Shelter Island Vacations from NT$33,138

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
Price was NT$37,352, price is now NT$33,138 per person
NT$33,138
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Newark Liberty Intl. Airport (EWR)
6/10 (2,187 reviews)
Good value, clean room, plenty of parking

Reviewed on 2026/5/18

Windrose On Hudson

Windrose On Hudson

3 out of 5
Price was NT$43,503, price is now NT$33,694 per person
NT$33,694
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (136 reviews)
Great location for quiet, serene and beautiful scenery.

Reviewed on 2026/5/17

HYATT house White Plains

HYATT house White Plains

3 out of 5
Price was NT$50,977, price is now NT$44,752 per person
NT$44,752
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to New York (JFK)
8.8/10 Excellent! (1,039 reviews)
Comfortable and clean. The breakfast was abundant and we enjoyed the restaurant area long past breakfast and staff was very accommodating.

Reviewed on 2026/5/20

Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

3 out of 5
Price was NT$39,358, price is now NT$35,999 per person
NT$35,999
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to New York (JFK)
7.8/10 Good! (1,009 reviews)
Old building but overall good experience. Nice staff. The hallways have specific lemon smell of cleaning solution. Please do not use strong smelling cleaning solutions. Thanks

Reviewed on 2026/5/17

Days Inn by Wyndham Nanuet / Spring Valley

Days Inn by Wyndham Nanuet / Spring Valley

2 out of 5
Price was NT$38,077, price is now NT$34,987 per person
NT$34,987
per person
Jun 23 - Jun 27
found 1 day ago
Roundtrip flight included
Port of Spain (POS) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,000 reviews)
Clean room and pleasant staff

Reviewed on 2026/5/13

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 Crescent Beach.

Find hotels in Menantic Creek

Find the Best Shelter Island Vacation Packages

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 center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers 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.

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 NT$19,789 per night from May 31 to Jun 1
NT$19,789
NT$27,130 total
May 31 - Jun 1
includes taxes & fees
8.2/10 Very Good! (781 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 2026/5/11

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is NT$8,520 per night from Jun 1 to Jun 2
NT$8,520
NT$10,354 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (1,347 reviews)
"Very cool, classic hotel"

Reviewed on 2026/5/19

Montauk Manor
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 NT$2,621 per night from May 21 to May 22
NT$2,621
NT$3,014 total
May 21 - May 22
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"We have been coming here for years and it is the best it’s ever been! Staff is friendly and accommodating. The rooms have been renovated and clean."

Reviewed on 2026/5/17

Pier Blue Inn Old Saybrook - Essex
See all 4,775 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.

Discover the most popular places to visit in Shelter Island

Colorful pebbles and shells on a beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach

Shelter Island Historical Society

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

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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.