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300+ stays

Stays in Pittsfield

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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 guest suite in Lanesborough
Private Suite in the Beautiful Berkshires
6 guests3 bedrooms4 beds2 baths
WifiAir conditioningFree parking
Rating 4.96 out of 5;113 reviews
Price:$129 / night
SUPERHOST
Entire house in East Chatham
Windswept Acres In the Berkshires~Canaan, New York
4 guests3 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.88 out of 5;86 reviews
Price:$202 / night
SUPERHOST
Farm stay in New Lebanon
Shadowbrook Farm Stay
4 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.94 out of 5;49 reviews
Price:$307 / night
SUPERHOST
Entire guest suite in Richmond
CovidClean/Tanglewood/Private Ranch/Views/Pets/Ski
5 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.93 out of 5;55 reviews
Price:$185 / night
SUPERHOST
Entire apartment in New Lebanon
Sunny Duplex at the old boarding house
5 guests2 bedrooms4 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.94 out of 5;106 reviews
Price:$115 / night
SUPERHOST
Entire apartment in Pittsfield
Sharon's Place 4 ..... pets, and 420 friendly!!!!
2 guestsStudio1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.71 out of 5;70 reviews
Price:$45 / night
SUPERHOST
Private room in Pittsfield
Cozy and Quiet in the Berkshires
3 guests1 bedroom2 beds1 private bath
WifiAir conditioningFree parking
Rating 4.97 out of 5;94 reviews
Price:$132 / night
Entire cottage in New Lebanon
Carriage house suite in heart of the Berkshires
7 guests1 bedroom4 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.75 out of 5;40 reviews
Price:$98 / 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:$170 / night
Entire apartment in New Lebanon
Chalet-style loft on farm near Tanglewood
5 guests1 bedroom3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.72 out of 5;54 reviews
Price:$99 / night
SUPERHOST
Entire house in Lenox
Modern,Comfortable, Classic House-Downtown Lenox
10 guests4 bedrooms6 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;34 reviews
Price:$399 / night
SUPERHOST
Entire house in Austerlitz
Peaceful Country House in the Berkshires
6 guests4 bedrooms4 beds3 baths
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;47 reviews
Price:$232 / night
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
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 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
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
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 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
1 20 of 300+ places to stay
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