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Search Chalets in Shelter Island

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Shelter Island Chalets

Spectacular 5 acre secluded private gem
Smart TV, fireplace, table tennis

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
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1144)
"the location is great and price is reasonable. "
The price is CA $177
CA $230 total
includes taxes & fees
Apr 17 - Apr 18
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (367)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is CA $195
CA $238 total
includes taxes & fees
Apr 2 - Apr 3
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (275)
"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 $189
CA $247 total
includes taxes & fees
Apr 2 - Apr 3
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.