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Stockbridge Apartments

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47 rentals in Stockbridge.
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Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in Stockbridge
Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in Stockbridge
Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in Stockbridge

Spring Break Special! Stay two nights get one free for March and April!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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STOCKBRIDGE  One Of The Finest Homes and Best Locations... Walk To Beach, vacation rental in Stockbridge
STOCKBRIDGE  One Of The Finest Homes and Best Locations... Walk To Beach, vacation rental in Stockbridge
STOCKBRIDGE  One Of The Finest Homes and Best Locations... Walk To Beach, vacation rental in Stockbridge

STOCKBRIDGE One Of The Finest Homes and Best Locations... Walk To Beach

Rental Home
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, vacation rental in Stockbridge
Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, vacation rental in Stockbridge
Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, vacation rental in Stockbridge

Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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A Grand Estate in Historic Stockbridge, vacation rental in Stockbridge
A Grand Estate in Historic Stockbridge, vacation rental in Stockbridge
A Grand Estate in Historic Stockbridge, vacation rental in Stockbridge

A Grand Estate in Historic Stockbridge

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Stockbridge! 1/2 mile from Red Lion inn.  Great Barrington, Lenox, Lee close by., vacation rental in Stockbridge
Stockbridge! 1/2 mile from Red Lion inn.  Great Barrington, Lenox, Lee close by., vacation rental in Stockbridge
Stockbridge! 1/2 mile from Red Lion inn.  Great Barrington, Lenox, Lee close by., vacation rental in Stockbridge

Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox, Lee close by.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, vacation rental in Stockbridge
General Williams Estate House Lenox/Stockbridge, vacation rental in Stockbridge
General Williams Estate House Lenox/Stockbridge, vacation rental in Stockbridge

General Williams Estate House Lenox/Stockbridge

Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Spectacular Housatonic River View from newly renovated Historic Cottage, vacation rental in Stockbridge
Spectacular Housatonic River View from newly renovated Historic Cottage, vacation rental in Stockbridge
Spectacular Housatonic River View from newly renovated Historic Cottage, vacation rental in Stockbridge

Spectacular Housatonic River View from newly renovated Historic Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, vacation rental in Stockbridge
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, vacation rental in Stockbridge
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, vacation rental in Stockbridge

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Colonial on the River! Fantastic Views, vacation rental in Stockbridge
Renovated Colonial on the River! Fantastic Views, vacation rental in Stockbridge
Renovated Colonial on the River! Fantastic Views, vacation rental in Stockbridge

Renovated Colonial on the River! Fantastic Views

Rental Home
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse

Rental Home
4 bedrooms
5 bathrooms
Sleeps 4
Match: Sleeps
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In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing, vacation rental in Stockbridge
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing, vacation rental in Stockbridge
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing, vacation rental in Stockbridge

In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing

Rental Home
12 bedrooms
13 bathrooms
Sleeps 24
Match: Sleeps
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Peaceful Woodland Home in the Heart of the Berkshires, vacation rental in Stockbridge
Peaceful Woodland Home in the Heart of the Berkshires, vacation rental in Stockbridge
Peaceful Woodland Home in the Heart of the Berkshires, vacation rental in Stockbridge

Peaceful Woodland Home in the Heart of the Berkshires

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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ESCAPE to STOCKBRIDGE|TANGLEWOOD|The BERKSHIRES|, vacation rental in Stockbridge
ESCAPE to STOCKBRIDGE|TANGLEWOOD|The BERKSHIRES|, vacation rental in Stockbridge
ESCAPE to STOCKBRIDGE|TANGLEWOOD|The BERKSHIRES|, vacation rental in Stockbridge

ESCAPE to STOCKBRIDGE|TANGLEWOOD|The BERKSHIRES|

Rental Home
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Stockbridge Cottage minutes from downtown Lenox, vacation rental in Stockbridge
Stockbridge Cottage minutes from downtown Lenox, vacation rental in Stockbridge
Stockbridge Cottage minutes from downtown Lenox, vacation rental in Stockbridge

Stockbridge Cottage minutes from downtown Lenox

Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Rabbit Run - 5 minute walk to Stockbridge Village

Rental Home
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Artist's Camp on Lake Mahkeenac, vacation rental in Stockbridge
Artist's Camp on Lake Mahkeenac, vacation rental in Stockbridge
Artist's Camp on Lake Mahkeenac, vacation rental in Stockbridge

Artist's Camp on Lake Mahkeenac

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stockbridge Bowl Lake Community, vacation rental in Stockbridge
Stockbridge Bowl Lake Community, vacation rental in Stockbridge
Stockbridge Bowl Lake Community, vacation rental in Stockbridge

Stockbridge Bowl Lake Community

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Two Blocks from the Red Lion Inn & next to Berkshire Theater, vacation rental in Stockbridge
Two Blocks from the Red Lion Inn & next to Berkshire Theater, vacation rental in Stockbridge
Two Blocks from the Red Lion Inn & next to Berkshire Theater, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Holiday in Norman Rockwell's Stockbridge, vacation rental in Stockbridge
Holiday in Norman Rockwell's Stockbridge, vacation rental in Stockbridge
Holiday in Norman Rockwell's Stockbridge, vacation rental in Stockbridge

Holiday in Norman Rockwell's Stockbridge

Rental Home
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in Stockbridge

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, vacation rental in Stockbridge
CABIN FEVER IN STOCKBRIDGE, vacation rental in Stockbridge
CABIN FEVER IN STOCKBRIDGE, vacation rental in Stockbridge

CABIN FEVER IN STOCKBRIDGE

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Stockbridge Cabin - Walk to Beach & Lake!, vacation rental in Stockbridge
Cozy Stockbridge Cabin - Walk to Beach & Lake!, vacation rental in Stockbridge
Cozy Stockbridge Cabin - Walk to Beach & Lake!, vacation rental in Stockbridge

Cozy Stockbridge Cabin - Walk to Beach & Lake!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Colonial on the River! Sleeps 5-6, vacation rental in Stockbridge
Newly Renovated Colonial on the River! Sleeps 5-6, vacation rental in Stockbridge
Newly Renovated Colonial on the River! Sleeps 5-6, vacation rental in Stockbridge

Newly Renovated Colonial on the River! Sleeps 5-6

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., vacation rental in Stockbridge
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., vacation rental in Stockbridge
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., vacation rental in Stockbridge

Circa 1900 Berkshire Cottage on 75 acres. Very private yet centrally located.

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Walk into town, soak up sun on enclosed porch & steps away from nature trails, vacation rental in Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails, vacation rental in Stockbridge
Walk into town, soak up sun on enclosed porch & steps away from nature trails, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Cabin on Lake Mahkeenac, vacation rental in Stockbridge
Cozy Cabin on Lake Mahkeenac, vacation rental in Stockbridge
Cozy Cabin on Lake Mahkeenac, vacation rental in Stockbridge

Cozy Cabin on Lake Mahkeenac

Rental Home
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in Stockbridge

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Rental Home
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Stockbridge renovated classic- picture perfect, vacation rental in Stockbridge
Stockbridge renovated classic- picture perfect, vacation rental in Stockbridge
Stockbridge renovated classic- picture perfect, vacation rental in Stockbridge

Stockbridge renovated classic- picture perfect

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Iris Room, vacation rental in Stockbridge
Iris Room, vacation rental in Stockbridge
Iris Room, vacation rental in Stockbridge

Iris Room

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Horse Room, vacation rental in Stockbridge
Horse Room, vacation rental in Stockbridge
Horse Room, vacation rental in Stockbridge

Horse Room

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, vacation rental in Stockbridge
One of the Finest Homes and Best location in the Berkshires, vacation rental in Stockbridge
One of the Finest Homes and Best location in the Berkshires, vacation rental in Stockbridge

One of the Finest Homes and Best location in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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"Too Good" AKA 2 Goodrich St., vacation rental in Stockbridge
"Too Good" AKA 2 Goodrich St., vacation rental in Stockbridge
"Too Good" AKA 2 Goodrich St., vacation rental in Stockbridge

"Too Good" AKA 2 Goodrich St.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, vacation rental in Stockbridge
Vacation Home on 10 Acres with Pool and Spa, vacation rental in Stockbridge
Vacation Home on 10 Acres with Pool and Spa, vacation rental in Stockbridge

Vacation Home on 10 Acres with Pool and Spa

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant & private  light filled 1 level, Full season rental, vacation rental in Stockbridge
Elegant & private  light filled 1 level, Full season rental, vacation rental in Stockbridge
Elegant & private  light filled 1 level, Full season rental, vacation rental in Stockbridge

Elegant & private light filled 1 level, Full season rental

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Tranquil 3BR Stockbridge House w/ Private Deck!, vacation rental in Stockbridge
Tranquil 3BR Stockbridge House w/ Private Deck!, vacation rental in Stockbridge
Tranquil 3BR Stockbridge House w/ Private Deck!, vacation rental in Stockbridge

Tranquil 3BR Stockbridge House w/ Private Deck!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Completely Renovated Historic Home in the Heart of the Berkshires

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in Stockbridge

Cozy cottage minutes away from Tanglewood and Stockbridge center

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, vacation rental in Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, vacation rental in Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, vacation rental in Stockbridge

Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stockbridge Estate with Mountain Views, vacation rental in Stockbridge
Stockbridge Estate with Mountain Views, vacation rental in Stockbridge
Stockbridge Estate with Mountain Views, vacation rental in Stockbridge

Stockbridge Estate with Mountain Views

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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One block from Main St Stockbridge, vacation rental in Stockbridge
One block from Main St Stockbridge, vacation rental in Stockbridge
One block from Main St Stockbridge, vacation rental in Stockbridge

One block from Main St Stockbridge

Rental Home
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Historic Stockbridge Villa on 25 acres sleeps 23, vacation rental in Stockbridge
Historic Stockbridge Villa on 25 acres sleeps 23, vacation rental in Stockbridge
Historic Stockbridge Villa on 25 acres sleeps 23, vacation rental in Stockbridge

Historic Stockbridge Villa on 25 acres sleeps 23

Rental Home
12 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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Beachwood Cottage, vacation rental in Stockbridge
Beachwood Cottage, vacation rental in Stockbridge
Beachwood Cottage, vacation rental in Stockbridge

Beachwood Cottage

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great house in Stockbridge, vacation rental in Stockbridge
Great house in Stockbridge, vacation rental in Stockbridge
Great house in Stockbridge, vacation rental in Stockbridge

Great house in Stockbridge

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Grand 3Room, Historic Stockbridge, ON Main Street!, vacation rental in Stockbridge
Grand 3Room, Historic Stockbridge, ON Main Street!, vacation rental in Stockbridge
Grand 3Room, Historic Stockbridge, ON Main Street!, vacation rental in Stockbridge

Grand 3Room, Historic Stockbridge, ON Main Street!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Holmes Suite: PRIME Downtown Stockbridge, vacation rental in Stockbridge
Holmes Suite: PRIME Downtown Stockbridge, vacation rental in Stockbridge
Holmes Suite: PRIME Downtown Stockbridge, vacation rental in Stockbridge

Holmes Suite: PRIME Downtown Stockbridge

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic & Charming 2 Bedroom,Downtown Stockbridge, vacation rental in Stockbridge
Historic & Charming 2 Bedroom,Downtown Stockbridge, vacation rental in Stockbridge
Historic & Charming 2 Bedroom,Downtown Stockbridge, vacation rental in Stockbridge

Historic & Charming 2 Bedroom,Downtown Stockbridge

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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NEW! Stockbridge Home - Walk to Lakefront Beach!, vacation rental in Stockbridge
NEW! Stockbridge Home - Walk to Lakefront Beach!, vacation rental in Stockbridge
NEW! Stockbridge Home - Walk to Lakefront Beach!, vacation rental in Stockbridge

NEW! Stockbridge Home - Walk to Lakefront Beach!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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