Houses in Shelter Island and Villas – Holiday Lettings - Holiday Rentals Shelter Island

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324 Holiday homes

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

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from £303 / night

£2,117 / week

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Responds fast!
avg. 27 minutes

from £303 / night

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(2) Excellent 

30

Shelter Island holiday home rental

Hamptons / Shelter Island

4 8 14 nights min

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

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from £232 / night

£1,018 - £3,928 / week

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from £232 / night

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26

Shelter Island holiday home let

Hamptons / Shelter Island

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £389 / night

£2,722 / week

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avg. 27 minutes

from £389 / night

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19

Shelter Island holiday home rental

Hamptons / Shelter Island

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Child friendly
  • Air conditioning
  • Private garden

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from £730 / night

£5,106 / week

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from £730 / night

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35

Holiday bungalow in Shelter Island Heights

Shelter Island / Shelter Island Heights

2 6 2 nights min

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

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from £471 / night

£3,294 / week

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Responds fast!
avg. 3 hours 13 minutes

from £471 / night

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49

Holiday villa in Shelter Island Heights

Shelter Island / Shelter Island Heights

6 12 15 nights min

  • 6 bedrooms
  • sleeps 12
  • 15 nights min
  • Ask owner if suitable for children
  • Ask about pets

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from £3,142 / night

£21,994 / week

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avg. 15 minutes

from £3,142 / night

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Great rentals within 20 miles that match your search

Distance approx 16.77 miles from Shelter Island

9

Holiday cottage in Westbrook

Connecticut / Westbrook

2 5 7 nights min

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

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from £274 / night

£1,916 / week

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from £274 / night

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Distance approx 10.08 miles from Shelter Island

(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

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from £449 / night

£3,143 - £3,928 / week

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from £449 / night

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Distance approx 14.23 miles from Shelter Island

(1) Excellent 

28

Southampton holiday home rental

Hamptons / Southampton

5 10 7 nights min

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

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from £2,824 / night

£19,763 / week

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Responds fast!
avg. 1 hour 38 minutes

from £2,824 / night

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Distance approx 10.73 miles from Shelter Island

(1) Very Good 

10

Holiday home in Water Mill

Hamptons / Water Mill

3 6 30 nights min

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

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from £535 / night

£3,928 / week

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from £535 / night

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Distance approx 8.37 miles from Shelter Island

(1) Excellent 

19

Holiday home rental

Hamptons / East Hampton

3 6 min stay varies

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

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from £275 / night

£1,179 - £5,107 / week

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from £275 / night

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Distance approx 2.45 miles from Shelter Island Show on Map

(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

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from £1,905 / night

£13,333 / week

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Responds fast!
avg. 2 hours 46 minutes

from £1,905 / night

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Distance approx 3.94 miles from Shelter Island

(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

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from £589 / night

£5,098 / week

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Responds fast!
avg. 2 hours 41 minutes

from £589 / night

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Distance approx 16.7 miles from Shelter Island

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

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from £180 / night

£1,255 / week

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from £180 / night

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Distance approx 13.94 miles from Shelter Island

4

Southampton holiday hotel apartment rental

Hamptons / Southampton

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

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from £117 / night

£511 / week

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from £117 / night

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Distance approx 4.52 miles from Shelter Island

(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

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from £314 / night

£1,804 / week

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Responds fast!
avg. 2 hours 41 minutes

from £314 / night

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Distance approx 11.39 miles from Shelter Island

38

Holiday villa in Amagansett

Hamptons / Amagansett

5 10 3 nights min

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

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from £943 / night

£6,600 / week

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from £943 / night

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Distance approx 8.76 miles from Shelter Island

24

Home rental in Southampton with shared pool

Hamptons / Southampton

3 6 7 nights min

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

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from £236 / night

£1,647 / week

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from £236 / night

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Distance approx 8.9 miles from Shelter Island

(1) Excellent 

36

Home rental in East Hampton

Hamptons / East Hampton

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

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from £1,121 / night

£7,843 / week

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from £1,121 / night

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Distance approx 8.13 miles from Shelter Island

27

Holiday home in East Hampton

Hamptons / East Hampton

3 6 31 nights min

  • 3 bedrooms
  • sleeps 6
  • 31 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £393 / night

£2,750 / week

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Responds fast!
avg. 3 hours 25 minutes

from £393 / night

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Distance approx 10.77 miles from Shelter Island

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

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from £825 / night

£5,775 / week

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from £825 / night

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Distance approx 13.84 miles from Shelter Island

15

Holiday cottage rental

Hamptons / Southampton

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Add to shortlist

from £1,412 / night

£5,882 / week

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from £1,412 / night

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Distance approx 8.25 miles from Shelter Island

29

East Hampton holiday home rental

Hamptons / East Hampton

3 6 14 nights min

  • 3 bedrooms
  • sleeps 6
  • 14 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

Add to shortlist

from £353 / night

£2,466 / week

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Responds fast!
avg. 30 minutes

from £353 / night

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Distance approx 7.74 miles from Shelter Island

(2) Excellent 

33

Holiday home in Water Mill

Hamptons / Water Mill

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Nearest beach 8 km
  • Swimming pool
  • Child friendly

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from £786 / night

£5,500 / week

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from £786 / night

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Distance approx 9.35 miles from Shelter Island

(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
  • Nearest beach 3 km
  • Child friendly

Add to shortlist

from £393 / night

£1,961 / week

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from £393 / night

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Distance approx 10.18 miles from Shelter Island

11

Holiday home in East Hampton

Hamptons / East Hampton

3 6 2 nights min

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

Add to shortlist

from £702 / night

£3,059 / week

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Responds fast!
avg. 27 minutes

from £702 / night

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Distance approx 7.07 miles from Shelter Island

24

Southampton holiday home rental

Hamptons / Southampton

3 5 6 nights min

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

Add to shortlist

from £313 / night

£2,191 / week

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Responds fast!
avg. 22 minutes

from £313 / night

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Distance approx 15.97 miles from Shelter Island

31

Ski home to rent in Old Saybrook

Connecticut / Old Saybrook

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Ski
  • Child friendly
  • Air conditioning

Add to shortlist

from £295 / night

£2,063 / week

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Responds fast!
avg. 22 minutes

from £295 / night

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Distance approx 13.94 miles from Shelter Island

7

Holiday hotel apartment in Southampton

Hamptons / Southampton

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning

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from £117 / night

£510 / week

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from £117 / night

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Distance approx 4.89 miles from Shelter Island

(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

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from £471 / night

£2,353 / week

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from £471 / night

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Distance approx 7.07 miles from Shelter Island

21

Sagaponack holiday home rental

Hamptons / Sagaponack

5 10 14 nights min

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

Add to shortlist

from £1,345 / night

£9,411 / week

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from £1,345 / night

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Distance approx 17.93 miles from Shelter Island

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

Add to shortlist

from £4,321 / night

£9,428 / week

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from £4,321 / night

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Distance approx 8.37 miles from Shelter Island

(4) Excellent 

18

Home rental in Springs

Hamptons / Springs

4 8 7 nights min

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

Add to shortlist

from £1,059 / night

£7,412 / week

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from £1,059 / night

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Distance approx 10.21 miles from Shelter Island

23

Holiday home in East Hampton

Hamptons / East Hampton

7 12 14 nights min

  • 7 bedrooms
  • sleeps 12
  • 14 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

Add to shortlist

from £2,241 / night

£15,685 / week

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Responds fast!
avg. 3 hours 14 minutes

from £2,241 / night

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Distance approx 7.73 miles from Shelter Island

16

Home rental in Southampton

Hamptons / Southampton

5 12 14 nights min

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

Add to shortlist

from £1,513 / night

£10,588 / week

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from £1,513 / night

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Distance approx 9.31 miles from Shelter Island

12

Holiday home in East Hampton

Hamptons / East Hampton

3 6 30 nights min

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

Add to shortlist

from £654 / night

£4,706 / week

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from £654 / night

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Distance approx 14.45 miles from Shelter Island

(8) Excellent 

6

Holiday home in Amagansett

Hamptons / Amagansett

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly

Add to shortlist

from £471 / night

£3,294 / week

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from £471 / night

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Distance approx 16.31 miles from Shelter Island

10

Holiday home in Hampton Bays

Southampton / Hampton Bays

3 5 2 nights min

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

Add to shortlist

from £294 / night

£1,726 / week

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from £294 / night

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Distance approx 8.23 miles from Shelter Island

7

Southampton holiday home rental

Hamptons / Southampton

4 10 14 nights min

  • 4 bedrooms
  • sleeps 10
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Add to shortlist

from £628 / night

£5,490 / week

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from £628 / night

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Distance approx 3.81 miles from Shelter Island

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

Add to shortlist

from £406 / night

£2,837 / week

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from £406 / night

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