Shelter Island Travel Guide

Tourist Guide

Photo by tom owens
Photo by tom owens
Photo by Rich Barton
Photo by Rich Barton

Where to stay in Shelter Island

Default Image

Menantic Creek

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

Menantic Creek
Default Image

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.

Silver Beach
Default Image

Coecles Harbor

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

Coecles Harbor
Default Image

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Hay Beach
Default Image

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 Sunset Beach.

Shorewood
Default Image

Montclair Colony

If you're looking for some top things to see and do in Montclair Colony and surrounding area, you can visit Sunset Beach and Crescent Beach.

Montclair Colony
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 ฿2,599 per night from 12 Oct to 13 Oct
฿2,599
฿2,989 total
12 Oct - 13 Oct
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. ...
7.8/10 Good! (1,005 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."

Reviewed on 4 Oct 2025

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
The price is ฿10,099 per night from 30 Oct to 31 Oct
฿10,099
฿13,783 total
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa and 2 restaurants. Our guests praise the room service in their reviews. ...
8.2/10 Very Good! (669 reviews)
"wonderful place only criticism is how far away rooms are from lobby and the rest of the facilities"

Reviewed on 29 Sept 2025

Gurney's Montauk Resort & Seawater Spa
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is ฿3,034 per night from 3 Nov to 4 Nov
฿3,034
฿3,489 total
3 Nov - 4 Nov
includes taxes & fees
Stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"

Reviewed on 5 Oct 2025

Quality Inn Old Saybrook - Westbrook
See all 4,713 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.
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (296 reviews)
"The non ocean view rooms are fabulous. I’m sure the ocean side ones are great."

Reviewed on 30 Sept 2025

Windward Shores Ocean Resort
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
Stay at this 3.5-star 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 ...
9/10 Wonderful! (1,253 reviews)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay."

Reviewed on 6 Oct 2025

Montauk Manor
Montauk Oceanside Suites

Montauk Oceanside Suites

3 out of 5
115 South Emerson Avenue, Montauk, NY
Stay at this 3-star aparthotel in Montauk. Enjoy free Wi-Fi, free parking and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...
8.4/10 Very Good! (414 reviews)
"Property was clean and nice but did not smell good inside, it need candles and air freshener, also think something was off about the sewage system"

Reviewed on 16 Sept 2025

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.

Popular places to visit

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Shelter Island Whale's Tail

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

Wades Beach

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.

Wades Beach

Shell Beach

Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

฿4,716
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

฿4,429
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM

฿10,802
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: PM
See all activities in Shelter Island

Cities near Shelter Island

East Hampton Main Beach

East Hampton