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> Houses and condos in Southold

Houses in Southold and Condos - Holiday Lettings - Holiday Rentals Southold

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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  • Villa (1)
  • House (1)

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Lakefront

Great rentals within 20 miles that match your search

Holiday villa in Wingdale

Wingdale villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £573 / night

£3,389 / week

1 / 29

Great rentals within 20 miles that match your search

Cornwall Bridge holiday home rental

Cornwall Bridge house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7
1 review

from £686 / night

£4,571 / week

1 / 24

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Holiday villa in Southampton

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £818 / night

£5,725 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday home rental

North Kingstown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

from £527 / night

£2,886 - £4,553 / week

1 / 20

Great rentals within 20 miles that match your search

Westhampton Beach holiday home rental

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

4 reviews

from £1,100 / night

£7,695 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Mystic

Mystic house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

1 review

from £261 / night

£1,603 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £916 / night

£3,664 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday home in New London

New London house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Lakefront

1 review

from £265 / night

£2,107 - £2,474 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday condo in Southampton

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £393 / night

£2,748 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday home in Montauk

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £825 / night

£5,771 / week

1 / 19

Great rentals within 20 miles that match your search

Home rental in Greenwich with golf nearby

Greenwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

1 review

from £321 / night

£2,245 / week

1 / 11

Great rentals within 20 miles that match your search

Home rental in Middletown

Middletown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £321 / night

£2,016 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday home in Narragansett

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Lakefront

from £314 / night

£2,199 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday home in Ocean Bay Park

Ocean Bay Park house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Lakefront

1 review

from £2,016 / night

£11,450 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday condo in Newport

Newport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £236 / night

£1,649 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday home in Westport Point

Westport Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £432 / night

£3,023 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Lakefront

from £916 / night

£6,412 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home in Wakefield

Wakefield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £413 / night

£2,840 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday villa in Amagansett

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

from £1,283 / night

£7,695 - £8,977 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday manor house in Amagansett

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £1,100 / night

£7,695 / week

1 / 24

Great rentals within 20 miles that match your search

Home rental in Southampton

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Lakefront

from £2,617 / night

£18,320 / week

1 / 16

Great rentals within 20 miles that match your search

East Hampton holiday home rental

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Lakefront

1 review

from £786 / night

£5,496 / week

1 / 13

Great rentals within 20 miles that match your search

Newport holiday studio rental

Newport studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £107 / night

£748 / week

1 / 22

Great rentals within 20 miles that match your search

Home rental in Baiting Hollow

Baiting Hollow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

1 review

from £641 / night

£4,482 / week

1 / 51

Great rentals within 20 miles that match your search

Montauk holiday manor house rental

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

from £13,740 / night

£96,177 / week

1 / 30

Great rentals within 20 miles that match your search

Home rental in Hampton Bays

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

1 filter does not match: Lakefront

from £975 / night

£6,824 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday farmhouse in East Hampton

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £871 / night

£6,092 / week

1 / 24

Great rentals within 20 miles that match your search

Sag Harbor holiday home rental

Sag Harbor house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

from £779 / night

£5,450 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £1,375 / night

£7,334 - £9,259 / week

1 / 26

Great rentals within 20 miles that match your search

Middletown holiday home rental

Middletown house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 filter does not match: Lakefront

3 reviews

from £321 / night

£2,205 - £2,860 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday home letting

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

4 reviews

from £344 / night

£2,290 / week

1 / 17

Great rentals within 20 miles that match your search

New Haven holiday home rental

New Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

11 reviews

from £164 / night

£1,145 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday villa in Southampton

Southampton villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Lakefront

from £1,832 / night

£10,992 / week

1 / 11

Great rentals within 20 miles that match your search

East Hampton holiday home rental

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

14 reviews

from £786 / night

£5,501 / week

1 / 17

Great rentals within 20 miles that match your search

Stamford holiday apartment rental

Stamford apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Lakefront

3 reviews

from £175 / night

£1,146 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday home in Bridgehampton

Bridgehampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £1,329 / night

£9,297 / week

1 / 13

Great rentals within 20 miles that match your search

Westerly holiday apartment rental

Westerly apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Lakefront

1 review

from £293 / night

£2,046 / week

1 / 32

Great rentals within 20 miles that match your search

Cherry Grove holiday home rental

Cherry Grove house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

1 review

from £481 / night

£3,664 - £4,947 / week

1 / 23

Great rentals within 20 miles that match your search

Little Compton holiday home rental

Little Compton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £413 / night

£2,751 - £5,042 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Jamestown

Jamestown apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Lakefront

7 reviews

from £183 / night

£1,283 / week

1 / 47

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