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Shelter Island Vacation Rentals
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Our top choices for Shelter Island vacation homes

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
9.6 out of 10, Exceptional, (13)
The price is CA $443
CA $824 total
includes taxes & fees
Aug 27 - Aug 28

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
9.6 out of 10, Exceptional, (133)

Direct waterfront vacation rental, family friendly, pets allowed
Direct waterfront vacation rental, family friendly, pets allowed
10.0 out of 10, Exceptional, (71)

Stunning Hampton Holiday Family Fantasy for your Team
Stunning Hampton Holiday Family Fantasy for your Team
9.8 out of 10, Exceptional, (69)

Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
Comfortable Orchard Oasis in wine country on Long Islands beautiful North Fork!
10.0 out of 10, Exceptional, (6)

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen
10.0 out of 10, Exceptional, (93)

Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
Charming East Hampton Cottage with Lush Gardens & Indoor-Outdoor Living
10.0 out of 10, Exceptional, (2)

Exquisite New Hampton Home in a Perfect Location
Exquisite New Hampton Home in a Perfect Location
10.0 out of 10, Exceptional, (4)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa
10/10 Excellent
Find out more about Shelter Island
Find out more about Shelter Island
Shelter Island Vacation Homes information
Number of reviews | 716 |
---|---|
Accommodation | 1993 Vacation Homes |
Lowest Price | CA $265 |
Highest Price | CA $1,112 |
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