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Best Vacation Rentals in Winchester - Holiday Lettings - Cabins

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28 Vacation rentals

Vacation cottage rental

Pitt cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $190 / night

$1,094 - $2,019 / week

1 / 31

Vacation log cabin rental

Winchester log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $180 / night

$1,072 - $3,099 / week

1 / 20

Vacation apartment in Winchester

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $197 / night

$1,240 - $1,459 / week

1 / 8

Studio rental in Winchester with golf nearby

Winchester studio

  • Studio
  • 2 bathrooms
  • sleeps 7

from $263 / night

$1,677 - $1,969 / week

1 / 15

Vacation cottage in Winchester

Winchester cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $219 / night

$1,306 / week

1 / 18

Vacation apartment rental

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $193 / night

$1,167 / week

1 / 20

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from $219 / night

$1,532 / week

1 / 19

Home rental in Winchester

Winchester house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $490 / night

$2,646 - $4,094 / week

1 / 22

Winchester Vacation apartment rental

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $254 / night

$1,791 / week

1 / 10

Vacation apartment in Winchester

Winchester apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $270 / night

$1,889 / week

1 / 12

Apartment rental in Winchester

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $175 / night

$1,225 / week

1 / 12

Vacation home in Winchester

Winchester house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from $391 / night

$2,739 / week

1 / 11

Vacation home in Winchester

Winchester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $452 / night

$3,163 - $4,333 / week

1 / 33

Winchester Vacation b&b rental

Winchester b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $139 / night

$970 / week

1 / 27

Vacation log cabin with golf nearby in Winchester

Winchester log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $164 / night

$1,145 / week

1 / 14

Vacation apartment with golf nearby in Winchester

Winchester apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $154 / night

$868 - $1,072 / week

1 / 22

Vacation log cabin rental

Winchester log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $226 / night

$963 - $2,808 / week

1 / 13

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from $576 / night

$2,819 / week

1 / 53

Vacation guest house in Winchester

Winchester guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $146 / night

$934 - $1,313 / week

1 / 22

Vacation home rental

Winchester house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $219 / night

$1,532 / week

1 / 15

Vacation lodge with golf nearby in Winchester

Winchester lodge

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $209 / night

$1,247 - $3,486 / week

1 / 20

Vacation log cabin with golf nearby in Winchester

Winchester log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $181 / night

$1,262 / week

1 / 12

Home rental in Winchester

Winchester house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $256 / night

$1,677 - $2,188 / week

1 / 17

Vacation home rental

Winchester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $285 / night

$1,991 / week

1 / 15

Vacation lodge with golf nearby in Winchester

Winchester lodge

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $180 / night

$1,072 - $3,099 / week

1 / 21

Vacation cottage rental

Winchester cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $212 / night

$1,386 - $1,998 / week

1 / 19

Vacation home in Winchester

Winchester house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $285 / night

$1,991 / week

1 / 21

Vacation cottage in Winchester

Winchester cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $183 / night

$1,160 - $1,787 / week

1 / 34

Great rentals within 20 miles that match your search

Vacation apartment in Longparish

Longparish apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $130 / night

$909 / week

1 / 31

Vacation apartment in Southampton

Southampton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $189 / night

$1,014 - $1,524 / week

1 / 14

Vacation lodge in Winterslow

Winterslow lodge

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $130 / night

$909 / week

1 / 12

Whiteparish Vacation home rental

Whiteparish house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $237 / night

$766 - $2,695 / week

1 / 11

Vacation home rental

East Boldre house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $156 / night

$493 - $1,400 / week

1 / 8

Vacation apartment in Lee-on-the-Solent

Lee-on-the-Solent apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $183 / night

$875 / week

1 / 21

Vacation chalet in East Meon

East Meon chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $40 / night

$281 / week

1 / 32

Bungalow rental in Bursledon

Bursledon bungalow

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

from $167 / night

$1,167 / week

1 / 32

Vacation cottage in Alresford

Alresford cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $256 / night

$1,532 / week

1 / 25

Vacation cottage in Brockenhurst

Brockenhurst cottage

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from $1,896 / night

$1,823 - $4,229 / week

1 / 20

Cottage rental in Liss

Liss cottage

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $154 / night

$1,021 - $1,167 / week

1 / 57

Vacation home in Beaulieu

Beaulieu house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from $948 / night

$6,636 / week

1 / 9