Shelter Island

Travel Guide

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

Where to stay in Shelter Island

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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
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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
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Coecles Harbor

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

Coecles Harbor
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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
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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 Shell Beach and Mashomack Preserve.

Shorewood
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Montclair Colony

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

Montclair Colony
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is S$163 per night from 3 Aug to 4 Aug
S$163
3 Aug - 4 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,002 reviews)
"Great location and pool, close to a wonderful restaurant"

Reviewed on 30 Jun, 2025

Quality Inn Old Saybrook - Westbrook
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is S$642 per night from 10 Jul to 11 Jul
S$642
10 Jul - 11 Jul
includes taxes & fees
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Montauk Point Lighthouse and Montauk ...
9.2/10 Wonderful! (93 reviews)
"Highly recommended"

Reviewed on 7 Jul, 2025

Montauk Blue Hotel
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
8.4/10 Very Good! (1,002 reviews)
"5 stars only thing is the pool closed early. It was very expensive for everything. Breakfast was not included and was overpriced for everything. We even had to rent tennis racquets for the courts."

Reviewed on 6 Jul, 2025

Get rates
Montauk Yacht Club
See all 4,796 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 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,208 reviews)
"Beautiful property and spacious rooms"

Reviewed on 7 Jul, 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 WiFi, free parking, and a beach locale. Popular attractions Montauk Point Lighthouse and Montauk Point ...
8.4/10 Very Good! (388 reviews)
"good location, short walk to beach. modern room.. walk to town 3 short blocks"

Reviewed on 30 Jun, 2025

Montauk Oceanside Suites
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 WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (288 reviews)
Decent and Better priced
"A good choice for “affordable” stays in the Hamptons. The place is not “fresh” or chic by any means but it’s very acceptable and half the price of many other accommodations. Over all it’s a good value. Clean, well located and homey."

Reviewed on 28 Jun, 2025

Windward Shores Ocean Resort
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

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

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 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

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

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

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

S$203
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Half Day Private Long Island Wine Tour Experience

Half-Day Private Long Island Wine Tour Experience

S$371
per adult
Half-Day Private Long Island Wine Tour Experience
Vetted Flights and food pairings at local winery.

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

S$433
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
See all activities in Shelter Island
East Hampton Main Beach

East Hampton

Southold

Southold