in Pittsfield
The Oliver Wendell Holmes Guesthouse @ Holmesdale
4 guests1 bedroom3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.82 out of 5;17 reviews
Price:$389 / night
SUPERHOST
Entire chalet in Lee
Waterfront lakehouse in Berkshires
7 guests3 bedrooms3 beds1.5 baths
WifiKitchenFree parking
Rating 4.85 out of 5;40 reviews
Price:$200 / night
Entire apartment in Albany Area
Cozy Suite with huge bar and stone fireplace!
4 guestsStudio1 bed1 bath
WifiKitchenAir conditioningFree parking
Rating 4.61 out of 5;181 reviews
Price:$45 / night
SUPERHOST
Private room in Dalton
Spacious bedroom with private bath in Dalton, MA
3 guests1 bedroom2 beds1 private bath
WifiAir conditioningFree parking
Rating 4.97 out of 5;75 reviews
Price:$70 / night
SUPERHOST
Entire house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.98 out of 5;123 reviews
Price:$135 / night
1 20 of 300+ places to stay
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