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West Stockbridge Rentals

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West Stockbridge Rentals

176 Houses

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$250

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Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 34 minutes

Price per night from

$100

1 / 8

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$325

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Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits

Price per night from

$274

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'Butterfly Hill' West Stockbridge Home on 3 Acres!

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 17 minutes

Price per night from

$165

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Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 12

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l

Price per night from

$260

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Beautifully Renovated Berkshires Farmhouse

West Stockbridge b and b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$210

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Great rentals within 20 miles that match your search

3BR Lee House w/ Easy Access to Main Street!

Lee house

1 bedroom / 2 bathrooms / sleeps 10

Responds fast! avg. 46 minutes

Price per night from

$239

1 / 24

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$299

1 / 31

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$225

1 / 14

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

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Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$274

1 / 20

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are

Price per night from

$149

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Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$448

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2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope

Price per night from

$224

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NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 0 minutes

Price per night from

$375

1 / 24

Berkshire Country Estate - The Library Suite

Old Chatham house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$150

1 / 21

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 51 minutes

Price per night from

$420

1 / 24

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

Price per night from

$125

1 / 6

Berkshires Cottage Country Retreat

Stephentown cottage

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$165

1 / 7

3BD Newly Rennovated Contempoary Near Stockbridge

Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$299

1 / 26

Jiminy Peak Luxury Ski In/Ski Out Home

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$389

1 / 13

Olde York Farm Distillery Suite

Claverack farmhouse

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$250

1 / 16

Roaring Rapids Cottage

Columbiaville house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$250

1 / 16

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$145

1 / 16

Writer's Room at Chestnut Lodge

Lee b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 45 minutes

Price per night from

$175

1 / 8

the BIG room at chestnut lodge

Lee b and b

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 45 minutes

Price per night from

$200

1 / 7

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$750

1 / 22

Cozy Copake Lake Cottage

Copake house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$107

1 / 4

Overnight at Althouse -Higgins

Hillsdale apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$175

1 / 11

House share/room for rent

Lee room

1 bedroom / 1 bathroom / sleeps 1

Price per night from

$67

1 / 15

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$150

1 / 4

Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 55 minutes

Price per night from

$209

1 / 24

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$175

1 / 13

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$170

1 / 19

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$2,489

1 / 4

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 28 minutes

Price per night from

$150

1 / 14

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$150

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