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Holiday Homes in Shelter Island

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46 rentals in Shelter Island.
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Newly renovated! Quiet, private, short walk to the beach.
3 bedrooms
3 bathrooms
Sleeps 6
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Charming A-Frame Home On Private Quiet Road
3 bedrooms
1 bathroom
Sleeps 6
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Beautiful, Waterfront Home With Dock And Heated Gunite Pool!
4 bedrooms
3 bathrooms
Sleeps 10
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Charming, Renovated Island Cottage - Shelter Island License #: ********
2 bedrooms
1 bathroom
Sleeps 4
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Relaxing Getaway in the Heart of Shelter Island - great for families and couples
3 bedrooms
1 bathroom
Sleeps 6
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Perfect Family Summer Vacation Home Close to beach 18x42 pool
3 bedrooms
3 bathrooms
Sleeps 6
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Farmhouse Nestled by Meadow, Pool, Near Beaches and Centrally Located!
4 bedrooms
3 bathrooms
Sleeps 8
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Secluded Family Home on Shelter Island.
4 bedrooms
3 bathrooms
Sleeps 8
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New Listing: High-End 8-Acre, 2-Home Estate on Shelter Island w/ Manicured...
6 bedrooms
7 bathrooms
Sleeps 10
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Private Hamptons Cottage
5 bedrooms
2 bathrooms
Sleeps 10
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Waterfront Estate on Shelter Island. 200 Ft on Water. 100 Ft Dock.
4 bedrooms
3 bathrooms
Sleeps 8
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3 other travellers have booked this property
Shelter Island Escape Awaits
4 bedrooms
3 bathrooms
Sleeps 8
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Shelter Island Waterfront Home!
5 bedrooms
4 bathrooms
Sleeps 10
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Charming Shelter Island Oasis
4 bedrooms
4 bathrooms
Sleeps 5
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Mid-century on idyllic pasture like setting with pond
3 bedrooms
2 bathrooms
Sleeps 5
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Spacious beach house with stunning water views
5 bedrooms
5 bathrooms
Sleeps 10
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Views-Views-Views of beautiful Peconic Bay. Tastefully renovated 1929 Cape.
4 bedrooms
3 bathrooms
Sleeps 7
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Contemporary Home on Quiet Country Road/Walk to beach and Fresh Pond
3 bedrooms
2 bathrooms
Sleeps 7
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Landscaped Shelter Island Cottage with Pool
3 bedrooms
2 bathrooms
Sleeps 6
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
4 bedrooms
4 bathrooms
Sleeps 2
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Gorgeous, tranquil 9000 Sq Ft home on Dering Harbor
6 bedrooms
10 bathrooms
Sleeps 12
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New Listing: Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge...
4 bedrooms
3 bathrooms
Sleeps 8
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Romantic Shelter Island Cottage w/2 Pools & Pond
1 bedroom
2 bathrooms
Sleeps 5
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Shelter Island, NY Fully Renovated Farmhouse with Pool
3 bedrooms
2 bathrooms
Sleeps 8
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Luxurious 'Shelter Island Hideaway' w/ Pool!
4 bedrooms
4 bathrooms
Sleeps 10
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Summer Sun and Family Fun in Shelter Island
4 bedrooms
3 bathrooms
Sleeps 8
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The Ultimate Beach House
7 bedrooms
5 bathrooms
Sleeps 15
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Waterfront Charmer on idyllic Shelter Island
3 bedrooms
3 bathrooms
Sleeps 8
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Hilo Shores, bay access, air conditioned , rec room, spotless , family ready!!
3 bedrooms
3 bathrooms
Sleeps 6
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Charming 4 Bed/2.5 Bath Cottage In Historic Shelter Island, Walk To Ferry
4 bedrooms
2 bathrooms
Sleeps 8
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New Listing: Rustic Chic Designer Home on Dering Harbor, Private Dock &...
3 bedrooms
3 bathrooms
Sleeps 8
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Family friendly home near beach with wonderful deck!
4 bedrooms
2 bathrooms
Sleeps 7
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Bright and Airy West Neck Bay Shingle Style House
3 bedrooms
3 bathrooms
Sleeps 10
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Lovely property near beaches and amenities
3 bedrooms
2 bathrooms
Sleeps 6
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Shelter Island Home with water view and beach access!
3 bedrooms
3 bathrooms
Sleeps 5
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A FAMILY’S DREAM & THE DEFINITION OF SERENITY
4 bedrooms
3 bathrooms
Sleeps 10
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Cozy Cottage for 2 - great for couples/singles - in the heart of Shelter Island!
1 bedroom
1 bathroom
Sleeps 2
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New Renovation Waterfront House With Dock. Best Location In Shelter Island
3 bedrooms
3 bathrooms
Sleeps 8
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Pristine renovated home within minutes of West Neck harbor
3 bedrooms
3 bathrooms
Sleeps 6
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Resort Style Home- Family Friendly
4 bedrooms
3 bathrooms
Sleeps 6
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Stunning Shelter Island Estate
8 bedrooms
8 bathrooms
Sleeps 14
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Chic Shelter Island Home, Pool and Gardens
3 bedrooms
2 bathrooms
Sleeps 6
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New to market, House with pool and walk to beach
4 bedrooms
4 bathrooms
Sleeps 8
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Spacious house next to the beach, Ferry and Eateries.
6 bedrooms
5 bathrooms
Sleeps 11
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WATERFRONT with Private Beach Boat Dock and Launch Ramp Sleeps 7
2 bedrooms
3 bathrooms
Sleeps 7
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