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Best Vacation Rentals in Winchester - Holiday Lettings - Cabins

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147 Vacation rentals

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Winchester ski home to rent.

Winchester house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

from $749 / night

$5,243 / week

1 / 30

Winchester ski home to rent.

Winchester house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $407 / night

$2,849 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $259 / night

$1,813 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $465 / night

$3,255 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

from $617 / night

$4,319 / week

1 / 30

Ski home to rent in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $387 / night

$2,709 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $218 / night

$1,526 / week

1 / 30

Home rental in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $314 / night

$2,198 / week

1 / 30

Home rental in Winchester

Winchester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $260 / night

$1,820 / week

1 / 30

Winchester Vacation home rental

Winchester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $260 / night

$1,820 / week

1 / 30

Ski cottage to rent in Winchester

Winchester cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $433 / night

$3,031 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

from $644 / night

$4,508 / week

1 / 30

Winchester ski chalet to rent.

Winchester chalet

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 16

from $620 / night

$4,340 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from $376 / night

$2,632 / week

1 / 30

Ski home to rent in Winchester

Winchester house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $516 / night

$3,612 / week

1 / 30

Ski home to rent in Winchester

Winchester house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 13

from $499 / night

$3,493 / week

1 / 18

Vacation home accommodation

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $329 / night

$2,303 / week

1 / 30

Winchester Vacation home rental

Winchester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 19

from $746 / night

$5,222 / week

1 / 30

Vacation apartment in Winchester

Winchester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $185 / night

$1,295 / week

1 / 15

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $120 / night

$840 / week

1 / 24

Winchester Vacation lodge rental

Winchester lodge

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 18

from $1,133 / night

$7,931 / week

1 / 30

Home rental in Winchester

Winchester house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 8

from $246 / night

$1,722 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $242 / night

$1,694 / week

1 / 30

Ski home to rent in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $310 / night

$2,170 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $203 / night

$1,421 / week

1 / 30

Ski home to rent in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from $346 / night

$2,422 / week

1 / 28

Winchester Vacation home rental

Winchester house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $581 / night

$4,067 / week

1 / 30

Vacation home rental

Winchester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $322 / night

$2,254 / week

1 / 30

Winchester ski home to rent.

Winchester house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 12

from $716 / night

$5,012 / week

1 / 30

Winchester ski home to rent.

Winchester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $254 / night

$1,778 / week

1 / 30

Winchester ski home to rent.

Winchester house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 19

from $1,113 / night

$7,791 / week

1 / 30

Vacation cottage in Winchester

Winchester cottage

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $480 / night

$3,360 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 11

from $668 / night

$4,676 / week

1 / 30

Vacation home rental

Winchester house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 22

from $986 / night

$6,902 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $282 / night

$1,974 / week

1 / 25

Ski home to rent in Winchester

Winchester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $221 / night

$1,547 / week

1 / 22

Winchester ski home to rent.

Winchester house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

from $489 / night

$3,423 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $995 / night

$6,965 / week

1 / 30

Winchester Vacation home rental

Winchester house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

from $509 / night

$3,563 / week

1 / 30

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $447 / night

$3,129 / week

1 / 30