Shelter Island Vacation Rentals | Book Now, Save Up to 30%

All in pricing: Taxes and fees included

Save $542

Preferred host

Entire home in Shelter Island, NY

Nov 16 - 19

$1,285/night

5.0

3

5 bedrooms

8 guests

$4,878$4,336total

Save $88

Whimstay gem

Entire rental unit in Greenport, NY

Nov 16 - 19

$299/night

4.9

56

2 bedrooms

6 guests

$1,095$1,008total

Save $146

Preferred host

Entire home in Greenport, NY

Nov 16 - 19

$499/night

5.0

1

3 bedrooms

6 guests

$1,830$1,684total

Save $1,811

House in Southold, NY

May 8 - 22

$634/night

4.9

11

4 bedrooms

8 guests

Pay only $811 today

$11,841$10,031total

Save $1,611

House in Southold, NY

Nov 16 - 30

$366/night

5.0

4

3 bedrooms

6 guests

$7,395$5,784total

Save $219

Preferred host

Entire home in East Marion, NY

Nov 16 - 30

$160/night

5.0

1

3 bedrooms

6 guests

$2,742$2,522total

Save $201

Preferred host

Entire cottage in Southold, NY

May 14 - 28

$147/night

5.0

1

2 bedrooms

3 guests

Pay only $260 today

$2,512$2,311total

Save $161

House in Peconic, NY

Nov 16 - 19

$502/night

4.8

17

3 bedrooms

7 guests

$1,862$1,701total

Save $490

Preferred host

Entire home in Cutchogue, NY

Feb 28 - Mar 14

$308/night

5.0

3

3 bedrooms

7 guests

Pay only $545 today

$5,331$4,841total

Save $1,357

House in Northwest Harbor, NY

Nov 16 - 30

$489/night

4.0

1

4 bedrooms

8 guests

$9,088$7,731total

Save $249

Guests rave

Entire cottage in Bridgehampton, NY

Nov 21 - 24

$384/night

5.0

30

2 bedrooms

3 guests

$1,549$1,300total

Save $228

Preferred host

Entire cottage in East Hampton, NY

Nov 16 - 21

$467/night

5.0

4

2 bedrooms

4 guests

$2,852$2,623total

Save $426

Guests rave

House in Southampton, NY

Nov 16 - 19

$1,132/night

4.9

86

6 bedrooms

12 guests

$4,264$3,837total

Save $243

House in Mattituck, NY

Nov 16 - 19

$677/night

4.6

13

3 bedrooms

6 guests

$2,536$2,293total

Save $685

Preferred host

Entire home in Mattituck, NY

Nov 16 - 30

$500/night

5.0

2

3 bedrooms

6 guests

$8,558$7,874total

Save $488

House in Water Mill, NY

Dec 1 - 15

$356/night

New

3 bedrooms

6 guests

$6,095$5,608total

Save $732

House in Southampton, NY

Nov 16 - 19

$684/night

4.0

1

4 bedrooms

8 guests

$3,050$2,318total

Save $5,600

Preferred host

House in East Hampton, NY

Jun 18 - Jul 2

$2,909/night

5.0

1

5 bedrooms

10 guests

Pay only $5,157 today

$51,394$45,794total

Save $439

Preferred host

Entire cottage in Amagansett, NY

May 1 - 8

$625/night

4.8

10

4 bedrooms

10 guests

Pay only $554 today

$5,358$4,919total

Save $261

House in Southampton, NY

Nov 16 - 19

$623/night

4.6

54

4 bedrooms

10 guests

$2,370$2,109total

Save $2,235

Entire home in Southampton, NY

Nov 16 - 30

$1,633/night

New

4 bedrooms

10 guests

$27,942$25,707total

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Map shows last minute vacation rentals in Shelter Island