Home Vacation Rentals By Owner In Pittsfield, MA

Showing 20 Of 51 Vacation Rentals
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$423.44

/ Nightly
Private Vacation Home

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Richmond, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$185.75

/ Nightly
Apartment

Cozy Renovated with 1 parking space

Pittsfield, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(49)

$667.09

/ Nightly
Private Vacation Home

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

Pittsfield, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 14

Sleeps
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Exceptional(116)

$392.36

/ Nightly
Private Vacation Home

Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 7

Sleeps
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Exceptional(1)

$126.59

/ Nightly
Apartment

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Pittsfield, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$178.72

/ Nightly
Apartment

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Pittsfield, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps
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Exceptional(2)

$382.41

/ Nightly
Private Vacation Home

Cozy Pittsfield Gem w/ Deck, Gazebo & Fireplace!

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 10

Sleeps
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Exceptional(31)

$197.26

/ Nightly
Condo

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Hancock, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(23)

$292.53

/ Nightly
Apartment

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$477.52

/ Nightly
Private Vacation Home

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(10)

$492.71

/ Nightly
Private Vacation Home

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(1)

$241.34

/ Nightly
Country House

Charming & Bright Berkshires Field House

Pittsfield, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$1052.04

/ Nightly
Private Vacation Home

Grand Berkshire Manor By Evergreen Home

Pittsfield, Massachusetts, United States

Bed 5

Bed

Bath 4

Bath

Sleep 10

Sleeps
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Exceptional(95)

$400.82

/ Nightly
Private Vacation Home

Featured in a Home & Garden TV Special 30 South Mountain Road

Pittsfield, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(16)

$773.8

/ Nightly
Private Vacation Home

Hidden Oasis in the Mountains by Evergreen Home

Pittsfield, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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$334.36

/ Nightly
Private Vacation Home

Lake View Cozy Cottage

Pittsfield, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps
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$748.73

/ Nightly
Condo

Perfect for Winter Skiing!!

Pittsfield, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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$312.39

/ Nightly
Private Vacation Home

Fall Fun in the Berkshires: Yard, Patio, Playset

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(50)

$318.9

/ Nightly
Private Vacation Home

Dancing Horse Lodge

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(2)

$877.97

/ Nightly
Private Vacation Home

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

Pittsfield, Massachusetts, United States

Bed 5

Bed

Bath 3

Bath

Sleep 10

Sleeps
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Private vacation home

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View 37 Private vacation home

Home Most popular vacation rentals in Pittsfield

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Exceptional(2)

$404.36

/ Nightly
Cabin

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

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(2)

$643.94

/ Nightly
Private vacation home

Modern 4 bedroom lakefront house in The Berkshires.

Pittsfield, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(2)

$611.52

/ Nightly
Private vacation home

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield, Massachusetts, United States

Bed 4

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(2)

$580.31

/ Nightly
Private vacation home

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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Exceptional(2)

$560.74

/ Nightly
Private vacation home

Country Living just minutes from Everything!

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 8

Sleeps
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Exceptional(2)

$493.71

/ Nightly
Apartment

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

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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Exceptional(2)

$477.52

/ Nightly
Private vacation home

Solomon Ely Homestead - Charming Pittsfield Stay

Pittsfield, Massachusetts, United States

Bed 4

Bed

Bath 1

Bath

Sleep 7

Sleeps
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Exceptional(2)

$292.53

/ Nightly
Apartment

Private apartment in beautiful country barn

Richmond, Massachusetts, United States

Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps
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Exceptional(2)

$280.18

/ Nightly
Private vacation home

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

Pittsfield, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 5

Sleeps
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Exceptional(2)

$286.45

/ Nightly
Private vacation home

Dharma Grove - Bask in the Light

Pittsfield, Massachusetts, United States

Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps

Most Popular Cities in Massachusetts