Shelter Island Holidays

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Shelter Island Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Long Island - Garden City

Red Roof Inn PLUS+ Long Island - Garden City

2.5 out of 5
Price was S$647, price is now S$526 per person
S$526
per person
9 May - 11 May
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
7.2/10 Good! (1,418 reviews)
Very quiet and clean

Reviewed on 25 Mar, 2026

Pod Brooklyn

Pod Brooklyn

3 out of 5
Price was S$820, price is now S$669 per person
S$669
per person
8 May - 11 May
found 1 day ago
Return flight included
Raleigh (RDU) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,796 reviews)
Only thing was, I did ask for housekeeping the night before twice, but I never got my rooms clean

Reviewed on 29 Mar, 2026

Hotel 1080 Brooklyn

Hotel 1080 Brooklyn

3.5 out of 5
Price was S$817, price is now S$675 per person
S$675
per person
8 May - 11 May
found 1 day ago
Return flight included
Raleigh (RDU) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (713 reviews)
Wish we had known that one wall of the shower was a window into the room. It was frosted up to my waist, which would be fine for a man, but very awkward for a female sharing a room with 2 sons. Other than that, the room was very clean and the staff were friendly. The neighborhood was pretty sketchy after dark. So walking 5 minutes from the subway at night was a little concerning.

Reviewed on 29 Mar, 2026

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Find hotels in Silver Beach

Shelter Island Beach Holiday

There's nothing like a Shelter Island holiday to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Top hotels in Shelter Island

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 S$891 per night from 16 Apr to 17 Apr
S$891
16 Apr - 17 Apr
includes taxes & fees
8.4/10 Very Good! (749 reviews)
Absolutely beautiful property- laid back but classically tasteful. Staff was wonderful…Mimmeo & Sebastian are fabulous & friendly & Ivette in the spa gave a top notch massage. Gigi’s never disappointed! I will absolutely be back.

Reviewed on 27 Mar, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is S$248 per night from 13 Apr to 14 Apr
S$248
13 Apr - 14 Apr
includes taxes & fees
9.2/10 Wonderful! (1,309 reviews)
Went for a quick one both stay with my kids to go hiking. We picked this place because they had a pool. Everything was clean and nice. The rooms were cool the kids loved it

Reviewed on 28 Mar, 2026

Montauk Manor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is S$349 per night from 6 Apr to 7 Apr
S$349
6 Apr - 7 Apr
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Enjoyable stay.

Reviewed on 28 Mar, 2026

Water's Edge Resort & Spa
See all 4,755 properties in Shelter Island
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.