Shelter Island Vacations

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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
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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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is NT$2,430 per night from Oct 6 to Oct 7
NT$2,430
NT$2,795 total
Oct 6 - Oct 7
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"Highly recommend!"

Reviewed on 2025/9/21

Pier Blue Inn Old Saybrook - Essex
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$14,270 per night from Sep 28 to Sep 29
NT$14,270
NT$19,476 total
Sep 28 - Sep 29
includes taxes & fees
8.2/10 Very Good! (668 reviews)
"Amazing resort, very friendly staff, food and drinks are Amazing! We enjoyed our stay."

Reviewed on 2025/9/15

Gurney's Montauk Resort & Seawater Spa
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is NT$4,536 per night from Oct 26 to Oct 27
NT$4,536
NT$5,182 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (141 reviews)
"Great hotel, nice staff, clean and i loved the beach access. Only downfall was the 1 bathroom when not checked intoba room. Long line and humid"

Reviewed on 2025/9/24

Montauk Blue Hotel
See all 4,719 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

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.