Pittsfield Vacation Rentals - HolidayHomes base64Hash Pittsfield Vacation Rentals - HolidayHomes

Pittsfield Vacation Rentals

Browse 197 available vacation homes and compared across 8 trusted partners

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Top-Rated Vacation rentals in Pittsfield

Book the highest-rated Pittsfield vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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House Pittsfield
Vacation home with terrace, garden & barbecue | Lake view
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House Pittsfield
Beautiful Waterfront home with deep water dock on Onota Lake
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House Pittsfield
Vacation home with yard, grill & patio | Mountain view
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House Pittsfield
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks
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House Pittsfield
Elegant Pittsfield Home Near Downtown & Skiing!
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House Pittsfield
Dancing Horse Lodge
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House Pittsfield
Renovated Pittsfield Colonial by Evergreen Home
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House Pittsfield
Country Living just minutes from Everything!
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House Pittsfield
House with barbecue, patio & yard | Perfect for remote work
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House Pittsfield
House with view in the berkshires
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Cabin Pittsfield
Child-friendly cottage with patio, barbeque & yard | Nature view | Suitable for remote work
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House Pittsfield
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
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House Pittsfield
Spacious Historic Home in the Berkshires!
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House Pittsfield
House | Suitable for remote work
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Top 15 most Recommended Vacation Rentals in Pittsfield

Discover your ideal Pittsfield vacation rental with real-time comparisons of 197 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Pittsfield
House ∙ 9 guests ∙ 5 bedrooms

307 m² House

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield accommodates 9 guests and features a family-friendly kitchen for enjoyable gatherings.
from $277
per night
(24)
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Lodge Pittsfield
Lodge ∙ 4 guests ∙ 1 bedroom

79 m² Lodge

Pittsfield, Berkshire County, Massachusetts, United States
This cozy lodge in Pittsfield accommodates 4 guests and features a hot tub for relaxation after a day of adventure.
from $218
per night
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House Pittsfield
House ∙ 6 guests ∙ 3 bedrooms

163 m² House

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield accommodates 6 guests and features a family-friendly kitchen for a comfortable stay.
from $157
per night
(21)
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Apartment Pittsfield
8 guests ∙ 3 bedrooms

Apartment

Pittsfield, Berkshire County, Massachusetts, United States
Spacious apartment rental in Pittsfield for 8 guests featuring a beautiful balcony with mountain views.
from $386
per night
(21)
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House Pittsfield
6 guests ∙ 3 bedrooms

House

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield accommodates 6 guests and features a cozy fireplace for added comfort.
from $242
per night
(10)
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Condo Pittsfield
8 guests ∙ 4 bedrooms

Condo

Pittsfield, Berkshire County, Massachusetts, United States
This spacious condo in Pittsfield accommodates 8 guests and features a cozy fireplace for a comfortable stay.
from $662
per night
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House Pittsfield
14 guests ∙ 6 bedrooms

House

Pittsfield, Berkshire County, Massachusetts, United States
This spacious house rental in Pittsfield accommodates 14 guests and features a cozy fireplace for warmth and comfort.
from $755
per night
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Apartment Pittsfield
2 guests ∙ 1 bedroom

Apartment

Pittsfield, Berkshire County, Massachusetts, United States
This apartment rental in Pittsfield accommodates 2 and includes convenient parking for residents.
from $134
per night
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Accommodation Pittsfield
3 guests ∙ 1 bedroom

Accommodation

Pittsfield, Berkshire County, Massachusetts, United States
This cozy accommodation in Pittsfield accommodates 3 guests and offers convenient parking for your stay.
from $112
per night
(272)
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