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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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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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  • Apartment (2)
  • House (2)

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4 Holiday homes

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Great rentals within 20 miles that match your search

Holiday apartment in Misquamicut

Misquamicut apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £550 / night

£2,474 / week

1 / 8

Great rentals within 20 miles that match your search

Apartment rental in Misquamicut

Misquamicut apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £550 / night

£2,107 - £2,748 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday home rental

Misquamicut house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £458 / night

£2,565 / week

1 / 13

Great rentals within 20 miles that match your search

Westerly holiday home rental

Westerly house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £642 / night

£2,657 - £2,977 / week

1 / 17

Great rentals within 20 miles that match your search

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Holiday villa in Southampton

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Smokers

from £818 / night

£5,725 / week

1 / 22

Great rentals within 20 miles that match your search

Holiday home in Stonington

Stonington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Smokers

from £182 / night

£1,237 / week

1 / 25

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: Smokers

4 reviews

from £1,100 / night

£7,695 / week

1 / 45

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: Smokers

from £916 / night

£3,664 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday home rental

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Smokers

7 reviews

from £916 / night

£6,412 / week

1 / 20

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: Smokers

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: Smokers

from £393 / night

£2,748 / week

1 / 21

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: Smokers

from £393 / night

£2,748 / week

1 / 4

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: Smokers

from £1,571 / night

£10,992 / 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: Smokers

from £825 / night

£5,771 / 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: Smokers

from £458 / night

£3,206 / 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: Smokers

from £2,016 / night

£11,450 / week

1 / 26

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: Smokers

2 reviews

from £284 / night

£1,988 / week

1 / 14

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: Smokers

from £851 / night

£5,954 / week

1 / 20

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: Smokers

from £524 / night

£3,664 / week

1 / 14

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: Smokers

from £916 / night

£5,038 / 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: Smokers

from £458 / night

£3,206 / 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: Smokers

from £1,374 / night

£9,618 / week

1 / 83

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: Smokers

from £916 / night

£6,412 / 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: Smokers

from £327 / night

£2,290 / week

1 / 18

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: Smokers

from £1,283 / night

£7,695 - £8,977 / week

1 / 38

Great rentals within 20 miles that match your search

Holiday townhouse in Southampton

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

1 filter does not match: Smokers

from £118 / night

£823 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

1 filter does not match: Smokers

from £1,636 / night

£11,450 / week

1 / 18

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: Smokers

from £1,100 / night

£7,695 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday cottage rental

Southampton cottage

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 10

1 filter does not match: Smokers

from £2,617 / night

£18,320 / week

1 / 15

Great rentals within 20 miles that match your search

Amagansett holiday home rental

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Smokers

from £1,047 / night

£7,328 / week

1 / 11

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: Smokers

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: Smokers

1 review

from £786 / night

£5,496 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

1 filter does not match: Smokers

from £9,814 / night

£68,698 / week

1 / 38

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: Smokers

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: Smokers

from £13,740 / night

£96,177 / week

1 / 30

Great rentals within 20 miles that match your search

Home accommodation in Orient

Orient house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Smokers

from £871 / night

£6,092 / week

1 / 31

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: Smokers

from £871 / night

£6,092 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Smokers

3 reviews

from £732 / night

£3,847 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday private room rental

Springs private room

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

1 filter does not match: Smokers

from £275 / night

£1,924 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Smokers

from £306 / night

£2,138 / week

1 / 16

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