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Search Chalets in Shelter Island

February 2025

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Browse Select Shelter Island Chalets

Spectacular 5 acre secluded private gem

Spectacular 5 acre secluded private gem
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

3.5 star property
9.2 out of 10, Wonderful, (1115)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is CA $186
CA $240 total
includes taxes & fees
Feb 25 - Feb 26
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is CA $159
CA $196 total
includes taxes & fees
Feb 27 - Feb 28
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is CA $187
CA $244 total
includes taxes & fees
Feb 20 - Feb 21
Windward Shores Ocean Resort
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.