Shelter Island, NY

Travel Guide

A wooden gazebo by a pond with a large tree trunk nearby.
A sunset over a calm lake with a pier extending into the water, surrounded by trees and a road with a pedestrian crossing.
A large house with a dock extending into a calm body of water, surrounded by trees and other houses.
A gazebo on a rock by a river, surrounded by dense forest and a wooden fence.
A coastal landscape with a lake, dense greenery, and a sunset sky.

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most.
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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 Crescent Beach and Sunset Beach.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

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

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

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

A calm lake with reflections of clouds, surrounded by trees and a distant structure.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

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

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 ₩1,573,139 per night from Jul 8 to Jul 9
₩1,573,139
₩2,156,769 total
Jul 8 - Jul 9
includes taxes & fees
Book a 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 ...
8.4/10 Very Good! (816 reviews)
"Great experience."

Reviewed on Jun 25, 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is ₩1,052,852 per night from Jul 20 to Jul 21
₩1,052,852
₩1,378,239 total
Jul 20 - Jul 21
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...
9.2/10 Wonderful! (145 reviews)
"best staff"

Reviewed on Jun 28, 2026

Offshore Montauk
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is ₩136,901 per night from Jul 7 to Jul 8
₩136,901
₩157,436 total
Jul 7 - Jul 8
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,002 reviews)
"staff and parking"

Reviewed on Jun 22, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,734 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.
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
Montauk Manor
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
9.2/10 Wonderful! (25 reviews)
"We loved our stay at the North Fork Resort. We would definitely recommend. Family & pet friendly to the max! Any hiccups we had with our stay were resolved without hesitation or annoyance by the staff. They were incredibly accommodating. The pool area was spacious and clean but the pool itself was ..."

Reviewed on Jun 26, 2026

North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Book a stay at this beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
9/10 Wonderful! (263 reviews)
"Lovely condo, set back from the coast but gorgeous sea view. Brilliant covered external seating area which shades form the sun and the rain. Condo was very nicely decorated."

Reviewed on Jun 28, 2026

Cliffside Resort Condominiums
See all 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.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/5 (1 review)
Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
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Cities near Shelter Island

A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor