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Holiday Homes and Apartments Shelter Island, Hamptons and nearby

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 38 Rentals in the Shelter Island Area
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From
$160
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Grill, Washer/Dryer, Internet & more
11 photos Details
Reviews (2) Make Enquiry
From
$801
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 9
Water Views, Other outdoor space, Grill & more
16 photos Details
Reviews (3) Make Enquiry
From
$191
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
Grill, Other outdoor space, Air Conditioning & more
16 photos Details
Make Enquiry
From
$315
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 4
Suitable for children, Air Conditioning & more
7 photos Details
Make Enquiry
From
$381
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
Air Conditioning, Grill, Other outdoor space & more
35 photos Details
Make Enquiry
From
$1,175
Per Night
6 Bedrooms, 8 Bathrooms, Sleeps 12
Suitable for children, Elder access
28 photos Details
Make Enquiry
From
$401
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 6
Elder access, Suitable for children & more
15 photos Details
Make Enquiry

The following rentals are within 10 kilometres of Shelter Island, Long Island, New York.

From
$184
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Elder access, Other outdoor space, Private Beach & more
16 photos Details
Reviews (8) Make Enquiry
From
$534
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Other outdoor space, Air Conditioning, Internet & more
20 photos Details
Reviews (2) Make Enquiry
From
$2,564
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 6
Air Conditioning, Private Beach, Elder access & more
12 photos Details
Reviews (2) Make Enquiry
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From
$187
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Washer/Dryer, Wheelchair access, Elder access & more
13 photos Details
Reviews (1) Make Enquiry
From
$187
Per Night
Studio, Sleeps 3
Private Beach, Parking, Housekeeping Optional & more
23 photos Details
Reviews (9) Make Enquiry
From
$315
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 6
Garden, Grill, Fireplace & more
17 photos Details
Reviews (10) Make Enquiry
From
$394
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Air Conditioning, Heated Pool, Waterfront & more
4 photos Details
Reviews (19) Make Enquiry
From
$330
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Waterfront, Internet & more
4 photos Details
Reviews (23) Make Enquiry
From
$267
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Suitable for children, Air Conditioning & more
11 photos Details
Reviews (1) Make Enquiry
From
$267
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Housekeeping Optional, Fireplace, Air Conditioning & more
23 photos Details
Reviews (2) Make Enquiry
From
$427
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 5
Pet friendly, Suitable for children, Grill & more
11 photos Details
Reviews (1) Make Enquiry
From
$153
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 5
Internet, Grill, Air Conditioning & more
7 photos Details
Make Enquiry
From
$315
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Pet friendly, Internet, Grill & more
11 photos Details
Make Enquiry
From
$183
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Pet friendly, Grill & more
8 photos Details
Make Enquiry
From
$321
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Pet friendly, Washer/Dryer, Private Beach & more
40 photos Details
Make Enquiry
From
$336
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Private pool, Water Views, Canoe & more
10 photos Details
Make Enquiry
From
$214
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 9
Garden, Air Conditioning, Washer/Dryer & more
7 photos Details
Make Enquiry
From
$262
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Water Views, Garden, Internet & more
22 photos Details
Make Enquiry
From
$187
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Parking, Washer/Dryer, Air Conditioning & more
14 photos Details
Make Enquiry
From
$208
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Internet, Private Beach, Smoking allowed & more
12 photos Details
Make Enquiry
From
$533
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Air Conditioning, Waterfront, Wheelchair access & more
8 photos Details
Make Enquiry
From
$321
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children, Elder access
15 photos Details
Make Enquiry
From
$224
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Private Fishing Lake/River, Other outdoor space & more
7 photos Details
Make Enquiry
From
$381
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
Private Pool, Air Conditioning, Hot Tub & more
23 photos Details
Make Enquiry
From
$315
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Other outdoor space, Waterfront, Wheelchair access & more
10 photos Details
Make Enquiry
From
$401
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Suitable for children, Other outdoor space, Internet & more
7 photos Details
Make Enquiry
From
$267
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Grill, Shared Outdoor Pool (Heated), Internet & more
14 photos Details
Make Enquiry
From
$890
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 12
Air Conditioning, Fireplace, Private Pool & more
17 photos Details
Make Enquiry
From
$278
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Suitable for children
8 photos Details
Make Enquiry
From
$347
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
Suitable for children, Elder access
13 photos Details
Make Enquiry
Enquire for rates
2 Bedrooms, 2 Bathrooms, Sleeps 6
Spa/Whirlpool, Air Conditioning, Parking & more
3 photos Details
Make Enquiry
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Book Online(22)
Use filters to find the best results!

Suitability

  • Wheelchair access (4)
  • Elder access (16)
  • Suitable for children (24)
  • Pet friendly (12)
  • Smoking allowed (2)

Amenities

  • Other outdoor space (31)
  • Internet (30)
  • Air Conditioning (29)
  • Grill (26)
  • Fireplace (14)
  • View all amenities
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