Vacation Rentals By Owner In Stockbridge, MA

Villa

Historic Stockbridge Villa on 25 acres

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(61)

$999.34

InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(14)

$298.81

Cabin

Cozy Cabin on Lake Mahkeenac

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(7)

Select Dates for Price

Cottage

Beachwood Cottage

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$392.39

Brand New Barn House w/ EV charger

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(99)

$670.2

Modern Cottage in the heart of the Berkshires with new exterior flex space!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(73)

$413.29

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$442.33

Cabin

Lakeshore cabin with beach and dock

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(40)

$855.62

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(10)

$612.4

Waterfront log cabin down a private dirt road next to Tanglewood

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$172.72

Apartment

2 Mi to Norman Rockwell Museum: Stockbridge Apt!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$496.88

Refined Berkshires Haven. Between Stockbridge & Lenox. Nature, Arts & Wellness

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$404.73

Apartment

Clean & Modern space with a mix of original warmth and charming renovation.

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$535.2

Charming cottage in Norman Rockwell's Stockbridge with two decks!

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$795.6

Elegant & private light-filled privacy

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$754.43

Chic Homestead Experience, Pick-and-Eat Gardens!

Stockbridge, Massachusetts, United States

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Bath

Sleeps

Exceptional(20)

$415.15

Stockbridge Home: Walk to Town Beach!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$749.96

Apartment

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(21)

$548.14

Classic Stockbridge Cottage

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$912.59

View 38 Private vacation home

Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities

Stockbridge, Massachusetts, United States

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Rent a place that suits your needs

Private vacation home

Most popular vacation rentals in Stockbridge

$408.45

A Charming Mid 1800's Stockbridge Farmhouse.

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$459.60

Hearth House | Prime Location!

Stockbridge, Massachusetts, United States

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Bath

Sleeps

$448.03

Two Blocks from the Red Lion Inn & next to Berkshire Theater

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$442.33

Cabin

Lakeshore cabin with beach and dock

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$415.15

Stockbridge Home: Walk to Town Beach!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$413.29

Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$410.31

Tranquil 3 BR Stockbridge House w/ Private Deck!

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$402.45

Stockbridge Landings | 3 Mins To Tanglewood

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$344.63

Stockbridge pied-à-terre

Stockbridge, Massachusetts, United States

Bed

Bath

Sleeps

$392.39