A wooden gazebo by a pond with a large tree trunk nearby.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Shelter Island condo rentals

Room

1. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (252 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
$158 nightly
The price is $181
Oct 5 - Oct 6
Total with taxes and fees
Driftwood Resort
A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.

2. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
8.4 out of 10, Very good, (5 reviews)
"⭐⭐⭐⭐⭐ We had such a wonderful stay at Offshore Montauk! The hotel is beautifully designed, incredibly clean, and the location couldn’t be better—just steps from the beach and an easy walk to Montauk’s restaurants and shops. The rooms are stylish, comfortable, and so peaceful. We especially loved the pool, sauna, and cold plunge—they were the perfect way to relax and recharge after a day at the beach. Most importantly, the staff was genuinely welcoming and made us feel at home from the moment we...
United States
Iryna
$568 nightly
The price is $649
Oct 5 - Oct 6
Total with taxes and fees
Offshore Spa & Residences
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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Top Shelter Island Hotel Reviews

Zey Hotel

Zey Hotel

10/10 Excellent
"Adorable, comfy, clean , and convenient with friendly staff."
Nina 2-night trip
Posted 16 hours ago
Zey Hotel

Find out more about Shelter Island

Shelter Island Condo Rentals information

Number of reviews
Accommodation
24 Condo Rentals
Lowest Price
$181
Highest Price
$649

Frequently asked questions

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