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

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

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

from £303 / night

£2,117 / week

Book View

Responds fast!
avg. 27 minutes

from £303 / night

(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

from £232 / night

£1,018 - £3,928 / week

Book View

from £232 / night

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

from £389 / night

£2,722 / week

Book View

Responds fast!
avg. 27 minutes

from £389 / night

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

from £730 / night

£5,106 / week

Book View

from £730 / night

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

from £471 / night

£3,294 / week

Book View

Responds fast!
avg. 3 hours 13 minutes

from £471 / night

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

from £3,142 / night

£21,994 / week

Book View

Responds fast!
avg. 15 minutes

from £3,142 / night

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

from £274 / night

£1,916 / week

Book View

from £274 / night

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

from £449 / night

£3,143 - £3,928 / week

Book View

from £449 / night

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

from £2,824 / night

£19,763 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from £2,824 / night

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

from £535 / night

£3,928 / week

Book View

from £535 / night

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

from £275 / night

£1,179 - £5,107 / week

Book View

from £275 / night

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

from £1,905 / night

£13,333 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £1,905 / night

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

from £589 / night

£5,098 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £589 / night

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

from £180 / night

£1,255 / week

Book View

from £180 / night

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

from £117 / night

£511 / week

Book View

from £117 / night

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

from £314 / night

£1,804 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from £314 / night

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

from £943 / night

£6,600 / week

Book View

from £943 / night

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

from £236 / night

£1,647 / week

Book View

from £236 / night

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

from £1,121 / night

£7,843 / week

Book View

from £1,121 / night

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

from £393 / night

£2,750 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £393 / night

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

from £825 / night

£5,775 / week

Book View

from £825 / night

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

from £1,412 / night

£5,882 / week

Book View

from £1,412 / night

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

from £353 / night

£2,466 / week

Book View

Responds fast!
avg. 30 minutes

from £353 / night

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

from £786 / night

£5,500 / week

Book View

from £786 / night

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

from £393 / night

£1,961 / week

Book View

from £393 / night

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

from £702 / night

£3,059 / week

Book View

Responds fast!
avg. 27 minutes

from £702 / night

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

from £313 / night

£2,191 / week

Book View

Responds fast!
avg. 22 minutes

from £313 / night

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

from £295 / night

£2,063 / week

Book View

Responds fast!
avg. 22 minutes

from £295 / night

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

from £117 / night

£510 / week

Book View

from £117 / night

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

from £471 / night

£2,353 / week

Book View

from £471 / night

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

from £1,345 / night

£9,411 / week

Book View

from £1,345 / night

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

from £4,321 / night

£9,428 / week

Book View

from £4,321 / night

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

from £1,059 / night

£7,412 / week

Book View

from £1,059 / night

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

from £2,241 / night

£15,685 / week

Book View

Responds fast!
avg. 3 hours 14 minutes

from £2,241 / night

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

from £1,513 / night

£10,588 / week

Book View

from £1,513 / night

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

from £654 / night

£4,706 / week

Book View

from £654 / night

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

from £471 / night

£3,294 / week

Book View

from £471 / night

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

from £294 / night

£1,726 / week

Book View

from £294 / night

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

from £628 / night

£5,490 / week

Book View

from £628 / night

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

from £406 / night

£2,837 / week

Book View

from £406 / night

Also consider