Shelter Island

Travel Guide

Photo by tom owens
Photo by Rich Barton

Where to stay in Shelter Island

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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 Sunset Beach and Crescent Beach.

Silver Beach
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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 Mashomack Preserve.

Menantic Creek
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Coecles Harbor

While Coecles Harbor isn't home to many top sights, Gardiner's Bay Country Club and Sunset Beach 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 Mashomack Preserve and Sunset Beach.

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 Sunset Beach and Mashomack Preserve.

Montclair Colony
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 HK$1,994 per night from 19 Jan to 20 Jan
HK$1,994
HK$2,733 total
19 Jan - 20 Jan
includes taxes & fees
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 Hills ...
8.2/10 Very Good! (707 reviews)
Excellent

Reviewed on 31 Dec 2025

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
Fully refundableReserve now, pay when you stay
The price is HK$1,783 per night from 15 Jan to 16 Jan
HK$1,783
HK$2,185 total
15 Jan - 16 Jan
includes taxes & fees
Stay at this beach resort in Westbrook. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (1,005 reviews)
Great place!

Reviewed on 31 Dec 2025

Water's Edge Resort & Spa
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
Stay at this beach hotel in Montauk. Enjoy free Wi-Fi, a beach locale and parking (surcharge). Popular attractions South Edison Beach and Kirk Park Beach are ...
9.2/10 Wonderful! (187 reviews)
I always have a 5/5 stay at Montauk Blue.

Reviewed on 19 Nov 2025

Montauk Blue Hotel
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 Wi-Fi, an outdoor pool and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,276 reviews)
We gave stayed at Montauk Manor for the holiday for many years. The lobby area is grand and very festive during the holidays. The units are clean and comfortable with amenities that make it easy to eat in if desired. The front desk staff are helpful and friendly and the in house restaurant, Montes, ...

Reviewed on 30 Dec 2025

Montauk Manor
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor NY
Stay at this family-friendly holiday home in Sagaponack. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. ...
10/10 Exceptional! (87 reviews)
Property was very responsible and amazing to work with!!

Reviewed on 29 Sept 2025

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Escape to Sag Harbor

Escape to Sag Harbor

Sag Harbor NY
Stay at this holiday home in Sag Harbor. Enjoy private pools, a fitness centre and a garden. Popular attractions Foster Memorial Town Beach and Sag Harbor Whaling ...
10/10 Exceptional! (55 reviews)
We had a wonderful stay at this beautiful house in the Sag Harbor with our adult children and my husband.The pool and pool table were such a high light and the house was fully stocked with everything we needed.Dayle was fantastic with communication and made everything so easy. We were in town for ...

Reviewed on 30 Sept 2025

Escape to Sag Harbor
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

Things to do