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> Houses and condos in Southold

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

Price per night

£1 £750 -

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  • 3 and above
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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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2 Holiday homes

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Lakefront
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Great rentals within 20 miles that match your search

Holiday villa in Wingdale

Wingdale villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from £571 / night

£3,377 / 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 £685 / night

£4,563 / 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 home in Middlefield

Middlefield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £457 / night

£2,419 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday home in Middlefield

Middlefield house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £114 / night

£1,141 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Lakefront

4 reviews

from £913 / night

£6,388 / week

1 / 23

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 £264 / night

£2,099 - £2,464 / 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 £391 / night

£2,738 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday home in Little Compton

Little Compton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £391 / night

£2,738 / week

1 / 9

Great rentals within 20 miles that match your search

Bridgehampton holiday home rental

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £391 / night

£2,738 / week

1 / 4

Great rentals within 20 miles that match your search

Wakefield holiday home let

Wakefield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

2 reviews

from £730 / night

£5,111 / week

1 / 20

Great rentals within 20 miles that match your search

Montauk holiday home rental

Montauk house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £1,565 / night

£10,951 / week

1 / 8

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 £822 / night

£5,749 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home with swimming pool in East Hampton

East Hampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £457 / night

£3,194 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home with golf nearby in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £2,008 / night

£11,407 / week

1 / 26

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 £320 / night

£2,236 / week

1 / 11

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 £313 / night

£2,190 / week

1 / 18

Great rentals within 20 miles that match your search

Westerly holiday home rental

Westerly house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Lakefront

from £639 / night

£2,647 - £2,966 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

2 reviews

from £1,095 / night

£7,666 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday private room with shared pool in Southampton

Southampton private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Lakefront

2 reviews

from £283 / night

£1,981 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Narragansett

Narragansett house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Lakefront

2 reviews

from £730 / night

£4,107 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Lakefront

from £848 / night

£5,932 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home rental

Deep River house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £274 / night

£1,917 / week

1 / 57

Great rentals within 20 miles that match your search

Home rental in Southampton

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £522 / night

£3,651 / week

1 / 14

Great rentals within 20 miles that match your search

Southport holiday cottage let

Southport cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Lakefront

from £183 / night

£1,369 / week

1 / 39

Great rentals within 20 miles that match your search

Holiday home with swimming pool in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

from £913 / night

£5,019 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday condo in Montauk

Montauk condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £457 / night

£3,194 / week

1 / 8

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 filter does not match: Lakefront

from £1,369 / night

£9,582 / week

1 / 83

Great rentals within 20 miles that match your search

Home rental in Old Lyme

Old Lyme house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Lakefront

5 reviews

from £261 / night

£1,825 / week

1 / 17

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 £235 / night

£1,643 / 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 £431 / night

£3,012 / week

1 / 6

Great rentals within 20 miles that match your search

Roxbury holiday hotel apartment rental

Roxbury hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

from £228 / night

£1,364 / week

1 / 7

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 £913 / night

£6,388 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Lakefront

from £326 / night

£2,282 / week

1 / 18

Great rentals within 20 miles that match your search

Home rental in Jamestown with golf nearby

Jamestown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Lakefront

from £548 / night

£2,282 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday home in Portsmouth

Portsmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £502 / night

£3,514 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday condo accommodation

Newport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Lakefront

from £388 / night

£2,715 / week

1 / 10

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 £1,369 / night

£7,301 - £9,217 / week

1 / 26

Great rentals within 20 miles that match your search

Mystic holiday home rental

Mystic house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Lakefront

7 reviews

from £822 / night

£5,339 - £6,616 / week

1 / 70

Great rentals within 20 miles that match your search

Holiday cottage rental

Narragansett cottage

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Lakefront

6 reviews

from £343 / night

£2,396 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday cottage in Sag Harbor

Sag Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Lakefront

6 reviews

from £548 / night

£3,450 / week

1 / 15

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