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

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323 Holiday homes

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 £239 / night

£1,593 / week

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from £239 / 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 £370 / night

£2,588 / week

Book View

from £370 / night

(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 £299 / night

£1,991 / week

Book View

from £299 / 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 £239 / night

£1,672 / week

Book View

from £239 / 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 £278 / night

£1,592 / week

Book View

from £278 / 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 £393 / night

£2,750 / week

Book View

Responds fast!
avg. 1 hour 49 minutes

from £393 / night

24

Holiday home in Southold

North Fork / Southold

3 6 14 nights min

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

from £279 / night

£1,951 / week

Book View

Responds fast!
avg. 10 minutes

from £279 / 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 £299 / night

£2,090 / week

Book View

from £299 / night

Great rentals within 20 miles that match your search

Distance approx 4.38 miles from Southold Show on Map

(9) Excellent 

18

Holiday cottage in Cutchogue

North Fork / Cutchogue

2 6 14 nights min

  • 2 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly

from £118 / night

£766 - £1,674 / week

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from £118 / night

Distance approx 12.73 miles from Southold

28

Holiday home in Southampton

Hamptons / Southampton

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

from £667 / night

£4,669 / week

Book View

Responds fast!
avg. 9 minutes

from £667 / night

Distance approx 14.89 miles from Southold

14

Hampton Bays holiday home rental

Southampton / Hampton Bays

6 12 14 nights min

  • 6 bedrooms
  • sleeps 12
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £786 / night

£5,499 / week

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from £786 / night

Distance approx 6.21 miles from Southold

(4) Excellent 

23

East Marion holiday cottage rental

North Fork / East Marion

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden

from £315 / night

£1,807 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £315 / night

Distance approx 11.01 miles from Southold

(2) Very Good 

9

Holiday apartment in Jamesport

North Fork / Jamesport

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 2 km
  • Car not necessary
  • Air conditioning

from £157 / night

£1,095 / week

Book View

from £157 / night

Distance approx 9.41 miles from Southold

13

Holiday apartment in Mattituck

North Fork / Mattituck

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Ask owner if suitable for children

from £703 / night

£2,750 - £7,149 / week

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from £703 / night

Distance approx 6.06 miles from Southold

(5) Excellent 

28

Sag Harbor holiday home rental

Hamptons / Sag Harbor

5 12 7 nights min

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

from £1,908 / night

£13,355 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £1,908 / night

Distance approx 15.2 miles from Southold

23

Holiday home in Hampton Bays

Southampton / Hampton Bays

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £511 / night

£3,575 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £511 / night

Distance approx 15.24 miles from Southold

17

Holiday cottage with shared pool in East Hampton

Hamptons / East Hampton

1 4 1 night min

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

from £119 / night

£830 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from £119 / 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 £786 / night

£5,499 / week

Book View

from £786 / night

Distance approx 11.98 miles from Southold

(14) Excellent 

24

East Hampton holiday home rental

Hamptons / East Hampton

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool

from £283 / night

£1,975 - £3,951 / week

Book View

Responds fast!
avg. 2 hours 53 minutes

from £283 / 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 £197 / night

£1,375 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £197 / night

Distance approx 13.99 miles from Southold

(5) Excellent 

13

Holiday home in East Hampton

Hamptons / East Hampton

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool

from £1,139 / night

£7,659 / week

Book View

from £1,139 / night

Distance approx 5.19 miles from Southold

21

Holiday cottage in New Suffolk

North Fork / New Suffolk

4 8 14 nights min

  • 4 bedrooms
  • sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £292 / night

£2,043 / week

Book View

from £292 / night

Distance approx 6.34 miles from Southold

13

Holiday home in Sag Harbor

Hamptons / Sag Harbor

2 6 7 nights min

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

from £505 / night

£3,535 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £505 / night

Distance approx 15.9 miles from Southold

24

Holiday manor house in Amagansett

Hamptons / Amagansett

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £825 / night

£5,774 / week

Book View

from £825 / night

Distance approx 9.66 miles from Southold

24

Water Mill holiday home rental

Hamptons / Water Mill

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 6 km
  • Swimming pool
  • Child friendly

from £531 / night

£3,712 / week

Book View

from £531 / night

Distance approx 12.64 miles from Southold

(2) Excellent 

12

Holiday home in East Hampton

Hamptons / East Hampton

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

from £780 / night

£5,460 / week

Book View

from £780 / night

Distance approx 12.91 miles from Southold

27

Holiday home in East Hampton

Hamptons / East Hampton

3 6 min stay varies

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

from £354 / night

£4,674 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £354 / night

Distance approx 15.45 miles from Southold

11

Holiday villa in Southampton

Hamptons / Southampton

6 12 14 nights min

  • 6 bedrooms
  • sleeps 12
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £4,321 / night

£9,427 / week

Book View

from £4,321 / night

Distance approx 9.4 miles from Southold

4

Bridgehampton holiday home rental

Hamptons / Bridgehampton

2 4 90 nights min

  • 2 bedrooms
  • sleeps 4
  • 90 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £339 / night

£2,370 / week

Book View

from £339 / night

Distance approx 15.01 miles from Southold

24

Holiday farmhouse in East Hampton

Hamptons / East Hampton

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £511 / night

£3,575 / week

Book View

from £511 / night

Distance approx 10.87 miles from Southold

20

East Hampton holiday home rental

Hamptons / East Hampton

6 11 7 nights min

  • 6 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £903 / night

£6,321 / week

Book View

from £903 / night

Distance approx 12.17 miles from Southold

17

Holiday home in Southampton

Hamptons / Southampton

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1,179 / night

£8,249 / week

Book View

from £1,179 / night

Distance approx 14.01 miles from Southold

(2) Excellent 

19

Home rental in East Hampton

Hamptons / East Hampton

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Child friendly

from £1,764 / night

£11,744 / week

Book View

from £1,764 / night

Distance approx 12.19 miles from Southold

101

Holiday home with swimming pool in Southampton

Hamptons / Southampton

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

from £864 / night

£5,499 - £6,599 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £864 / night

Distance approx 16.01 miles from Southold

9

Holiday home in East Hampton

Hamptons / East Hampton

3 5 30 nights min

  • 3 bedrooms
  • sleeps 5
  • 30 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £338 / night

£2,365 / week

Book View

from £338 / night

Distance approx 12.3 miles from Southold

24

Holiday home in East Hampton

Hamptons / East Hampton

5 10 7 nights min

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

from £1,571 / night

£10,998 - £11,548 / week

Book View

from £1,571 / night

Distance approx 19.26 miles from Southold

11

Amagansett holiday home rental

Hamptons / Amagansett

3 5 30 nights min

  • 3 bedrooms
  • sleeps 5
  • 30 nights min
  • Child friendly
  • Pet friendly

from £1,048 / night

£7,331 / week

Book View

from £1,048 / night

Distance approx 8.69 miles from Southold

8

Holiday home in East Hampton

Hamptons / East Hampton

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Child friendly

from £505 / night

£3,535 / week

Book View

from £505 / night

Distance approx 14 miles from Southold

12

Home letting in Southampton

Hamptons / Southampton

4 8 30 nights min

  • 4 bedrooms
  • sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £446 / night

£3,116 / week

Book View

from £446 / night

Distance approx 11.79 miles from Southold

21

Holiday condo in Southampton

Hamptons / Southampton

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Child friendly
  • Air conditioning

from £339 / night

£2,370 / week

Book View

from £339 / night

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