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West Stockbridge Holiday Rentals

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50 rentals in West Stockbridge.
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Berkshire Farmhouse Vacation, holiday rental in West Stockbridge

Berkshire Farmhouse Vacation

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., holiday rental in West Stockbridge

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

4 bedrooms
2 bathrooms
Sleeps 10
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Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat, holiday rental in West Stockbridge

Newly Renovated 1910 Farmhouse - Walk To Town - Perfect Berkshire Retreat

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, holiday rental in West Stockbridge

Vacation in a Berkshire Farmhouse

5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Charming Farmhouse Steps from Downtown West Stockbridge, holiday rental in West Stockbridge

Charming Farmhouse Steps from Downtown West Stockbridge

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, holiday rental in West Stockbridge

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

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Stockbridge Cabin - Walk to Beach & Lake!, holiday rental in West Stockbridge

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spring Break Special!  Stay two nights get one free for March and April!, holiday rental in West 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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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., holiday rental in West Stockbridge

Warm your heart this holiday season in this cozy cottage next to downtown Lenox.

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A Grand Estate in Historic Stockbridge, holiday rental in West Stockbridge

A Grand Estate in Historic Stockbridge

6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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RANKED #1 for 5 STAR REVIEWS covering 355 properties., holiday rental in West Stockbridge

RANKED #1 for 5 STAR REVIEWS covering 355 properties.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, holiday rental in West Stockbridge

General Williams Estate House Lenox/Stockbridge

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, holiday rental in West Stockbridge

Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Gartner House, a charming home in Lenox, holiday rental in West Stockbridge

Gartner House, a charming home in Lenox

4 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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A Charming Mid 1800's Stockbridge Farmhouse, holiday rental in West Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse

4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Heart of Lenox Walk to Town Cozy Cottage!, holiday rental in West Stockbridge

Heart of Lenox Walk to Town Cozy Cottage!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Peaceful Woodland Home in the Heart of the Berkshires, holiday rental in West Stockbridge

Peaceful Woodland Home in the Heart of the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cabin on forest road, holiday rental in West Stockbridge

Cabin on forest road

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

Beautifully Restored 1820s Industrial Loft Living On A Creek

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 West Stockbridge

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

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

Rabbit Run - in the heart of Stockbridge

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Holiday in Norman Rockwell's Stockbridge, holiday rental in West Stockbridge

Holiday in Norman Rockwell's Stockbridge

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Family-friendly Cottage Near Lake, Tanglewood, holiday rental in West Stockbridge

Family-friendly Cottage Near Lake, Tanglewood

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, holiday rental in West Stockbridge

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Morning Face - Berkshire estate with heated pool, views and privacy., holiday rental in West Stockbridge

Morning Face - Berkshire estate with heated pool, views and privacy.

4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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CABIN FEVER IN STOCKBRIDGE, holiday rental in West 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 West Stockbridge

Artist's Cottage on the Lake Mahkeenac

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil 3BR Stockbridge House w/Private Deck, holiday rental in West Stockbridge

Tranquil 3BR Stockbridge House w/Private Deck

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House, holiday rental in West Stockbridge

Lake House

5 bedrooms
6 bathrooms
Sleeps 9
Match: Sleeps
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Heart of Lenox, holiday rental in West Stockbridge

Heart of Lenox

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Stockbridge Bowl Lake Community, holiday rental in West Stockbridge

Stockbridge Bowl Lake Community

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, holiday rental in West Stockbridge

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Newly Renovated Colonial on the River! Sleeps 5-6, holiday rental in West Stockbridge

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 West Stockbridge

Stockbridge renovated classic- picture perfect

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Fox Hollow Laurel Lake Ranch, holiday rental in West Stockbridge

Fox Hollow Laurel Lake Ranch

4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Berkshires Home w/Kayak - Walk to Stockbridge Bowl, holiday rental in West Stockbridge

Berkshires Home w/Kayak - Walk to Stockbridge Bowl

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

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 West Stockbridge

Iris Room

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

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 West Stockbridge

One of the Finest Homes and Best location in the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Private Guest House in Dtwn Lenox, Walk to Dining!, holiday rental in West Stockbridge

Private Guest House in Dtwn Lenox, Walk to Dining!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, holiday rental in West Stockbridge

Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!, holiday rental in West Stockbridge

Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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'Too Good' AKA 2 Goodrich St., holiday rental in West Stockbridge

'Too Good' AKA 2 Goodrich St.

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Restored 1881 Farm House, holiday rental in West Stockbridge

Restored 1881 Farm House

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Berkshire Mountain Hideaway, holiday rental in West Stockbridge

Tentrr Signature Site - Berkshire Mountain Hideaway

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - The Lodge's Campsite, holiday rental in West Stockbridge

Tentrr Signature Site - The Lodge's Campsite

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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** Private Berkshire Escape** Monthly Pricing Available, holiday rental in West Stockbridge

** Private Berkshire Escape** Monthly Pricing Available

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Contemporary With Beautiful Gardens, holiday rental in West Stockbridge

Spacious Contemporary With Beautiful Gardens

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, holiday rental in West Stockbridge

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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