Stockbridge, Massachusetts

Vacation Rentals in Stockbridge, Massachusetts

Discover 24 vacation rental properties in Stockbridge. From 1 to 6 bedrooms. Average $394/night. 100% have pools.

24 verified listings Book securely on VRBO Prices updated March 2026

24 properties available

Stockbridge Home, Come Experience The Berkshires!

Stockbridge Home, Come Experience The Berkshires!

3 beds 2 baths
PoolA/CWiFiBalcony
$310/night
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New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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Artist's Camp on Lake Mahkeenac

Artist's Camp on Lake Mahkeenac

2 beds
PoolA/CWiFiBalcony
$230/night
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Stockbridge Village Cottage With Mountain View’s and walk to town

Stockbridge Village Cottage With Mountain View’s and walk to town

3 beds 2 baths
PoolA/CWiFiBalcony
$331/night
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Tranquil 3 BR Stockbridge House w/ Private Deck!

Tranquil 3 BR Stockbridge House w/ Private Deck!

3 beds 1 bath
PoolA/CWiFiBalcony
$370/night
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Stockbridge Home: Walk to Town Beach!

Stockbridge Home: Walk to Town Beach!

3 beds 1 bath
PoolA/CWiFiBalcony
$239/night
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Lakeshore cabin with private beach and dock

Lakeshore cabin with private beach and dock

3 beds 2 baths
PoolA/CWiFiBalcony
$414/night
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Stockbridge Vacation by Norman Rockwell

Stockbridge Vacation by Norman Rockwell

2 beds 2 baths
PoolA/CWiFiBalcony
$253/night
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Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!

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

4 beds 2 baths
PoolA/CWiFiBalcony
$234/night
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Charming cottage in the heart of the Berkshires!

Charming cottage in the heart of the Berkshires!

1 bed 1 bath
PoolA/CWiFiBalcony
$240/night
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Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!

Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!

2 beds
PoolA/CWiFiBalcony
$199/night
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Cozy Cabin on Lake Mahkeenac

Cozy Cabin on Lake Mahkeenac

2 beds 1 bath
PoolA/CWiFiBalcony
$235/night
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Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

4 beds 3 baths
PoolA/CWiFiBalcony
$442/night
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A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

6 beds 6 baths
PoolA/CWiFiBalcony
$1,001/night
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Stockbridge Retreat w/ Pool & Hot Tub!

Stockbridge Retreat w/ Pool & Hot Tub!

4 beds 3 baths
PoolA/CWiFiBalcony
$1,095/night
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Fabulous In-town Stockbridge Pied-á-Terre, pet friendly!

Fabulous In-town Stockbridge Pied-á-Terre, pet friendly!

1 bed 1 bath
PoolA/CWiFiBalcony
$250/night
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Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge

3 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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A Charming Mid 1800's Stockbridge Farmhouse.

A Charming Mid 1800's Stockbridge Farmhouse.

4 beds 2 baths
PoolA/CWiFiBalcony
$300/night
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Classic Stockbridge Cottage

Classic Stockbridge Cottage

4 beds 2 baths
PoolA/CWiFiBalcony
$298/night
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Modern Cottage in the heart of the Berkshires with new exterior flex space!

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

3 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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Find your Sanctuary at The Rectory at Stockbridge

Find your Sanctuary at The Rectory at Stockbridge

5 beds 2 baths
PoolA/CWiFiBalcony
$839/night
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Cozy Stockbridge Cabin - Walk to Beach & Lake!

Cozy Stockbridge Cabin - Walk to Beach & Lake!

2 beds 2 baths
PoolA/CWiFiBalcony
$338/night
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Two Blocks from the Red Lion Inn & next to Berkshire Theater

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

3 beds 2 baths
PoolA/CWiFiBalcony
$300/night
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Gracious Berkshire Retreat

Gracious Berkshire Retreat

3 beds 2 baths
PoolA/CWiFiBalcony
$526/night
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