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. Learn more about Shelter Island
Learn more about Shelter Island
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 Sunset Beach and Crescent 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 Shelter Island Historical Society 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 Shelter Island Historical Society and Mashomack Preserve, 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 Greenport Carousel and Greenport Harbor Brewing Company 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 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
$80 nightly
The price is $93 total per night from Oct 8 to Oct 9
$93 total
Oct 8 - Oct 9
Total with taxes and 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! (1,005 reviews)
"Nothing fancy, but clean and nice!"

Reviewed on Sep 19, 2026

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
$430 nightly
The price is $491 total per night from Sep 29 to Sep 30
$491 total
Sep 29 - Sep 30
Total with taxes and 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 ...
8.2/10 Very Good! (859 reviews)
"Went for an overnight mid September and it was so lovely. Spa and pool gorgeous. They do charge a fee for booking with expedia which brings the price up to what they offer on their website which we did not know about."

Reviewed on Sep 19, 2026

Gurney's Montauk Resort & Seawater Spa
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$264 nightly
The price is $302 total per night from Oct 14 to Oct 15
$302 total
Oct 14 - Oct 15
Total with taxes and fees
Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (731 reviews)
"Nice property clean rooms unique having room right on the ocean front was surprised by a pretty nice breakfast many choices food coffee which is always important overall the property is well located to visit surrounding farms and vineyards and short car ride to restaurants and water front"

Reviewed on Sep 19, 2026

Sound View Greenport
See all 4,644 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' ...
9.6/10 Exceptional! (56 reviews)
"Very new and clean property very helpful and friendly staff ..... some areas where the rvs are the view not great ..... otherwise all good"

Reviewed on Sep 18, 2026

North Fork Resort
The Surf Club

The Surf Club

3.5 out of 5
20 Surfside Avenue Montauk NY
Book a stay at this beach aparthotel in Montauk. Enjoy free WiFi, a beach locale, and room service. Popular attractions Montauk Point Lighthouse and Montauk ...
The Surf Club
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 carefree 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

$175
per adult
Sunday Brunch Sail in Greenport
See all activities in Shelter Island

Frequently asked questions

Is Shelter Island worth visiting?
Shelter Island is worth visiting for its beautiful Wades Beach and the Gardiner's Bay Country Club. Travelers can also enjoy a variety of dining experiences, with options ranging from classic North American dishes to fresh seafood. It offers a relaxed atmosphere for those looking to enjoy coastal activities and local flavors.
When is the best time to visit Shelter Island?
The best time to visit Shelter Island is from June through August, when it's most popular with travelers. For fewer crowds and better value, the quieter months of October through December are a good option, offering a more relaxed experience.
What is Shelter Island known for?
Shelter Island is known for its recreational spots like Gardiner's Bay Country Club, offering golf and leisure. Travelers also enjoy its natural beauty at Wades Beach and the Mashomack Preserve, which provides a peaceful setting for outdoor activities on this island in the United States.
What is a good itinerary length for Shelter Island?
A good itinerary length for Shelter Island is two to three days to enjoy highlights like Wades Beach and Mashomack Preserve. For a more relaxed trip, or to include activities at Gardiner's Bay Country Club, consider an extended stay of four to five days.
What are the top things to do in and around Shelter Island?
Shelter Island offers beautiful natural escapes and unique local landmarks:


How do I plan a trip to Shelter Island?
Start planning your Shelter Island trip by searching Expedia for hotels, flights, and rental cars. Book popular activities like Gardiner's Bay Country Club, Wades Beach, and Mashomack Preserve in advance. Always have indoor backup plans for outdoor activities, ensuring weather flexibility.
What cuisines can you find in Shelter Island?
In Shelter Island you can find Italian cuisine, offering classic dishes such as pasta, pizza, and tiramisu. Travelers can also enjoy fresh seafood, North American comfort foods, and a variety of Asian and European dishes, providing diverse dining options.
Can I book a refundable hotel in Shelter Island?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Shelter Island by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Shelter Island with Expedia?
Expedia makes it easier to plan your Shelter Island trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Shelter Island?
The best choice depends on your travel style. Hotels in Shelter Island can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Shelter Island trip on Expedia?
Once you've booked your Shelter Island trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Shelter Island trip?
Expedia offers customer support before, during, and after your Shelter Island trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Shelter Island?
If it's your first trip to Shelter Island, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Shelter Island hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Shelter Island hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Shelter Island

A sandy beach with wooden fences and houses on a dune.

East Hampton

An aerial view of a harbor with boats, a ship, and a dock extending into the water.

Greenport

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

Sag Harbor

A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights

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