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Compare 230 Cottages in Shelter Island Heights 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 334
SAR 653 total
includes taxes & fees
31 Mar - 1 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 Heights

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1146)
The price is SAR 536
SAR 685 total
includes taxes & fees
31 Mar - 1 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
31 Mar - 1 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
31 Mar - 1 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 Heights hotels
Recent reviews of Shelter Island Heights hotels

Water's Edge Resort & Spa
5/5 Excellent
Excellent stay
"It was a lovely one night stay with a friend. The room was beautiful, the hotel was stunning, and the check in was great. Lots of recommendations for good places to go. Very pleasant experience!"
A verified traveler stayed at Water's Edge Resort & Spa
Posted 4 days ago
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