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Stockbridge Holiday Apartments

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23 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!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A Grand Estate in Historic Stockbridge, holiday rental in Stockbridge

A Grand Estate in Historic Stockbridge

6 bedrooms
8 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

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse

4 bedrooms
2 bathrooms
Sleeps 4
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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family-friendly Cottage Near Lake, Tanglewood, holiday rental in Stockbridge

Family-friendly Cottage Near Lake, Tanglewood

3 bedrooms
2 bathrooms
Sleeps 7
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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tranquil 3BR Stockbridge House w/Private Deck, holiday rental in Stockbridge

Tranquil 3BR Stockbridge House w/Private Deck

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

2 bedrooms
2 bathrooms
Sleeps 4
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

3 bedrooms
2 bathrooms
Sleeps 6
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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rabbit Run - in the heart of Stockbridge, holiday rental in Stockbridge

Rabbit Run - in the heart of Stockbridge

3 bedrooms
2 bathrooms
Sleeps 7
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

3 bedrooms
2 bathrooms
Sleeps 5
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Stockbridge renovated classic- picture perfect, holiday rental in Stockbridge

Stockbridge renovated classic- picture perfect

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

Iris Room

1 bedroom
1 bathroom
Sleeps 2
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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'Too Good' AKA 2 Goodrich St., holiday rental in Stockbridge

'Too Good' AKA 2 Goodrich St.

4 bedrooms
4 bathrooms
Sleeps 12
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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

3 bedrooms
2 bathrooms
Sleeps 6
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Horse Room, holiday rental in Stockbridge

Horse Room

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, holiday rental in Stockbridge

CABIN FEVER IN STOCKBRIDGE

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in Stockbridge

Stockbridge Bowl Lake Community

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in Stockbridge

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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