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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, (25)
The price is SAR 360
SAR 684 total
includes taxes & fees
17 Apr - 18 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)

Hampton Cottage.
Hampton Cottage.
10.0 out of 10, Exceptional, (4)
The price is SAR 897
SAR 1,385 total
includes taxes & fees
27 Apr - 28 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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Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
10.0 out of 10, Exceptional, (41)
The price is SAR 3,002
SAR 5,389 total
includes taxes & fees
9 May - 10 May

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1155)
The price is SAR 557
SAR 710 total
includes taxes & fees
5 May - 6 May

Montauk Oceanside Suites
Montauk Oceanside Suites
8.6 out of 10, Excellent, (369)
The price is SAR 511
SAR 624 total
includes taxes & fees
29 Apr - 30 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
2 day getaway
"The experience was very good. everything was what I expected. only thought was the $25 parking was a bit much"
A verified traveler stayed at The Harbor Front Inn
Posted 12 hours ago
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