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300+ stays

Stays in Pittsfield

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SUPERHOST
Entire apartment in North Adams
Guest Apt. Near MCLA & MASS MoCA
2 guests1 bedroom0 beds1 bath
WifiKitchenFree parking
Rating 4.94 out of 5;514 reviews
Price:$99 / 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
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 cottage in Becket
Berkshires Modern Comfy Private Retreat! Hot tub!
6 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.72 out of 5;190 reviews
Price:$175 / 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
Marie's Place
4 guests2 bedrooms2 beds1 bath
WifiKitchenFree parking
Rating 4.89 out of 5;107 reviews
Price:$100 / 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
Entire cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
4 guests1 bedroom1 bed1 bath
WifiKitchenFree parking
Rating 4.86 out of 5;43 reviews
Price:$132 / night
SUPERHOST
Entire guest suite in Richmond
CovidClean/Tanglewood/Private Ranch/Views/Pets/Ski
5 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.92 out of 5;53 reviews
Price:$183 / 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:$174 / 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:$98 / 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 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;214 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:$76 / 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 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 cottage in Becket
BERKSHIRE COTTAGE BY CRYSTAL CLEAR LAKE
4 guests2 bedrooms2 beds1 bath
Air conditioningKitchenFree parking
Rating 4.96 out of 5;53 reviews
Price:$169 / 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:$379 / night
1 20 of 300+ places to stay
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