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.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,147 per person
CA $1,147
per person
Jun 3 - Jun 7
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,852 reviews)
Complementary pastry amazing. Staff was absolutely fantastic…professional and nice.

Reviewed on Apr 9, 2026

The Ned NoMad

The Ned NoMad

5 out of 5
Manhattan
Price was CA $3,084, price is now CA $1,708 per person
CA $1,708
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (119 reviews)
Room was great staff not so good

Reviewed on Feb 15, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,614, price is now CA $2,075 per person
CA $2,075
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (659 reviews)
Great location. Great views in the Towers.

Reviewed on Mar 17, 2026

WestHouse New York

WestHouse New York

5 out of 5
Manhattan
Price was CA $2,956, price is now CA $1,779 per person
CA $1,779
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,003 reviews)
Great staff, amazing lunch and breakfast

Reviewed on Apr 9, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was CA $2,449, price is now CA $1,501 per person
CA $1,501
per person
Jun 3 - Jun 7
found 6 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,764 reviews)
The location of this hotel could not be better if you want to be close to Central Park. The only breakfast option is a $75 buffet (no thanks). There was no cocktail bar for a nightcap, the rooms were a bit tired and the air conditioning could not get the room below a humid 72, so our sleep was terrible.

Reviewed on Apr 7, 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 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 $704 per night from Apr 16 to Apr 17
CA $704
CA $965 total
Apr 16 - Apr 17
includes taxes & fees
8.4/10 Very Good! (753 reviews)
WE HAD A LOVELY WEEKEND. SERVICE WAS EXCELLENT.

Reviewed on Apr 6, 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 $209 per night from May 12 to May 13
CA $209
CA $266 total
May 12 - May 13
includes taxes & fees
9.2/10 Wonderful! (1,318 reviews)
Beautiful room, beautiful property, great shuttle service to town.

Reviewed on Apr 10, 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 $329 per night from Apr 14 to Apr 15
CA $329
CA $402 total
Apr 14 - Apr 15
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Yes, we found everything we needed.

Reviewed on Apr 7, 2026

Water's Edge Resort & Spa
See all 4,730 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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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.