Vacation Rentals By Owner In Pittsfield, MA

Showing 40 Of 51 Vacation Rentals

Exceptional(35)

$695.21

/ Nightly

Private Vacation Home

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$125.11

/ Nightly

Apartment

family friendly retreat condo

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(14)

$227.87

/ Nightly

Cottage

Charming Lakeview Cottage in Heart of the Berkshires

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(12)

$399.59

/ Nightly

Private Vacation Home

house with view in the berkshires

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$288.55

/ Nightly

Cottage

Pine & Paddle | Pond Access • Kayaks

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$286.45

/ Nightly

Private Vacation Home

Dharma Grove - Bask in the Light

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(147)

$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(19)

$605.9

/ Nightly

Private Vacation Home

Elegant Pittsfield Home Near Downtown & Skiing!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$280.18

/ Nightly

Private Vacation Home

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

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(9)

$1601.22

/ Nightly

Private Vacation Home

Spacious Luxury Berkshire's Estate on 21 acres

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(11)

$250.67

/ Nightly

Private Vacation Home

Idyllic Berkshires Farmhouse

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

$299.86

/ Nightly

Private Vacation Home

The Reel Retreat | Theatre & Firepit • Game Room

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$268.08

/ Nightly

Private Vacation Home

Cozy cottage in the Berkshires

PITTSFIELD, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(19)

$797.54

/ Nightly

Private Vacation Home

Ray of Sunshine Berkshire Home on Pontoosuc Lake

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

$369.16

/ Nightly

Condo

Berkshire Mountainside Condo

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 37 Private vacation home

Most popular vacation rentals in Pittsfield

$404.36

/ Nightly

Cabin

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

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$643.94

/ Nightly

Private vacation home

Modern 4 bedroom lakefront house in The Berkshires.

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$611.52

/ Nightly

Private vacation home

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$580.31

/ Nightly

Private vacation home

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$560.74

/ Nightly

Private vacation home

Country Living just minutes from Everything!

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$493.71

/ Nightly

Apartment

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

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$477.52

/ Nightly

Private vacation home

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$292.53

/ Nightly

Apartment

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed

Bath

Sleeps

$280.18

/ Nightly

Private vacation home

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

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

$286.45

/ Nightly

Private vacation home

Dharma Grove - Bask in the Light

Pittsfield, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Pittsfield, MA

$695.21

$125.11

$227.87

$875.17

$399.59

$288.55

$286.45

$404.36

$605.9

$280.18

$560.74

$810.39

$1601.22

$580.31

$250.67

$299.86

$268.08

$797.54

$702.62

$369.16

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