Shelter Island Heights, NY

Travel Guide

A pebbled beach with a sunset and a distant bridge.
A lake with houses on the shore, surrounded by trees and a clear sky.
A coastal landscape with a sunset, a marina, and a residential area.
A marina with numerous sailboats docked, a large tree in the foreground, and a flagpole with an American flag.
A calm lake reflecting trees and a clear sky.

Where to stay in Shelter Island Heights

Find the best Shelter Island Heights areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island Heights
Learn more about Shelter Island Heights
A calm lake reflecting trees and a clear sky.
Photo by Erisa Dilo
Open Photo by Erisa Dilo

The Heights

If you're spending some time in The Heights, Sunset Beach and Shelter Island Country Club are top sights worth seeing.

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.

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
$163 nightly
The price is $186 total per night from Nov 23 to Nov 24
$186 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and premium bedding. Popular attractions Shelter Island Country Club and Sunset ...
The Chequit
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$422 nightly
The price is $482 total per night from Nov 8 to Nov 9
$482 total
Nov 8 - Nov 9
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! (873 reviews)
"Always an amazing stay at Gurneys. The ocean views and the restorative spa alone make this place so special. The staff is friendly and the rooms are kept so clean. Highly recommended."

Reviewed on Oct 23, 2026

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
$220 nightly
The price is $253 total per night from Nov 23 to Nov 24
$253 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! (1,001 reviews)
"Great"

Reviewed on Oct 21, 2026

Water's Edge Resort & Spa
See all 4,665 properties in Shelter Island Heights
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 ...
8.6/10 Excellent! (457 reviews)
"Really loved the location of this lodging. We were within walking distance to the town and to the beach."

Reviewed on Oct 19, 2026

Montauk Oceanside Suites
See all properties in Shelter Island Heights
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 Heights attractions

Sunset Beach

9.4/10 (14 reviews)
Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
See properties

Frequently asked questions

Is Shelter Island Heights worth visiting?
Shelter Island Heights is worth visiting for its beautiful coastal scenery and inviting beaches. Travelers can relax and enjoy the natural beauty at places like Sunset Beach and Crescent Beach, which are perfect for unwinding by the water and enjoying outdoor activities.
When is the best time to visit Shelter Island Heights?
The best time to visit Shelter Island Heights is from May through July, when the weather is typically warm and pleasant for enjoying the area. For fewer crowds and better value, the quieter months of November through January are a good option, offering a cooler experience.
What is Shelter Island Heights known for?
Shelter Island Heights is known for its inviting shores, including Sunset Beach and Crescent Beach, which offer travelers relaxing experiences. It is also home to Sylvester Manor, a historic site, providing a glimpse into the area's past.
What is a good itinerary length for Shelter Island Heights?
A good itinerary length for Shelter Island Heights is two to three days to enjoy highlights like Sunset Beach, Crescent Beach, and explore Sylvester Manor. For a more relaxed trip, or to spend more time at the beaches and exploring the area, consider an extended stay of four to five days.
What are the top things to do in and around Shelter Island Heights?
Shelter Island Heights features lovely beaches, a historic manor, and a place for golf:


How do I plan a trip to Shelter Island Heights?
To plan your trip to Shelter Island Heights, search for places to stay on Expedia. Book flights and rental cars in advance, especially for peak times. Plan to visit attractions like Sunset Beach, Crescent Beach, and Sylvester Manor. Remember to pair outdoor plans with indoor backups for weather flexibility during your stay.
Can I book a refundable hotel in Shelter Island Heights?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Shelter Island Heights 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 Heights with Expedia?
Expedia makes it easier to plan your Shelter Island Heights 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 Heights?
The best choice depends on your travel style. Hotels in Shelter Island Heights 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 Heights trip on Expedia?
Once you've booked your Shelter Island Heights 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 Heights trip?
Expedia offers customer support before, during, and after your Shelter Island Heights 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 Heights?
If it's your first trip to Shelter Island Heights, 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 Heights 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 Heights 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 Heights

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

Greenport

A wooden gazebo by a pond with a large tree trunk nearby.

Shelter Island

A calm lake with a forest in the background during sunset.

Southold

A coastal landscape with a sandy beach, calm water, and scattered trees.

East Marion

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