Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Best Pittsfield Apartments on Holiday Lettings - Apartment rentals

All filters

Filters

48 Vacation rentals

Vacation home in Pittsfield

Pittsfield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $312 / night

$2,184 / week

1 / 22

Pittsfield ski home to rent.

Pittsfield house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from $488 / night

$3,416 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $278 / night

$1,946 / week

1 / 27

Ski home to rent in Pittsfield

Pittsfield house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from $550 / night

$3,850 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 8 bedrooms
  • 3 bathrooms
  • sleeps 25

from $395 / night

$2,765 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

from $1,700 / night

$11,900 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $557 / night

$3,899 / week

1 / 30

Pittsfield ski home to rent.

Pittsfield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $262 / night

$1,834 / week

1 / 21

Ski home to rent in Pittsfield

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $430 / night

$3,010 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $593 / night

$4,151 / week

1 / 25

Pittsfield ski home to rent.

Pittsfield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $290 / night

$2,030 / week

1 / 26

Ski cottage to rent in Pittsfield

Pittsfield cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $225 / night

$1,575 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

from $500 / night

$3,500 / week

1 / 30

Pittsfield ski home to rent.

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $267 / night

$1,869 / week

1 / 30

Home rental in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $135 / night

$945 / week

1 / 15

Pittsfield ski home to rent.

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $406 / night

$2,842 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $270 / night

$1,890 / week

1 / 30

Vacation home in Pittsfield

Pittsfield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $299 / night

$2,093 / week

1 / 30

Vacation home in Pittsfield

Pittsfield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $450 / night

$3,150 / week

1 / 30

Pittsfield Vacation home rental

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $230 / night

$1,610 / week

1 / 13

Vacation home in Pittsfield

Pittsfield house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from $500 / night

$3,500 / week

1 / 26

Vacation home in Pittsfield

Pittsfield house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $193 / night

$1,351 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $410 / night

$2,870 / week

1 / 30

Pittsfield Vacation home rental

Pittsfield house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $162 / night

$1,134 / week

1 / 25

Vacation apartment in Pittsfield

Pittsfield apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $75 / night

$525 / week

1 / 22

Vacation home in Pittsfield

Pittsfield house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $481 / night

$3,367 / week

1 / 30

Home rental in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $184 / night

$1,288 / week

1 / 30

Vacation home in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $125 / night

$875 / week

1 / 20

Pittsfield Vacation home rental

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

from $261 / night

$1,827 / week

1 / 30

Ski apartment to rent in Pittsfield

Pittsfield apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $299 / night

$2,093 / week

1 / 30

Ski home to rent in Pittsfield

Pittsfield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $173 / night

$1,211 / week

1 / 8

Vacation home in Pittsfield

Pittsfield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $366 / night

$2,562 / week

1 / 30

Pittsfield ski home to rent.

Pittsfield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $425 / night

$2,975 / week

1 / 30

Pittsfield Vacation home rental

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Pricing unknown

1 / 24

Home rental in Pittsfield

Pittsfield house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 8

from $238 / night

$1,666 / week

1 / 13

Condo accommodation in Pittsfield

Pittsfield condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $654 / night

$4,578 / week

1 / 28

Vacation home in Pittsfield

Pittsfield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $450 / night

$3,150 / week

1 / 20

Vacation condo rental

Pittsfield condo

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $364 / night

$2,548 / week

1 / 30

Vacation apartment rental

Pittsfield apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $199 / night

$1,393 / week

1 / 6

Vacation apartment in Pittsfield

Pittsfield apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $150 / night

$1,050 / week

1 / 11