Shelter Island Travel Guide

Tourist Guide

Photo by tom owens
Photo by Rich Barton

Where to stay in Shelter Island

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Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Silver Beach
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Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Coecles Harbor
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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Menantic Creek
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Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Hay Beach
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Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Mashomack Preserve and Sunset Beach.

Shorewood
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Montclair Colony

If you're looking for some top things to see and do in Montclair Colony and surrounding area, you can visit Sunset Beach and Crescent Beach.

Montclair Colony
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 Rp6.510.660 per night from 12 Jan to 13 Jan
Rp6.510.660
Rp8.926.115 total
12 Jan - 13 Jan 2026
includes taxes & fees
Stay at this beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Popular attractions Hither Woods Preserve and Hither Hills ...
8.2/10 Very Good! (701 reviews)
Everything was perfect. Staff, room, experience. Will definitely stay again.

Reviewed on 14 Dec 2025

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
The price is Rp3.039.830 per night from 21 Dec to 22 Dec
Rp3.039.830
Rp3.783.776 total
21 Dec - 22 Dec
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,004 reviews)
Holiday family tradition!

Reviewed on 12 Dec 2025

Water's Edge Resort & Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.8/10 Good! (1,001 reviews)
Clean and pleasant place staff is accommodating and professional a good value on the shoreline

Reviewed on 10 Dec 2025

Pier Blue Inn Old Saybrook - Essex
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.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,268 reviews)
The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable

Reviewed on 15 Dec 2025

Montauk Manor
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
8.8/10 Excellent! (249 reviews)
The unit was cute and well-appointed. I would recommend a new refrigerator in the unit, as the freezer door was broken.

Reviewed on 12 Nov 2025

Cliffside Resort Condominiums
Driftwood Resort

Driftwood Resort

3.5 out of 5
2178 Montauk Highway Montauk NY
Stay at this beach condo in Montauk. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Walking Dunes Trailhead and Hither Hills State Park ...
8.8/10 Excellent! (236 reviews)
The room was beautiful and very clean. The pool was wonderful and so warm. We also used the tennis courts. I would highly recommend this hotel!!!!

Reviewed on 1 Oct 2025

Driftwood Resort
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.

Popular places to visit

Things to do