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Family Friendly Holidays in Lenox - Holiday Lettings

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52 family friendly properties

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Holiday apartment in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

“Fun!” My friend and I stayed at Gartner House in late spring, a lovely time to explore the area. So much to see...lots of charming shops and restaurants in Lenox. We walked to breakfast and dinner...also drove to Lee, Stockbridge, and Great Barrington to visit museums, galleries, shops. Gartner House is so comfortable and nicely appointed; it was a great place to call home during our too-short visit. Can't wait to to back!

from £184 / night

£1,100 / week

1 / 21

Holiday home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £230 / night

£1,604 / week

1 / 12

Holiday home in Lenox

Lenox house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 11

from £456 / night

£2,734 / week

1 / 16

Holiday home in Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £318 / night

£2,227 / week

1 / 25

Holiday home with indoor pool in Lenox

Lenox house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from £413 / night

£2,567 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Lee

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £298 / night

£2,086 - £2,727 / week

1 / 12

Holiday log cabin rental

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

from £390 / night

£1,513 - £1,673 / week

1 / 18

Holiday home rental

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

from £239 / night

£1,421 - £2,865 / week

1 / 20

Holiday condo rental

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £344 / night

£2,017 / week

1 / 12

Holiday home in Lee

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £688 / night

£2,750 / week

1 / 7

Great Barrington holiday home rental

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from £138 / night

£871 / week

1 / 14

Holiday home in Hancock

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £2,292 / night

£27,458 / week

1 / 4

Log cabin rental in Hillsdale

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £184 / night

£963 / week

1 / 31

Holiday home in Becket

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £137 / night

£912 / week

1 / 13

Holiday home rental

Valatie house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £223 / night

£1,559 / week

1 / 25

Holiday home in Stockbridge

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £688 / night

£4,125 / week

1 / 22

Holiday home with golf nearby in Lee

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

from £655 / night

£4,583 / week

1 / 18

Monterey holiday home rental

Monterey house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 6

from £505 / night

£3,529 / week

1 / 29

Holiday condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £207 / night

£1,444 / week

1 / 14

Holiday home in Spencertown

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £123 / night

£856 / week

1 / 14

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £138 / night

£825 / week

1 / 4

Holiday farmhouse in Stockbridge

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £138 / night

£825 / week

1 / 4

Williamstown holiday condo rental

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £210 / night

£1,467 / week

1 / 6

Holiday home in Monterey

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £459 / night

£3,208 / week

1 / 23

Holiday home in Hancock

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £138 / night

£867 - £1,989 / week

1 / 26

East Chatham holiday home rental

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £824 / night

£5,768 / week

1 / 42

Holiday tented camp rental

Great Barrington tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £83 / night

£578 - £1,444 / week

1 / 13

Home rental in Becket

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £252 / night

£1,100 / week

1 / 20

Holiday home in Lee

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £321 / night

£2,246 / week

1 / 26

Holiday home rental

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £210 / night

£1,238 - £2,246 / week

1 / 18

Lee holiday apartment rental

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £161 / night

£779 / week

1 / 13

Holiday home in Hinsdale

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £174 / night

£930 - £994 / week

1 / 10

Holiday home in Great Barrington

Great Barrington house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

from £274 / night

£2,415 - £3,181 / week

1 / 30

Holiday tented camp in Richmond

Richmond tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £108 / night

£753 - £938 / week

1 / 12

Stockbridge holiday home rental

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £638 / night

£2,233 - £3,764 / week

1 / 19

Southfield holiday tented camp accommodation

Southfield tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 8

from £110 / night

£868 - £1,302 / week

1 / 12

Hillsdale holiday tented camp rental

Hillsdale tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £92 / night

£721 - £1,015 / week

1 / 19

Holiday tented camp in Tyringham

Tyringham tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £92 / night

£504 - £634 / week

1 / 7

Holiday tented camp in Copake Falls

Copake Falls tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £123 / night

£976 / week

1 / 13

Richmond holiday tented camp rental

Richmond tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £87 / night

£689 - £1,200 / week

1 / 8

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