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Holiday Houses in West Stockbridge

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139 Holiday homes

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

from £236 / night

£1,365 / week

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

4

Responds fast! avg. 1 hour 34 minutes

from £306 / night

£2,141 / week

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

3

from £95 / night

£800 / week

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

7

Responds fast! avg. 2 hours 17 minutes

from £330 / night

£2,306 / week

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 15

42

from £243 / night

£1,445 - £3,412 / week

Beautifully Renovated Berkshires Farmhouse

West Stockbridge b&b

2 bedrooms / 2 bathrooms / sleeps 4

from £198 / night

£1,381 / week

Great rentals within 20 miles that match your search

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house

5 bedrooms / 3 bathrooms / sleeps 14

1

from £424 / night

£2,639 / week

Luxury Fox Hollow Laurel Lake Ranch

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

1

from £472 / night

£2,828 / week

Horse Room

Stockbridge farmhouse

1 bedroom / 1 bathroom / sleeps 3

from £141 / night

£844 / week

from £558 / night

£3,744 / week

Charming Farmhouse on Magical 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

1

Responds fast! avg. 1 hour 1 minutes

from £371 / night

£2,249 - £2,905 / week

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 42 minutes

from £122 / night

£849 / week

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

Stephentown lodge

4 bedrooms / 2 bathrooms / sleeps 10

7

from £353 / night

£2,467 / week

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

1

from £470 / night

£3,289 / week

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms / 2 bathrooms / sleeps 8

2

from £282 / night

£1,692 - £2,349 / week

Berkshire Country Estate - Rose Suite

Old Chatham villa

2 bedrooms / 1 bathroom / sleeps 4

from £160 / night

£1,118 / week

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

from £282 / night

£2,067 / week

Picturesque 19th century home on 3 private acres

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 7

from £141 / night

£837 / week

Country Retreat w/ Pool Near Hip Hudson, NY

Hudson house

3 bedrooms / 3 bathrooms / sleeps 8

from £376 / night

£2,349 / week

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £2,349 / night

£28,146 / week

Berkshires on the Pond

Becket house

2 bedrooms / 2 bathrooms / sleeps 2

from £118 / night

£799 / week

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

from £564 / night

£3,946 - £5,262 / week

Garfield House

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £165 / night

£799 / week

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

from £188 / night

£1,316 / week

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

4

Responds fast! avg. 3 hours 4 minutes

from £259 / night

£1,130 / week

Turning Point - Family Retreat & Group Getaway

Great Barrington house

7 bedrooms / 8 bathrooms / sleeps 15

from £753 / night

£3,765 / week

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / sleeps 4

from £216 / night

£1,506 / week

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

1

from £236 / night

£1,412 / week

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

Hancock house

4 bedrooms / 2 bathrooms / sleeps 9

3

from £212 / night

£1,036 / week

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

from £402 / night

£2,815 / week

Cozy and clean in Gt Barrington- available for October

Great Barrington house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £142 / night

£942 / week

Charming Private Guest Suite in Historic Village in the Berkshires

New Marlborough studio

Studio / 1 bathroom / sleeps 2

from £90 / night

£626 / week

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

33

from £189 / night

£1,130 / week

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

2

from £353 / night

£2,471 - £2,965 / week

Cedar Chest

Canaan cottage

1 bedroom / 1 bathroom / sleeps 2

from £95 / night

£659 / week

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

from £168 / night

£1,177 / week

from £937 / night

£6,556 / week

Ranch at Fox Hollow - Laurel Lake , 4BR's, 4.5 Baths

Lenox house

4 bedrooms / 5 bathrooms / sleeps 11

from £560 / night

£3,761 / week

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

2

from £137 / night

£942 / week

Brook Hill Farm House

Valatie house

4 bedrooms / 3 bathrooms / sleeps 12

from £310 / night

£1,239 / week

Viewing 40 of 139
rentals in West Stockbridge