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

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284 Holiday homes

(2) Excellent 

17

Holiday home letting

North Fork / Southold

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Child friendly

from £287 / night

£1,914 / week

Book View

from £287 / night

34

Holiday home with golf nearby in Southold

North Fork / Southold

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 1 km
  • Child friendly
  • Air conditioning

from £267 / night

£1,530 / week

Book View

from £267 / night

(1) Excellent 

19

Southold holiday home rental

North Fork / Southold

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 0.8 km
  • Swimming pool
  • Child friendly

from £230 / night

£1,608 / week

Book View

from £230 / night

5

Southold holiday cottage rental

North Fork / Southold

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £230 / night

£1,531 / week

Book View

from £230 / night

15

Holiday home in Southold

North Fork / Southold

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £356 / night

£2,488 / week

Book View

from £356 / night

18

Home rental in Southold

North Fork / Southold

5 10 14 nights min

  • 5 bedrooms
  • sleeps 10
  • 14 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £383 / night

£2,679 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £383 / night

19

Home rental in Southold

North Fork / Southold

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £287 / night

£2,009 / week

Book View

from £287 / night

Great rentals within 20 miles that match your search

Distance approx 5.66 miles from Southold

(2) Excellent 

30

Shelter Island holiday home rental

Hamptons / Shelter Island

4 8 15 nights min

  • 4 bedrooms
  • sleeps 8
  • 15 nights min
  • Nearest beach 1 km
  • Child friendly
  • Air conditioning

from £227 / night

£993 / week

Book View

from £227 / night

Distance approx 17.59 miles from Southold

15

Holiday home rental

Hamptons / East Quogue

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £729 / night

£5,100 / week

Book View

Responds fast!
avg. 3 hours 23 minutes

from £729 / night

Distance approx 15.2 miles from Southold

10

Holiday cottage in Westbrook

Connecticut / Westbrook

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £176 / night

£1,227 / week

Book View

from £176 / night

Distance approx 17.88 miles from Southold

11

Holiday cottage rental

Hamptons / Amagansett

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £192 / night

£1,339 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £192 / night

Distance approx 9.87 miles from Southold

22

Holiday villa in Southampton

Hamptons / Southampton

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £685 / night

£4,793 / week

Book View

from £685 / night

Distance approx 11.56 miles from Southold

28

Water Mill holiday home rental

Hamptons / Water Mill

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £767 / night

£5,368 / week

Book View

from £767 / night

Distance approx 4.6 miles from Southold

(5) Excellent 

44

Greenport holiday home accommodation

North Fork / Greenport

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

from £576 / night

£4,985 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £576 / night

Distance approx 15.24 miles from Southold

(5) Excellent 

41

East Hampton holiday home rental

Hamptons / East Hampton

5 12 1 night min

  • 5 bedrooms
  • sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £460 / night

£3,221 / week

Book View

Responds fast!
avg. 3 hours 55 minutes

from £460 / night

Distance approx 3.12 miles from Southold Show on Map

24

Holiday cottage with swimming pool in Shelter Island Heights

Shelter Island / Shelter Island Heights

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £296 / night

£2,067 / week

Book View

Responds fast!
avg. 24 minutes

from £296 / night

Distance approx 16.04 miles from Southold

15

Holiday home with golf nearby in East Hampton

Hamptons / East Hampton

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden

from £493 / night

£3,451 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from £493 / night

Distance approx 15.27 miles from Southold

(1) Excellent 

6

East Hampton holiday home rental

Hamptons / East Hampton

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Nearest beach 4 km
  • Swimming pool
  • Air conditioning

from £439 / night

£3,068 - £3,834 / week

Book View

from £439 / night

Distance approx 12.77 miles from Southold

86

Home rental in East Hampton

Hamptons / East Hampton

7 22 3 nights min

  • 7 bedrooms
  • sleeps 22
  • 3 nights min
  • Child friendly

from £1,562 / night

£10,930 / week

Book View

from £1,562 / night

Distance approx 8.55 miles from Southold

(1) Excellent 

11

Holiday home in Sag Harbor

Hamptons / Sag Harbor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets

from £460 / night

£2,301 / week

Book View

from £460 / night

Distance approx 16.72 miles from Southold

11

East Hampton holiday home rental

Hamptons / East Hampton

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £765 / night

£5,354 / week

Book View

from £765 / night

Distance approx 12.02 miles from Southold

6

Holiday hotel apartment in Southampton

Hamptons / Southampton

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning

from £115 / night

£499 / week

Book View

from £115 / night

Distance approx 13.9 miles from Southold

11

Home rental in East Hampton with swimming pool

Hamptons / East Hampton

5 12 3 nights min

  • 5 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £576 / night

£4,026 / week

Book View

from £576 / night

Distance approx 11.62 miles from Southold

10

Holiday home in East Hampton

Hamptons / East Hampton

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly

from £576 / night

£2,914 / week

Book View

from £576 / night

Distance approx 14.61 miles from Southold

17

Holiday home in East Hampton

Hamptons / East Hampton

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £421 / night

£2,945 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £421 / night

Distance approx 10.22 miles from Southold

16

Holiday home in East Hampton

Hamptons / East Hampton

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1,071 / night

£7,496 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from £1,071 / night

Distance approx 13.66 miles from Southold

22

Holiday home rental

Hamptons / Westhampton Beach

4 6 14 nights min

  • 4 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £767 / night

£5,368 / week

Book View

from £767 / night

Distance approx 12.02 miles from Southold

9

Holiday hotel apartment rental

Hamptons / Southampton

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Air conditioning

from £115 / night

£499 / week

Book View

from £115 / night

Distance approx 12.21 miles from Southold

7

Home rental in Southampton

Hamptons / Southampton

5 16 7 nights min

  • 5 bedrooms
  • sleeps 16
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

from £984 / night

£6,884 / week

Book View

from £984 / night

Distance approx 12.07 miles from Southold

7

Home rental in East Hampton

Hamptons / East Hampton

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Air conditioning
  • Ask about pets

from £306 / night

£2,142 / week

Book View

Responds fast!
avg. 3 hours 49 minutes

from £306 / night

Distance approx 12.76 miles from Southold

25

Holiday home rental

Southampton / Hampton Bays

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from £383 / night

£2,677 / week

Book View

from £383 / night

Distance approx 11.8 miles from Southold

13

Home rental in East Hampton

Hamptons / East Hampton

4 8 90 nights min

  • 4 bedrooms
  • sleeps 8
  • 90 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

from £90 / night

£625 / week

Book View

from £90 / night

Distance approx 4.63 miles from Southold

16

Holiday farmhouse in Greenport

North Fork / Greenport

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £397 / night

£2,774 / week

Book View

from £397 / night

Distance approx 11.99 miles from Southold

5

Southampton holiday home rental

Hamptons / Southampton

2 6 14 nights min

  • 2 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from £658 / night

£4,601 / week

Book View

from £658 / night

Distance approx 4.26 miles from Southold Show on Map

13

Holiday home in Greenport

North Fork / Greenport

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £354 / night

£2,475 / week

Book View

from £354 / night

Distance approx 7.85 miles from Southold

25

Holiday home in Mattituck

North Fork / Mattituck

4 14 30 nights min

  • 4 bedrooms
  • sleeps 14
  • 30 nights min
  • Child friendly
  • Pet friendly

from £1,151 / night

£8,052 / week

Book View

from £1,151 / night

Distance approx 12.02 miles from Southold

9

Hotel apartment rental in Southampton

Hamptons / Southampton

1 1 1 night min

  • 1 bedroom
  • sleeps 1
  • 1 night min
  • Child friendly
  • Air conditioning

from £159 / night

£1,114 / week

Book View

from £159 / night

Distance approx 8.19 miles from Southold

17

Holiday home in Southampton

Hamptons / Southampton

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Child friendly

from £361 / night

£2,524 / week

Book View

from £361 / night

Distance approx 14.07 miles from Southold

22

Holiday home in East Hampton

Hamptons / East Hampton

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden

from £432 / night

£2,761 / week

Enquire View

from £432 / night

Distance approx 13.25 miles from Southold

8

East Hampton holiday home let

Hamptons / East Hampton

5 8 min stay varies

  • 5 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly

from £498 / night

£3,060 - £7,649 / week

Book View

from £498 / night