Shelter Island Vacation Packages

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Your Shelter Island Vacation

Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.

Top Shelter Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Newark Liberty International Airport Marriott

Newark Liberty International Airport Marriott

4 out of 5
Price was CA $2,307, price is now CA $1,437 per person
CA $1,437
per person
Apr 20 - Apr 27
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,010 reviews)
No pool but the staff and restaurants made

Reviewed on Mar 11, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was CA $2,649, price is now CA $1,498 per person
CA $1,498
per person
Apr 20 - Apr 27
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,003 reviews)
All staff we came into contact with from front desk to housekeeping to breakfast/happy hour to doormen were super attentive, very friendly and seemed to sincerely see us. The happy hour/dinner and breakfast provided surprisingly good food, lots of variety and very generous pours! Sonia was a standout and we looked forward to seeing her each evening. Beds and bedding very comfortable. Room nicely appointed and clean.

Reviewed on Mar 1, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $7,703, price is now CA $4,483 per person
CA $4,483
per person
Apr 20 - Apr 27
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,000 reviews)
Excellent staff, clean room, fantastic onsite restaurants.

Reviewed on Mar 10, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was CA $3,924, price is now CA $2,371 per person
CA $2,371
per person
Apr 20 - Apr 27
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,002 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $5,495, price is now CA $3,392 per person
CA $3,392
per person
Apr 20 - Apr 27
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
The staff was very friendly and the ambience was nice. However, the room was very cramped and had to be careful not to fall over columns and bed on the way to the bathroom. Walls were thin and there was no facial soap provided.

Reviewed on Mar 13, 2026

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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 might 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 Vacation

There's nothing like a Shelter Island vacation 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.

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Shelter Island Hotel Deals

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 CA $467 per night from Mar 22 to Mar 23
CA $467
CA $641 total
Mar 22 - Mar 23
includes taxes & fees
8.4/10 Very Good! (737 reviews)
I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly ...

Reviewed on Mar 4, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is CA $158 per night from Mar 16 to Mar 17
CA $158
CA $208 total
Mar 16 - Mar 17
includes taxes & fees
9.2/10 Wonderful! (1,302 reviews)
Always such a pleasure at the Manor.

Reviewed on Feb 28, 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 CA $184 per night from Apr 1 to Apr 2
CA $184
CA $235 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Excellent place to stay, water view

Reviewed on Mar 12, 2026

Water's Edge Resort & Spa
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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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Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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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.