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.
The Wayne Inn

The Wayne Inn

2 out of 5
Price was CA $1,614, price is now CA $884 per person
CA $884
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
6.8/10 (291 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,237, price is now CA $1,990 per person
CA $1,990
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,004 reviews)
We love 1Hotel. This was our fourth visit. However, this visit was different. From the loud music playing until two oclock in the morning, to the garbage left behind outside the entrance to the nightclub, the vibe was not at all what we experienced previously during our trips to Brooklyn. We sincerely hope the decision to use the upstairs floor as a nightclub is reconsidered. Being kept awake by loud music is not acceptable. Also, there was a bag of trash sitting on top of the trashcan for two days.Such a shame for this beautiful hotel. Attention to detail is what made this hotel so special.

Reviewed on May 10, 2026

Heritage Hotel

Heritage Hotel

2.5 out of 5
Manhattan
Price was CA $1,791, price is now CA $1,171 per person
CA $1,171
per person
Jul 20 - Jul 24
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very Good! (1,753 reviews)
Neat clean & tidy, great location close to everything including subway stations and great eateries/bars. Great price and staff. Would stay again.

Reviewed on May 11, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,845, price is now CA $1,210 per person
CA $1,210
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
The hotel was nice, room was very clean, bed was comfortable. The mini-fridge in the room was purely a minibar with no room for storage (and the door was stuck when I tried to use it). I didn’t ask about this, but it’s something to mention that was unexpected.

Reviewed on May 8, 2026

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Manhattan
Price was CA $1,354, price is now CA $894 per person
CA $894
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (6,856 reviews)
Rooms were not clean. Dusty floors, showers and fixtures like lamps and table ( I had a suite) . The couch in the suite was horrible. The shower was broken so I had to rig it to use it. They don’t have smart tvs! That is a must in 2026. For the money I expected better with cleanliness. Otherwise everything else was standard nothing exceptional

Reviewed on May 12, 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
Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Mashomack Preserve.

Find hotels in Menantic Creek

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 $769 per night from May 27 to May 28
CA $769
CA $1,055 total
May 27 - May 28
includes taxes & fees
8.4/10 Very Good! (778 reviews)
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 May 11, 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 $207 per night from May 26 to May 27
CA $207
CA $263 total
May 26 - May 27
includes taxes & fees
9.2/10 Wonderful! (1,343 reviews)
Cute place great views would go back in the summer

Reviewed on May 11, 2026

Montauk Manor
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
The price is CA $431 per night from May 26 to May 27
CA $431
CA $648 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Unhinged wacko

Reviewed on May 6, 2026

Montauk Yacht Club
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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.