Shelter Island

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 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 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.

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

Menantic Creek

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

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

Coecles Harbor

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

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

Hay Beach

When in Hay Beach, you can plan a visit to Greenport Carousel and Greenport Harbor Brewing Company, some noteworthy sights in the nearby area.

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 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 Shelter Island Historical Society.

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 RM365 per night from 30 Aug to 31 Aug
RM365
RM419 total
30 Aug - 31 Aug
includes taxes & fees
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. ...
8/10 Very good! (1,002 reviews)
"My room smelled like urine and the lobby smelled like a wet dog. Bathroom was dim and dingy, ironing board stained, A/C vents were full of dust and didn’t work well. TV didn’t work either. How they can charge $150 for a room here is appalling. The front sign is the only thing nice about the property- ..."

Reviewed on 28 Aug 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is RM1,180 per night from 15 Sept to 16 Sept
RM1,180
RM1,693 total
15 Sept - 16 Sept
includes taxes & fees
Stay at this beach hotel in Greenport. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
Sound View Greenport
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is RM1,554 per night from 7 Sept to 8 Sept
RM1,554
RM2,235 total
7 Sept - 8 Sept
includes taxes & fees
Stay at this hotel in Montauk. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Montauk Point Lighthouse and Montauk Point are located ...
9.2/10 Wonderful! (188 reviews)
"Beautiful property in an excellent location. Across the street from a beautiful beach where there are very helpful and friendly staff to set up your beach chairs and umbrellas. The hotel feels new with a beautiful wellness center with showers, a gym, saunas and cold plunges. The rooms are very clean ..."

Reviewed on 27 Aug 2026

Offshore Montauk
See all 4,706 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.
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
North Fork Resort
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 ...
9.2/10 Wonderful! (1,393 reviews)
"I really liked the hotel. They were friendly and knowledgeable. Breakfast was good and healthy. The jacuzzi was just what I needed. Shuttle service was very good. Loved the deer spotting and sunset viewing. Very good room service."

Reviewed on 26 Aug 2026

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 ...
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

10.0/10 (1 review)
Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties

Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

RM716
per adult
Sunday Brunch Sail in Greenport
Private Vacation Photoshoot with Photographer in The Hamptons

Private Vacation Photoshoot with Photographer in The Hamptons

RM1,159
per adult
Private Vacation Photoshoot with Photographer in The Hamptons
See all activities in Shelter Island