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Compare 225 Cottages in Shelter Island with updated reviews, rates, and availability.

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage short walk to Chalker Beach
Charming 3-bedroom cottage short walk to Chalker Beach

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets
9.2 out of 10, Wonderful, (23)
The price is SAR 356
SAR 679 total
includes taxes & fees
6 Apr - 7 Apr

The gardners Cottage 1 mile from long Island Sound - pet friendly
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (13)

Enchanted Waterfront Cottage
Enchanted Waterfront Cottage
9.0 out of 10, Wonderful, (19)

Orient Village — Historic Bayfront Cottage — 2025 Season
Orient Village — Historic Bayfront Cottage — 2025 Season
10.0 out of 10, Exceptional, (20)
The price is SAR 4
SAR 1,125 total
includes taxes & fees
10 Apr - 11 Apr

Hampton Cottage.
Hampton Cottage.
10.0 out of 10, Exceptional, (3)
The price is SAR 784
SAR 1,103 total
includes taxes & fees
6 Apr - 7 Apr

'The Gate House'on Beach front Estate with Dockage. Walk to Village .
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
9.8 out of 10, Exceptional, (91)
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, (1143)
The price is SAR 536
SAR 685 total
includes taxes & fees
14 Apr - 15 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
9 Apr - 10 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
8 Apr - 9 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

Hyatt Place Long Island East End
5/5 Excellent
"amazing would definitely stay again thank you! "
A verified traveler stayed at Hyatt Place Long Island East End
Posted 17 hours ago
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