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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 4.80 out of 5;74 reviews
Price:$78 / night
Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.80 out of 5;214 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
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:$360 / 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 guest suite in Williamstown
Berkshire Guest Suite
2 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 4.96 out of 5;71 reviews
Price:$62 / 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
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;188 reviews
Price:$90 / night
Entire house in Pittsfield
Spacious and quiet central Berkshire home!
6 guests4 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$85 / 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 house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.97 out of 5;125 reviews
Price:$155 / night
SUPERHOST
Entire house in Pittsfield
Spacious Duplex in Heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;83 reviews
Price:$195 / night
SUPERHOST
Private room in Pittsfield
Equestrian retreat
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningFree parking
Rating 5.0 out of 5;21 reviews
Price:$95 / 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 Lee
Comfortable living in 1870's house!
2 guests1 bedroom1 bed1.5 shared baths
WifiAir conditioningFree parking
Rating 4.89 out of 5;266 reviews
Price:$43 / night
Entire house in Becket
A Magical Spot on Little Robin Lake
4 guests2 bedrooms2 beds2 baths
WifiKitchenFree parking
Rating 4.58 out of 5;97 reviews
Price:$155 / 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;186 reviews
Price:$49 / 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;76 reviews
Price:$70 / 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;77 reviews
Price:$364 / night
1 20 of 300+ places to stay
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