Shelter Island Holiday Packages

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Top Shelter Island hotels

Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is NZ$325 per night from 21 May to 22 May
NZ$325
21 May - 22 May
includes taxes & fees
Stay at this aparthotel in Montauk. Enjoy free Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
Cute place great views would go back in the summer

Reviewed on 11 May 2026

Opens in a new windowMontauk Manor
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is NZ$1,242 per night from 17 May to 18 May
NZ$1,242
17 May - 18 May
includes taxes & fees
Stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Popular attractions Hither Woods Preserve and Hither Hills ...
Stellar staff who made us feel most welcome. Loved the diversity of the team. Unforgettable scenery and experiences. We will definitely come back!

Reviewed on 11 May 2026

Opens in a new windowGurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is NZ$156 per night from 19 May to 20 May
NZ$156
19 May - 20 May
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
If you can look beyond the immediate exterior and sense of disrepair (it's not...), then you can enjoy the stay here. While there is no swimming pool, the property is well positioned to the coast and local beaches. They were doing some road construction immediately outside the property and on the ...

Reviewed on 15 May 2026

Opens in a new windowPier Blue Inn Old Saybrook - Essex
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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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