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West Stockbridge Vacation Rentals

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50 rentals in West Stockbridge.
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4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., vacation rental in West Stockbridge
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., vacation rental in West Stockbridge
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town., vacation rental in West Stockbridge

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vacation in a  Berkshire Farmhouse, vacation rental in West Stockbridge
Vacation in a  Berkshire Farmhouse, vacation rental in West Stockbridge
Vacation in a  Berkshire Farmhouse, vacation rental in West Stockbridge

Vacation in a Berkshire Farmhouse

Rental Home
5 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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CHARMING, Large Fireplace, VIEWS For Miles, Come RELAX, vacation rental in West Stockbridge
CHARMING, Large Fireplace, VIEWS For Miles, Come RELAX, vacation rental in West Stockbridge
CHARMING, Large Fireplace, VIEWS For Miles, Come RELAX, vacation rental in West Stockbridge

CHARMING, Large Fireplace, VIEWS For Miles, Come RELAX

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Berkshire Farmhouse Vacation, vacation rental in West Stockbridge
Berkshire Farmhouse Vacation, vacation rental in West Stockbridge
Berkshire Farmhouse Vacation, vacation rental in West Stockbridge

Berkshire Farmhouse Vacation

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

Charming Farmhouse Steps from Downtown West Stockbridge

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood), vacation rental in West Stockbridge
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood), vacation rental in West Stockbridge
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood), vacation rental in West Stockbridge

Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, vacation rental in West Stockbridge
Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, vacation rental in West Stockbridge
Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires, vacation rental in West Stockbridge

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tranquil Berkshires Retreat, vacation rental in West Stockbridge
Tranquil Berkshires Retreat, vacation rental in West Stockbridge
Tranquil Berkshires Retreat, vacation rental in West Stockbridge

Tranquil Berkshires Retreat

Rental Home
6 bedrooms
7 bathrooms
Sleeps 11
Match: Sleeps
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Mountain View, Minutes from Tanglewood, vacation rental in West Stockbridge
Mountain View, Minutes from Tanglewood, vacation rental in West Stockbridge
Mountain View, Minutes from Tanglewood, vacation rental in West Stockbridge

Mountain View, Minutes from Tanglewood

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views, vacation rental in West Stockbridge
Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views, vacation rental in West Stockbridge
Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views, vacation rental in West Stockbridge

Private, Mountain Retreat with Indoor Pool and Fantastic Westward Mountain Views

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, vacation rental in West Stockbridge
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, vacation rental in West Stockbridge
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood, vacation rental in West Stockbridge

Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in West Stockbridge
Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in West Stockbridge
Spring Break Special!  Stay two nights get one free for March and April!, vacation rental in West Stockbridge

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

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

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

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

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Warm your heart this holiday season in this cozy cottage next to downtown Lenox., vacation rental in West Stockbridge
Warm your heart this holiday season in this cozy cottage next to downtown Lenox., vacation rental in West Stockbridge
Warm your heart this holiday season in this cozy cottage next to downtown Lenox., vacation rental in West Stockbridge

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

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

A Grand Estate in Historic Stockbridge

Rental Home
6 bedrooms
8 bathrooms
Sleeps 12
Match: Sleeps
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General Williams Estate House Lenox/Stockbridge, vacation rental in West Stockbridge
General Williams Estate House Lenox/Stockbridge, vacation rental in West Stockbridge
General Williams Estate House Lenox/Stockbridge, vacation rental in West 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 West Stockbridge
Spectacular Housatonic River View from newly renovated Historic Cottage, vacation rental in West Stockbridge
Spectacular Housatonic River View from newly renovated Historic Cottage, vacation rental in West Stockbridge

Spectacular Housatonic River View from newly renovated Historic Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, vacation rental in West Stockbridge
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, vacation rental in West Stockbridge
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood, vacation rental in West Stockbridge

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in West Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in West Stockbridge
A Charming Mid 1800's Stockbridge Farmhouse, vacation rental in West Stockbridge

A Charming Mid 1800's Stockbridge Farmhouse

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hidden Gem in Lenox Great Estate / Handicap Accessible, vacation rental in West Stockbridge
Hidden Gem in Lenox Great Estate / Handicap Accessible, vacation rental in West Stockbridge
Hidden Gem in Lenox Great Estate / Handicap Accessible, vacation rental in West Stockbridge

Hidden Gem in Lenox Great Estate / Handicap Accessible

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Historical  Downtown 1bedroom, vacation rental in West Stockbridge
Historical  Downtown 1bedroom, vacation rental in West Stockbridge
Historical  Downtown 1bedroom, vacation rental in West Stockbridge

Historical Downtown 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Renovated Downtown 1bedroom, vacation rental in West Stockbridge
Renovated Downtown 1bedroom, vacation rental in West Stockbridge
Renovated Downtown 1bedroom, vacation rental in West Stockbridge

Renovated Downtown 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, vacation rental in West Stockbridge
Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, vacation rental in West Stockbridge
Charming Stockbridge Historic Victorian  a StoneThrow Away from the Red Lion INN, vacation rental in West Stockbridge

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

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

Peaceful Woodland Home in the Heart of the Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, vacation rental in West Stockbridge
Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, vacation rental in West Stockbridge
Excellent WiFi|Labor Day FALL Winter |The Escape at STOCKBRIDGE|The BERKSHIRES, vacation rental in West Stockbridge

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Beautifully Restored 1820s Industrial Loft Living On A Creek, vacation rental in West Stockbridge
Beautifully Restored 1820s Industrial Loft Living On A Creek, vacation rental in West Stockbridge
Beautifully Restored 1820s Industrial Loft Living On A Creek, vacation rental in West Stockbridge

Beautifully Restored 1820s Industrial Loft Living On A Creek

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, vacation rental in West Stockbridge
Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, vacation rental in West Stockbridge
Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats, vacation rental in West Stockbridge

Walk to Tanglewood -Luxury Dream Home - Htd Pool, Hot Tub, Stckbrdg Bowl w/Boats

Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
More info
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Stockbridge Bowl Lake Community, vacation rental in West Stockbridge
Stockbridge Bowl Lake Community, vacation rental in West Stockbridge
Stockbridge Bowl Lake Community, vacation rental in West Stockbridge

Stockbridge Bowl Lake Community

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in West Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in West Stockbridge
Sophisticated &  Comfortable Stockbridge Retreat  A+ Location  Modern Amenities, vacation rental in West Stockbridge

Sophisticated & Comfortable Stockbridge Retreat A+ Location Modern Amenities

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

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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CABIN FEVER IN STOCKBRIDGE, vacation rental in West Stockbridge
CABIN FEVER IN STOCKBRIDGE, vacation rental in West Stockbridge
CABIN FEVER IN STOCKBRIDGE, vacation rental in West Stockbridge

CABIN FEVER IN STOCKBRIDGE

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Artist's Cottage on the Lake Mahkeenac, vacation rental in West Stockbridge
Artist's Cottage on the Lake Mahkeenac, vacation rental in West Stockbridge
Artist's Cottage on the Lake Mahkeenac, vacation rental in West Stockbridge

Artist's Cottage on the Lake Mahkeenac

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, vacation rental in West Stockbridge
NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, vacation rental in West Stockbridge
NEW! Cozy Berkshires Cabin - Walk to Beach & Lake!, vacation rental in West Stockbridge

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - The Lodge's Campsite, vacation rental in West Stockbridge
Tentrr Signature Site - The Lodge's Campsite, vacation rental in West Stockbridge
Tentrr Signature Site - The Lodge's Campsite, vacation rental in West Stockbridge

Tentrr Signature Site - The Lodge's Campsite

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, vacation rental in West Stockbridge
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, vacation rental in West Stockbridge
LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE, vacation rental in West Stockbridge

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Fox Hollow Laurel Lake Ranch, vacation rental in West Stockbridge
Fox Hollow Laurel Lake Ranch, vacation rental in West Stockbridge
Fox Hollow Laurel Lake Ranch, vacation rental in West Stockbridge

Fox Hollow Laurel Lake Ranch

Rental Home
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Vacation Home on 10 Acres with Pool and Spa, vacation rental in West Stockbridge
Vacation Home on 10 Acres with Pool and Spa, vacation rental in West Stockbridge
Vacation Home on 10 Acres with Pool and Spa, vacation rental in West Stockbridge

Vacation Home on 10 Acres with Pool and Spa

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Iris Room, vacation rental in West Stockbridge
Iris Room, vacation rental in West Stockbridge
Iris Room, vacation rental in West Stockbridge

Iris Room

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

Horse Room

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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September  availability -Stunning secluded elegance in parklike setting, vacation rental in West Stockbridge
September  availability -Stunning secluded elegance in parklike setting, vacation rental in West Stockbridge
September  availability -Stunning secluded elegance in parklike setting, vacation rental in West Stockbridge

September availability -Stunning secluded elegance in parklike setting

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
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One of the Finest Homes and Best location in the Berkshires, vacation rental in West Stockbridge
One of the Finest Homes and Best location in the Berkshires, vacation rental in West Stockbridge
One of the Finest Homes and Best location in the Berkshires, vacation rental in West Stockbridge

One of the Finest Homes and Best location in the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, vacation rental in West Stockbridge
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, vacation rental in West Stockbridge
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA, vacation rental in West Stockbridge

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in West Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in West Stockbridge
Cozy cottage minutes away from  Tanglewood and Stockbridge center, vacation rental in West 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 West Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, vacation rental in West Stockbridge
Berkshire Condo - Walk To Tanglewood & Private Beach On The Stockbridge Bowl, vacation rental in West Stockbridge

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

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Lovely Lenox Home on Bishop Estate.....Walk to Town, Tanglewood, vacation rental in West Stockbridge
Lovely Lenox Home on Bishop Estate.....Walk to Town, Tanglewood, vacation rental in West Stockbridge
Lovely Lenox Home on Bishop Estate.....Walk to Town, Tanglewood, vacation rental in West Stockbridge

Lovely Lenox Home on Bishop Estate.....Walk to Town, Tanglewood

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Berkshire Mountain Hideaway -house, vacation rental in West Stockbridge
Berkshire Mountain Hideaway -house, vacation rental in West Stockbridge
Berkshire Mountain Hideaway -house, vacation rental in West Stockbridge

Berkshire Mountain Hideaway -house

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Best of the Berkshires & Hudson Valley, vacation rental in West Stockbridge
Best of the Berkshires & Hudson Valley, vacation rental in West Stockbridge
Best of the Berkshires & Hudson Valley, vacation rental in West Stockbridge

Best of the Berkshires & Hudson Valley

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious Contemporary With Beautiful Gardens, vacation rental in West Stockbridge
Spacious Contemporary With Beautiful Gardens, vacation rental in West Stockbridge
Spacious Contemporary With Beautiful Gardens, vacation rental in West Stockbridge

Spacious Contemporary With Beautiful Gardens

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in West Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in West Stockbridge
Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh, vacation rental in West Stockbridge

Walk To Tanglewood, Stockbridge Bowl Lake, Wheatleigh

Rental Home
3 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Frequently Asked Questions about West Stockbridge