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Vacation Rentals in Shelter Island, NY

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 23 Rentals in the Shelter Island Area
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From
$750
Per Night
Shelter Island
5 Bedrooms, 4 Bathrooms, Sleeps 9
16 photos Details
Reviews (3) Make Inquiry
From
$150
Per Night
Shelter Island
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Reviews (2) Make Inquiry
From
$1,100
Per Night
Shelter Island
6 Bedrooms, 8 Bathrooms, Sleeps 12
28 photos Details
Make Inquiry

The following rentals are within 5 miles of Shelter Island, Long Island, New York.

From
$250
Per Night
Greenport, NY
4 Bedrooms, 2 Bathrooms, Sleeps 10
15 photos Details
Reviews (2) Make Inquiry
From
$369
Per Night
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Reviews (18) Make Inquiry
From
$309
Per Night
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Reviews (22) Make Inquiry
From
$2,400
Per Week
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (2) Make Inquiry
From
$175
Per Night
Orient, NY
1 Bedroom, 1 Bathroom, Sleeps 3
16 photos Details
Reviews (9) Make Inquiry
From
$295
Per Night
Southold, NY
3 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (8) Make Inquiry
From
$500
Per Night
Southold, NY
4 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (1) Make Inquiry
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From
$200
Per Night
Southold, NY
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Reviews (1) Make Inquiry
From
$1,200
Per Week
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (8) Make Inquiry
From
$185
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
9 photos Details
Reviews (1) Make Inquiry
From
$500
Per Night
East Marion, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Make Inquiry
From
$299
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
17 photos Details
Make Inquiry
From
$550
Per Night
Orient, NY
3 Bedrooms, 2 Bathrooms, Sleeps 5
11 photos Details
Make Inquiry
From
$300
Per Night
Southold, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Make Inquiry
From
$175
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details
Make Inquiry
From
$245
Per Night
Greenport, NY
1 Bedroom, 2 Bathrooms, Sleeps 5
8 photos Details
Make Inquiry
From
$175
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details
Make Inquiry
From
$175
Per Night
Southold, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
12 photos Details
Make Inquiry
From
$375
Per Night
Greenport, NY
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Make Inquiry
Inquire for rates
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
3 photos Details
Make Inquiry
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Book Online(16)

Suitability

  • Wheelchair access (2)
  • Elder access (14)
  • Suitable for children (17)
  • Pet friendly (5)
  • Smoking allowed (2)

Amenities

  • Other outdoor space (18)
  • Air Conditioning (15)
  • Grill (13)
  • Internet (13)
  • Garden or Yard (12)
  • View all amenities
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Book Online(16)

Suitability

  • Wheelchair access (2)
  • Elder access (14)
  • Suitable for children (17)
  • Pet friendly (5)
  • Smoking allowed (2)

Amenities

  • Other outdoor space (18)
  • Air Conditioning (15)
  • Grill (13)
  • Internet (13)
  • Garden or Yard (12)
  • View all amenities