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Compare 1926 Vacation Homes in Shelter Island with updated reviews, rates, and availability.

10 Bedroom Hampton House with a regulation size Pickleball
10 Bedroom Hampton House with a regulation size Pickleball
10.0 out of 10, Exceptional, (25)

Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (98)

Waterfront House with picture-perfect views from all 3 levels.
Waterfront House with picture-perfect views from all 3 levels.
9.8 out of 10, Exceptional, (81)

Stunning New Designer Renovation
Stunning New Designer Renovation
9.4 out of 10, Exceptional, (21)

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, (129)

4-bedroom house is across the street from private beach and walk to town
4-bedroom house is across the street from private beach and walk to town

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (99)

Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
Secluded 1 Br Cottage on the Lake, Close to Ditch with OS Shower & Fabulous Yard
9.8 out of 10, Exceptional, (39)
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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Other property types in Shelter Island

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1145)
The price is SAR 536
SAR 685 total
includes taxes & fees
1 Apr - 2 Apr

Montauk Oceanside Suites
Montauk Oceanside Suites
8.6 out of 10, Excellent, (367)
The price is SAR 510
SAR 624 total
includes taxes & fees
1 Apr - 2 Apr

Windward Shores Ocean Resort
Windward Shores Ocean Resort
8.8 out of 10, Excellent, (275)
The price is SAR 494
SAR 646 total
includes taxes & fees
1 Apr - 2 Apr
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.
Recent reviews of Shelter Island hotels
Recent reviews of Shelter Island hotels

The Harbor Front Inn
5/5 Excellent
"Location "
A verified traveler stayed at The Harbor Front Inn
Posted 1 day ago
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