Shelter Island, NY

Travel Guide

A coastal landscape with a lake, dense greenery, and a sunset sky.
A large house with a dock extending into a calm body of water, surrounded by trees and other houses.
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 gazebo on a rock by a river, surrounded by dense forest and a wooden fence.

Visit Shelter Island for nature trails, local wineries, and charming beaches that create memorable moments for every traveler.

Shelter Island is an ideal destination for outdoor and romantic travelers. You can explore the Mashomack Preserve, which offers various trails and natural habitats, or enjoy a round of golf at Gardiner's Bay Country Club. Wades Beach provides a relaxing spot by the water where you can unwind. Additionally, you might want to try your hand at mini-golf at Shelter Island Whale's Tail, or visit nearby attractions like the Greenport Carousel and several wineries such as Kontokosta Winery and The Old Field Vineyards.

Take time to wander through nearby areas that each present unique experiences. Dering Harbor and Greenport are known for romance and outdoor activities, with Greenport featuring the Railroad Museum of Long Island and the East End Seaport Maritime Museum. Shelter Island Heights, recognized for family-friendly experiences, hosts Crescent Beach and the historic Sylvester Manor, along with the Shelter Island Country Club for golf. Each area offers something distinctive while sharing a focus on outdoor enjoyment.

The best time to visit Shelter Island is from June to September, when the weather is mild and mostly dry, making it pleasant for outdoor activities. However, this period also sees higher visitor numbers, particularly from June to August. If you prefer a quieter experience, consider visiting from October to December when the demand is lower, allowing for a more relaxed atmosphere while enjoying the island's features.

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 Shell 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 Mashomack Preserve, some noteworthy sights in the nearby area.

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 Shelter Island Historical Society.

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 Shell Beach.

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$415 nightly
The price is $474 total per night from Nov 18 to Nov 19
$474 total
Nov 18 - Nov 19
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 ...
Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
$82 nightly
The price is $95 total per night from Nov 15 to Nov 16
$95 total
Nov 15 - Nov 16
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. ...
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $170 total per night from Nov 23 to Nov 24
$170 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,009 reviews)
"Great location. The restaurant / bistro is very good. Try the salmon. Staff accommodating and helpful. Room and facilities were clean and inviting. Would stay again."

Reviewed on Nov 9, 2026

Water's Edge Resort & Spa
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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
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway Amagansett NY
Book a stay at this beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Windward Shores Ocean Resort
Montauk Oceanside Suites

Montauk Oceanside Suites

3 out of 5
115 South Emerson Avenue Montauk NY
Stay at this aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point Lighthouse and Montauk Point are ...
Montauk Oceanside Suites
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 close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
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.
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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

An aerial view of a lighthouse on a rocky island surrounded by calm sea.

East Hampton

A pebbled beach at sunset with the sun setting over the horizon.

Greenport

A marina with several boats docked, a community bandstand, and a restaurant named American Legion.

Sag Harbor

A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights

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