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Houses in Winchelsea and Cottages – Holiday Lettings - Holiday Rentals Winchelsea

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17 Holiday homes

Holiday chalet in Winchelsea Beach

Winchelsea chalet

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £126 / night

£745 - £899 / week

1 / 24

Winchelsea Beach holiday home rental

Winchelsea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £189 / night

£1,323 / week

1 / 15

Holiday caravan/mobile home in Winchelsea

Winchelsea caravan/mobile home

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from £99 / night

£690 / week

1 / 12

Winchelsea holiday home rental

Winchelsea house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £391 / night

£2,734 / week

1 / 18

Holiday caravan/mobile home in Winchelsea

Winchelsea caravan/mobile home

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £102 / night

£714 / week

1 / 14

Holiday home in Winchelsea

Winchelsea house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £540 / night

£3,775 / week

1 / 27

Home rental in Winchelsea

Winchelsea house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £87 / night

£610 / week

1 / 9

Holiday cottage in Winchelsea

Winchelsea cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £248 / night

£935 - £2,429 / week

1 / 39

Cottage rental in Winchelsea

Winchelsea cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £263 / night

£750 - £1,251 / week

1 / 33

Holiday cottage in Winchelsea

Winchelsea cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £247 / night

£705 - £1,063 / week

1 / 27

Winchelsea holiday apartment rental

Winchelsea apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

from £401 / night

£2,170 / week

1 / 14

Bungalow rental in Winchelsea

Winchelsea bungalow

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

from £127 / night

£887 - £1,838 / week

1 / 48

Holiday cottage with golf nearby in Winchelsea

Winchelsea cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £122 / night

£420 - £1,172 / week

1 / 19

Holiday apartment in Winchelsea

Winchelsea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £287 / night

£2,004 / week

1 / 15

Holiday log cabin in Winchelsea

Winchelsea log cabin

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £115 / night

£602 / week

1 / 24

Holiday caravan/mobile home rental

Winchelsea caravan/mobile home

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £98 / night

£367 - £1,017 / week

1 / 27

Winchelsea holiday home rental

Winchelsea house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from £292 / night

£834 - £1,429 / week

1 / 25

Great rentals within 20 miles that match your search

Dymchurch holiday apartment rental

Dymchurch apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £114 / night

£794 / week

1 / 9

Holiday home letting

Pevensey Bay house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £139 / night

£974 - £2,119 / week

1 / 23

Home rental in Rye

Rye house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £195 / night

£916 - £1,603 / week

1 / 15

Cottage rental in Rye

Rye cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £98 / night

£602 / week

1 / 15

Rye holiday cottage rental

Rye cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £98 / night

£602 / week

1 / 6

Holiday b&b rental

Bethersden b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £109 / night

£762 / week

1 / 12

Marden holiday studio rental

Marden studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £81 / night

£561 / week

1 / 19

Holiday b&b in Cranbrook

Cranbrook b&b

  • 3 bedrooms
  • 1 bathroom
  • sleeps 2

from £102 / night

£714 / week

1 / 8

B&b rental in Cranbrook

Cranbrook b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £102 / night

£714 / week

1 / 8

Holiday b&b in Hawkhurst

Hawkhurst b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

from £81 / night

£561 / week

1 / 8

Dymchurch holiday apartment rental

Dymchurch apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £82 / night

£569 - £973 / week

1 / 14

Holiday b&b rental

Chilham b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £178 / night

£1,243 / week

1 / 4

Rye holiday apartment rental

Rye apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £138 / night

£630 / week

1 / 13

Holiday b&b accommodation

Bethersden b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £109 / night

£762 / week

1 / 8

Holiday tented camp in Wadhurst

Wadhurst tented camp

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £114 / night

£794 / week

1 / 8

Holiday apartment in Hastings

Hastings apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £107 / night

£745 - £859 / week

1 / 76

Home rental in Peasmarsh

Peasmarsh house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £224 / night

£1,563 / week

1 / 15

Camber holiday chalet rental

Camber chalet

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £115 / night

£802 / week

1 / 10

Holiday b&b in Robertsbridge

Robertsbridge b&b

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 6

from £275 / night

£1,443 / week

1 / 12

Holiday home with golf nearby in Hythe

Hythe house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £92 / night

£516 - £916 / week

1 / 23

Holiday apartment rental

Sovereign Harbour South apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £126 / night

£802 - £974 / week

1 / 27

Holiday townhouse in Sovereign Harbour South

Sovereign Harbour South townhouse

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £201 / night

£1,317 - £1,483 / week

1 / 19

Holiday cottage with shared pool in East Hill, Sussex

East Hill, Sussex cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £139 / night

£771 - £1,769 / week

1 / 57

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Top Destination reviews

Winchelsea Beach - Beautiful Beach House
Amazing beach house!

We have just arrived home from the most fantastic short break in this magical beach house! I honestly fell in love with this beautiful property. It was such a delight to stay in a rental that you could tell was so very loved and well looked after by its owners. The interior was immaculate, and the owners were so helpful, answering any questions/queries straight away. We miss it already and will definitely be back! see more
Winchelsea Beach Holiday Annex with river frontage
Very relaxing location

One of the best holiday self catering we have stayed in. Very well equipped kitchen, comfortable lounge, and bedroom. Outside space with amazing views with tranquil River where we relaxed and fished. Special thanks to Connie and clem. … see more

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