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300+ stays

Stays in Pittsfield

SUPERHOST
Entire cottage in Becket
BERKSHIRE COTTAGE BY CRYSTAL CLEAR LAKE
4 guests2 bedrooms2 beds1 bath
KitchenAir conditioningSelf check-inFree parking
Rating 4.95 out of 5;62 reviews
Price:$172 / night
SUPERHOST
Entire cottage in Hinsdale
Cozy cottage in the Berkshires
4 guests2 bedrooms3 beds1 bath
KitchenWifiFree parkingIndoor fireplace
Rating 4.97 out of 5;38 reviews
Price:$145 / night
Entire house in Lenox
Mid-Century Modern Chic in Lenox
4 guests2 bedrooms2 beds2 baths
KitchenAir conditioningWifiSelf check-in
Rating 4.51 out of 5;70 reviews
Price:$149 / night
SUPERHOST
Entire apartment in Pittsfield
Marie's Place
4 guests2 bedrooms2 beds1 bath
KitchenWifiSelf check-inFree parking
Rating 4.89 out of 5;116 reviews
Price:$95 / night
Entire cottage in Lanesborough
Berkshires Waterfront Lakehouse
6 guests3 bedrooms4 beds1.5 baths
KitchenAir conditioningWifiSelf check-in
Rating 4.86 out of 5;98 reviews
Price:$225 / night
Entire cabin in Pittsfield
Summer Cottage in the Berkshires
3 guests2 bedrooms2 beds1 bath
KitchenAir conditioningWifiFree parking
Rating 4.90 out of 5;75 reviews
Price:$140 / night
SUPERHOST
Private room in Pittsfield
Berkshires “Cottage” Edmister House The Arden Room
2 guests1 bedroom1 bed1 private bath
KitchenAir conditioningBreakfastWifi
Rating 4.95 out of 5;148 reviews
Price:$125 / night
SUPERHOST
Entire cottage in West Stockbridge
Cozy Stockbridge Cottage
5 guests2 bedrooms3 beds1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.81 out of 5;114 reviews
Price:$98 / night
SUPERHOST
Entire apartment in Pittsfield
Heart Of The Berkshires
5 guests3 bedrooms3 beds1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.96 out of 5;93 reviews
Price:$135 / night
SUPERHOST
Entire house in Pittsfield
Charming Berkshire Getaway with Scenic Lake Views
4 guests2 bedrooms2 beds1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.75 out of 5;4 reviews
Price:$225 / night
SUPERHOST
Entire cottage in Williamstown
Cute Cozy Comfy Cottage in the Berkshires
4 guests1 bedroom1 bed1 bath
KitchenWifiFree parkingIndoor fireplace
Rating 4.88 out of 5;48 reviews
Price:$132 / night
Entire cottage in Great Barrington
Artist Cottage at the Foot of Monument Mountain
2 guests1 bedroom1 bed2 baths
KitchenAir conditioningWifiSelf check-in
Rating 4.94 out of 5;53 reviews
Price:$193 / night
SUPERHOST
Entire house in Washington
Craftsman home in the Berkshires
5 guests2 bedrooms3 beds2 baths
KitchenWifiSelf check-inFree parking
Rating 4.93 out of 5;59 reviews
Price:$200 / night
SUPERHOST
Entire house in Lee
Cozy Berkshires Cottage
4 guests1 bedroom1 bed1 bath
KitchenAir conditioningBreakfastWifi
Rating 4.87 out of 5;115 reviews
Price:$122 / night
Private room in Lenox
One private single room in Lenox
2 guests1 bedroom1 bed1.5 shared baths
KitchenBreakfastWifiFree parking
Rating 4.98 out of 5;51 reviews
Price:$50 / night
SUPERHOST
Entire apartment in Pittsfield
Charming Apartment inThe Heart of The Berkshires 2
2 guests1 bedroom1 bed1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.81 out of 5;26 reviews
Price:$125 / night
SUPERHOST
Entire cabin in Savoy
The Camp - 20 Minutes to Berkshire East!
4 guests1 bedroom1 bed1 bath
KitchenWifiFree parkingWasher
Rating 4.97 out of 5;33 reviews
Price:$99 / night
SUPERHOST
Entire cottage in Pittsfield
The Oliver Wendell Holmes Guesthouse @ Holmesdale
4 guests1 bedroom3 beds1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.86 out of 5;29 reviews
Price:$425 / night
Entire apartment in Otis
Rustic Berkshire Getaway
4 guests2 bedrooms2 beds2 baths
KitchenAir conditioningWifiSelf check-in
Rating 4.93 out of 5;15 reviews
Price:$139 / night
SUPERHOST
Entire cottage in New Lebanon
The Writer's Cottage
3 guests1 bedroom2 beds1 bath
KitchenAir conditioningWifiSelf check-in
Rating 4.95 out of 5;112 reviews
Price:$108 / night
21 40 of 300+ places to stay
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