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
$149 nightly
The price is $171 total per night from Nov 1 to Nov 2
$171 total
Nov 1 - Nov 2
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 ...
9.2/10 Wonderful! (64 reviews)
"The only real problem was the constant loud noise of air rushing outside the room from an air shaft along side the chimney. The staff was not able to quiet it. Most of the noise came in via the window a/c unit so removing it and closing the window would have helped. There refrigerator was warm when ..."

Reviewed on Sep 27, 2026

The Chequit
The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
Book a stay at this beach hotel in Shelter Island Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Get rates
The Pridwin Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
$78 nightly
The price is $90 total per night from Oct 8 to Oct 9
$90 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. ...
Pier Blue Inn Old Saybrook - Essex
See all 4,670 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
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! (61 reviews)
"Fantastic contemporary cottage. Looks brand new and it has everything. Wonderful place to stay. Check in process needs improvement with more attention paid to details by staff."

Reviewed on Sep 29, 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 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.
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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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