Shelter Island, NY

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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Silver Beach

While Silver Beach might 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 Shell Beach.

Silver Beach
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Coecles Harbor

When in Coecles Harbor, you can plan a visit to Mashomack Preserve and Sunset Beach, some noteworthy sights in the nearby area.

Coecles Harbor
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Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Mashomack Preserve.

Menantic Creek
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Montclair Colony

While Montclair Colony isn't home to many top sights, Shell Beach and Sunset Beach are some notable places to visit nearby.

Montclair Colony
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Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Shorewood
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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.

Hay Beach
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is SAR 285 per night from Dec 12 to Dec 13
SAR 285
SAR 321 total
includes taxes & fees
12 Dec - 13 Dec
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 ...
7.4/10 Good! (1,002 reviews)
"My mattress was less than good and needs to be replaced. Otherwise, the facility was clean and reasonable with a good breakfast."

Reviewed on 26 November 2024

Quality Inn Old Saybrook - Westbrook
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 SAR 259 per night from Dec 1 to Dec 2
SAR 259
SAR 298 total
includes taxes & fees
1 Dec - 2 Dec
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. ...
7.6/10 Good! (892 reviews)
"Everything was satisfactory"

Reviewed on 15 November 2024

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 SAR 946 per night from Dec 2 to Dec 3
SAR 946
SAR 1,284 total
includes taxes & fees
2 Dec - 3 Dec
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 our reviews. ...
8.2/10 Very Good! (608 reviews)
"Beautiful views. Great staff and amenities."

Reviewed on 28 November 2024

Gurney's Montauk Resort & Seawater Spa
See all 4,675 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! (1,073 reviews)
"Can’t wait to visit again!"

Reviewed on 24 November 2024

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 daily housekeeping. Popular attractions South Edison Beach and Kirk Park Beach ...
8.4/10 Very Good! (340 reviews)
"This property is perfect especially off-season as it is very close to town, gives you room in the unit, is across the street from the beach, and is very quiet and affordable. There is a kitchen so you can cook if you want to and they give you a coffee maker to use but no coffee like a hotel does. ..."

Reviewed on 25 November 2024

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! (262 reviews)
while at the Hamptons....!!!!
"smooth check in, very clean place, via text comunication extremely effective, we also loved the small kitchen in the room, ideal for some coffee making or warming ubp a bite we simply loved the place."

Reviewed on 17 November 2024

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

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

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 Historical Society

4/5(1 review)

You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

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

Shell Beach

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

Shell Beach

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House