Vacation Home Rentals By Owner In Pittsfield, MA

Showing 20 Of 37 Vacation Rentals

Exceptional(19)

$797.54

/ Nightly

Private Vacation Home

Ray of Sunshine Berkshire Home on Pontoosuc Lake

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(11)

$580.31

/ Nightly

Private Vacation Home

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(19)

$605.9

/ Nightly

Private Vacation Home

Elegant Pittsfield Home Near Downtown & Skiing!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(8)

$611.52

/ Nightly

Private Vacation Home

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(101)

$643.94

/ Nightly

Private Vacation Home

Modern 4 bedroom lakefront house in The Berkshires.

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(49)

$667.09

/ Nightly

Private Vacation Home

Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(35)

$695.21

/ Nightly

Private Vacation Home

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$702.62

/ Nightly

Private Vacation Home

Modern, Renovated Lakefront Escape

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$725.31

/ Nightly

Private Vacation Home

Cape Home In the Beautiful Berkshires - Near Lenox & Bousquet

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(16)

$773.8

/ Nightly

Private Vacation Home

Hidden Oasis in the Mountains by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(30)

$560.74

/ Nightly

Private Vacation Home

Country Living just minutes from Everything!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(3)

$810.39

/ Nightly

Private Vacation Home

Large open floor plan. Private yet close to everything. Lovely meadow views

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(66)

$861.21

/ Nightly

Private Vacation Home

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(89)

$872

/ Nightly

Private Vacation Home

Tranquil Lake House Getaway on Onota Lake

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(37)

$875.17

/ Nightly

Private Vacation Home

Lakeside Home With Pool-Completely Renovated

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$877.97

/ Nightly

Private Vacation Home

Spacious 5BR Farmhouse • Sleeps 10 • Perfect for Families • Near Two Lakes

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$1052.04

/ Nightly

Private Vacation Home

Grand Berkshire Manor By Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(116)

$1332.58

/ Nightly

Private Vacation Home

Berkshire Lake Beauty-Modern Amenities On The Lake

Pittsfield, Massachusetts, United States

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Bath

Sleeps

Exceptional(9)

$1601.22

/ Nightly

Private Vacation Home

Spacious Luxury Berkshire's Estate on 21 acres

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$382.41

/ Nightly

Private Vacation Home

Cozy Pittsfield Gem w/ Deck, Gazebo & Fireplace!

Pittsfield, Massachusetts, United States

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Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 37 Private vacation home

Most popular vacation rentals in Pittsfield

Exceptional(2)

$404.36

/ Nightly

Cabin

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$643.94

/ Nightly

Private vacation home

Modern 4 bedroom lakefront house in The Berkshires.

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$611.52

/ Nightly

Private vacation home

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$580.31

/ Nightly

Private vacation home

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$560.74

/ Nightly

Private vacation home

Country Living just minutes from Everything!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$493.71

/ Nightly

Apartment

Cozy Duplex in Pittsfield: 1 Mile to Onota Lake – Near Bousquet & Jiminy Peak

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$477.52

/ Nightly

Private vacation home

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$292.53

/ Nightly

Apartment

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$280.18

/ Nightly

Private vacation home

Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(2)

$286.45

/ Nightly

Private vacation home

Dharma Grove - Bask in the Light

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Pittsfield, MA

$797.54

$580.31

$605.9

$611.52

$643.94

$667.09

$695.21

$702.62

$725.31

$773.8

$560.74

$810.39

$861.21

$872

$875.17

$877.97

$1052.04

$1332.58

$1601.22

$382.41

Rent a place that suits your needs

Most popular vacation rentals in Pittsfield

$404.36

$643.94

$611.52

$580.31

$560.74

$493.71

$477.52

$292.53

$280.18

$286.45

Most Popular Cities in Massachusetts