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Stockbridge Holiday Apartments

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

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

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

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, holiday rental in Stockbridge
Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, holiday rental in Stockbridge
Stockbridge Cape Near Tanglewood & Kripalu - Heart Of The Berkshires!, holiday rental in Stockbridge

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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A Grand Estate in Historic Stockbridge, holiday rental in Stockbridge
A Grand Estate in Historic Stockbridge, holiday rental in Stockbridge
A Grand Estate in Historic Stockbridge, holiday rental in Stockbridge

A Grand Estate in Historic Stockbridge

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

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

Holiday Rental House
0 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, holiday rental in Stockbridge
General Williams Estate House Lenox/Stockbridge, holiday rental in Stockbridge
General Williams Estate House Lenox/Stockbridge, holiday rental in Stockbridge

General Williams Estate House Lenox/Stockbridge

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

Spectacular Housatonic River View from newly renovated Historic Cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Renovated Colonial on the River! Fantastic Views, holiday rental in Stockbridge
Renovated Colonial on the River! Fantastic Views, holiday rental in Stockbridge
Renovated Colonial on the River! Fantastic Views, holiday rental in Stockbridge

Renovated Colonial on the River! Fantastic Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, holiday rental in Stockbridge
Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, holiday rental in Stockbridge
Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, holiday rental in Stockbridge

Charming Stockbridge Historic Victorian a StoneThrow Away from the Red Lion INN

Holiday Rental House
12 bedrooms
8 bathrooms
Sleeps 24
Match: Sleeps
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Peaceful Woodland Home in the Heart of the Berkshires, holiday rental in Stockbridge
Peaceful Woodland Home in the Heart of the Berkshires, holiday rental in Stockbridge
Peaceful Woodland Home in the Heart of the Berkshires, holiday rental in Stockbridge

Peaceful Woodland Home in the Heart of the Berkshires

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, holiday rental in Stockbridge
Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, holiday rental in Stockbridge
Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, holiday rental in Stockbridge

Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Rabbit Run - in the heart of Stockbridge, holiday rental in Stockbridge
Rabbit Run - in the heart of Stockbridge, holiday rental in Stockbridge
Rabbit Run - in the heart of Stockbridge, holiday rental in Stockbridge

Rabbit Run - in the heart of Stockbridge

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Stockbridge
Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Stockbridge
Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Stockbridge

Beautifully Restored 1820s Industrial Loft Living On A Creek

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in Stockbridge
Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in Stockbridge
Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in Stockbridge

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

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

Holiday in Norman Rockwell's Stockbridge

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in Stockbridge
Stockbridge Bowl Lake Community, holiday rental in Stockbridge
Stockbridge Bowl Lake Community, holiday rental in Stockbridge

Stockbridge Bowl Lake Community

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Stockbridge

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, holiday rental in Stockbridge
CABIN FEVER IN STOCKBRIDGE, holiday rental in Stockbridge
CABIN FEVER IN STOCKBRIDGE, holiday rental in Stockbridge

CABIN FEVER IN STOCKBRIDGE

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Artist's Cottage on the Lake Mahkeenac, holiday rental in Stockbridge
Artist's Cottage on the Lake Mahkeenac, holiday rental in Stockbridge
Artist's Cottage on the Lake Mahkeenac, holiday rental in Stockbridge

Artist's Cottage on the Lake Mahkeenac

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, holiday rental in Stockbridge
NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, holiday rental in Stockbridge
NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, holiday rental in Stockbridge

NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in Stockbridge
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in Stockbridge
Circa 1900 Berkshire Cottage on 75 acres.  Very private yet centrally located., holiday rental in Stockbridge

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

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in Stockbridge
Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in Stockbridge
Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in Stockbridge

Newly Renovated Colonial on the River! Sleeps 5-6

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Stockbridge

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, holiday rental in Stockbridge
One of the Finest Homes and Best location in the Berkshires, holiday rental in Stockbridge
One of the Finest Homes and Best location in the Berkshires, holiday rental in Stockbridge

One of the Finest Homes and Best location in the Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Stockbridge renovated classic- picture perfect, holiday rental in Stockbridge
Stockbridge renovated classic- picture perfect, holiday rental in Stockbridge
Stockbridge renovated classic- picture perfect, holiday rental in Stockbridge

Stockbridge renovated classic- picture perfect

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Iris Room, holiday rental in Stockbridge
Iris Room, holiday rental in Stockbridge
Iris Room, holiday rental in Stockbridge

Iris Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, holiday rental in Stockbridge
Vacation Home on 10 Acres with Pool and Spa, holiday rental in Stockbridge
Vacation Home on 10 Acres with Pool and Spa, holiday rental in Stockbridge

Vacation Home on 10 Acres with Pool and Spa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'Too Good' AKA 2 Goodrich St., holiday rental in Stockbridge
'Too Good' AKA 2 Goodrich St., holiday rental in Stockbridge
'Too Good' AKA 2 Goodrich St., holiday rental in Stockbridge

'Too Good' AKA 2 Goodrich St.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Horse Room, holiday rental in Stockbridge
Horse Room, holiday rental in Stockbridge
Horse Room, holiday rental in Stockbridge

Horse Room

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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September  availability -Stunning secluded elegance in parklike setting, holiday rental in Stockbridge
September  availability -Stunning secluded elegance in parklike setting, holiday rental in Stockbridge
September  availability -Stunning secluded elegance in parklike setting, holiday rental in Stockbridge

September availability -Stunning secluded elegance in parklike setting

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Cozy cottage minutes away from  Tanglewood and Stockbridge center, holiday rental in Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, holiday rental in Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, holiday rental in Stockbridge

Cozy cottage minutes away from Tanglewood and Stockbridge center

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, holiday rental in Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, holiday rental in Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, holiday 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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One block from Main St Stockbridge, holiday rental in Stockbridge
One block from Main St Stockbridge, holiday rental in Stockbridge
One block from Main St Stockbridge, holiday rental in Stockbridge

One block from Main St Stockbridge

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Frequently Asked Questions about Stockbridge


Yes, here are some popular holiday rentals in Stockbridge that have internet access:\n\nSee all holiday rentals in Stockbridge on Tripadvisor