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300+ stays

Stays in Pittsfield

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Entire cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
8 guests3 bedrooms4 beds2 baths
WifiKitchenHeating
Price:$225 / night
Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiKitchenHeating
Price:$120 / night
Entire house in Pittsfield
Berkshire Lakehouse - 3 bedrooms - sleeps 5
5 guests3 bedrooms3 beds1 bath
WifiKitchenHeating
Price:$175 / night
Entire cottage in Lanesborough
Berkshires Waterfront Lakehouse
6 guests3 bedrooms4 beds1.5 baths
WifiKitchenHeating
Price:$225 / night
SUPERHOST
Entire apartment in Pittsfield
Berkshires Charm, Downtown Convenience
4 guests2 bedrooms2 beds1 bath
WifiKitchenHeating
Price:$100 / night
SUPERHOST
Entire house in Chester
Riverfront Getaway
4 guests2 bedrooms2 beds1 bath
WifiKitchenIndoor fireplaceHeating
Price:$135 / night
Entire cottage in Great Barrington
Artist Cottage at the Foot of Monument Mountain
2 guests1 bedroom1 bed2 baths
WifiKitchenIndoor fireplaceHeating
Price:$203 / night
Entire house in Lenox
Mid-Century Modern Chic in Lenox
4 guests2 bedrooms2 beds2 baths
WifiKitchenIndoor fireplaceHeating
Price:$175 / night
Entire house in Dalton
The Yellow House
3 guests1 bedroom2 beds1 bath
WifiKitchenHeating
Price:$62 / night
Entire cottage in Pittsfield
Cottage Getaway - access all the Berkshires offer!
4 guests1 bedroom1 bed1 bath
WifiKitchenHeating
Price:$150 / night
Entire apartment in Pittsfield
Beautiful Berkshire County Apartment
2 guests1 bedroom1 bed1 bath
WifiKitchenHeating
Price:$85 / night
Entire house in Pittsfield
Dancing Horse Lodge
6 guests3 bedrooms3 beds1 bath
WifiKitchenIndoor fireplaceHeating
Price:$142 / night
Entire house in Pittsfield
Historic Townhouse in the heart of The Berkshires!
6 guests3 bedrooms3 beds2.5 baths
WifiKitchenHeating
Price:$158 / night
SUPERHOST
Entire guest suite in Williamstown
Berkshire Guest Suite
2 guests1 bedroom1 bed1 bath
WifiHeating
Price:$65 / night
SUPERHOST
Entire apartment in Otis
Rustic Berkshire Getaway
4 guests2 bedrooms2 beds2 baths
WifiKitchenHeating
Price:$117 / night
SUPERHOST
Entire apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiKitchenHeating
Price:$75 / night
SUPERHOST
Entire guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
4 guests1 bedroom3 beds1 bath
WifiKitchenHeating
Price:$145 / night
SUPERHOST
Entire apartment in Pittsfield
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bath
WifiKitchenHeating
Price:$45 / night
SUPERHOST
Entire cottage in Hinsdale
Lakeside 3 bd Berkshires Getaway Relax with Us
8 guests3 bedrooms3 beds1 bath
WifiKitchenHeating
Price:$160 / night
Room in boutique hotel in Lenox
Terrace House King
2 guests1 bedroom1 bed1 bath
WifiHeating
Price:$118 / night
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1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.