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Housatonic Holiday Rentals

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50 rentals in Housatonic.
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!, holiday rental in Housatonic

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

4 bedrooms
2 bathrooms
Sleeps 10
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Spacious Contemporary With Beautiful Gardens, holiday rental in Housatonic

Spacious Contemporary With Beautiful Gardens

4 bedrooms
4 bathrooms
Sleeps 8
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Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in Housatonic

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

3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful 1920's Colonial 20 Minutes from Tanglewood, holiday rental in Housatonic

Beautiful 1920's Colonial 20 Minutes from Tanglewood

4 bedrooms
2 bathrooms
Sleeps 8
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The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!, holiday rental in Housatonic

The perfect getaway: 5 bd, 3 ba, 3 acres. Booking for fall, winter & 2021!

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Downtown GB apartment walk to shops and restaurants, holiday rental in Housatonic

Downtown GB apartment walk to shops and restaurants

2 bedrooms
1 bathroom
Sleeps 5
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in Housatonic

4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.

4 bedrooms
2 bathrooms
Sleeps 10
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A Grand Estate in Historic Stockbridge, holiday rental in Housatonic

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 Housatonic

General Williams Estate House Lenox/Stockbridge

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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2 bedroom Riverhouse in the Heart of the Berkshires, holiday rental in Housatonic

2 bedroom Riverhouse in the Heart of the Berkshires

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, holiday rental in Housatonic

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Stunning Renovated Victorian, holiday rental in Housatonic

Stunning Renovated Victorian

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Charming, Quiet, Modern, Wooded, River Front, holiday rental in Housatonic

Charming, Quiet, Modern, Wooded, River Front

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Beautiful home with all amenities. Close to everything. Fiber optic internet., holiday rental in Housatonic

Beautiful home with all amenities. Close to everything. Fiber optic internet.

2 bedrooms
2 bathrooms
Sleeps 4
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Berkshire Farmhouse Vacation, holiday rental in Housatonic

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Berkshires: Romantic Cottage with spectacular view, holiday rental in Housatonic

Berkshires: Romantic Cottage with spectacular view

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in Housatonic

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in Housatonic

A Charming Mid 1800's Stockbridge Farmhouse

4 bedrooms
2 bathrooms
Sleeps 4
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Quiet Guest House In The Green River Valley, holiday rental in Housatonic

Quiet Guest House In The Green River Valley

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Two Rooms with En-Suite in Quiet Woodland, holiday rental in Housatonic

Two Rooms with En-Suite in Quiet Woodland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW SECLUDED 3 BEDROOM COUNTRY CASTLE, holiday rental in Housatonic

NEW SECLUDED 3 BEDROOM COUNTRY CASTLE

3 bedrooms
3 bathrooms
Sleeps 6
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Barn Apartment in Gorgeous Stonybrook Farm, holiday rental in Housatonic

Barn Apartment in Gorgeous Stonybrook Farm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautifully Restored 1820s Industrial Loft Living On A Creek, holiday rental in Housatonic

Beautifully Restored 1820s Industrial Loft Living On A Creek

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Case Mill-Secluded Berkshire farmhouse, mill, pond, waterfall, 28 acre forest., holiday rental in Housatonic

Case Mill-Secluded Berkshire farmhouse, mill, pond, waterfall, 28 acre forest.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington, holiday rental in Housatonic

Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Rabbit Run - in the heart of Stockbridge, holiday rental in Housatonic

Rabbit Run - in the heart of Stockbridge

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Two Blocks from the Red Lion Inn & next to Berkshire Theater, holiday rental in Housatonic

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

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

Holiday in Norman Rockwell's Stockbridge

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, holiday rental in Housatonic

Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in Housatonic

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Upscale Country Cottage, holiday rental in Housatonic

Upscale Country Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gem of the Berkshires, walk to downtown & lake., holiday rental in Housatonic

Gem of the Berkshires, walk to downtown & lake.

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Modern Victorian on the Hill, holiday rental in Housatonic

Modern Victorian on the Hill

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tranquil 3BR Stockbridge House w/Private Deck, holiday rental in Housatonic

Tranquil 3BR Stockbridge House w/Private Deck

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in Housatonic

Stockbridge Bowl Lake Community

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront Berkshires Ski/Summer House, Great Views, holiday rental in Housatonic

Lakefront Berkshires Ski/Summer House, Great Views

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Hillhouse Log Cabin, holiday rental in Housatonic

Hillhouse Log Cabin

3 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in Housatonic

Newly Renovated Colonial on the River! Sleeps 5-6

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

Stockbridge renovated classic- picture perfect

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Eco-friendly cozy home in Gt. Barrington, holiday rental in Housatonic

Eco-friendly cozy home in Gt. Barrington

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tanglewood / Berkshires - 2 Bed 2 Bath Apartment, holiday rental in Housatonic

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Vacation Home on 10 Acres with Pool and Spa, holiday rental in Housatonic

Vacation Home on 10 Acres with Pool and Spa

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Iris Room, holiday rental in Housatonic

Iris Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Horse Room, holiday rental in Housatonic

Horse Room

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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One of the Finest Homes and Best location in the Berkshires, holiday rental in Housatonic

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 Housatonic

'Too Good' AKA 2 Goodrich St.

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Impeccable House Minutes from Downtown Great Barrington, holiday rental in Housatonic

Impeccable House Minutes from Downtown Great Barrington

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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** Private Berkshire Escape** Monthly Pricing Available, holiday rental in Housatonic

** Private Berkshire Escape** Monthly Pricing Available

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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NEW! Serene Great Barrington Cottage w/ Fire Pit!, holiday rental in Housatonic

NEW! Serene Great Barrington Cottage w/ Fire Pit!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!, holiday rental in Housatonic

Tentrr Signature Site - Great Barrington Campsite - with Goats and Pool!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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