Name: Montauk Yacht Club
Price range: CA $1,007

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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 Wades Beach.

A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Wades Beach and Shelter Island Historical Society.

A pebble beach with calm water, a distant bridge, and a forested island.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

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.

An aerial view of a large estate surrounded by water, featuring a prominent mansion, rocky shorelines, and a small island with a lighthouse.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Wades Beach and Mashomack Preserve.

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

CA $146

CA $167 total

Aug 4 - Aug 5

includes taxes & 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. ...

8/10 Very good! (1,005 reviews)

"The room was nice and very well renovated, HOWEVER the floor was so dirty that it left out socks black after walking around the room. The bed was clean and the location was good but the cleanliness of the room in general left something to be desired."

Reviewed on Jul 31, 2026

Sound View Greenport

58775 County Rd 48 Greenport NY

Book a stay at this beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...

8.4/10 Very good! (672 reviews)

"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went ..."

Reviewed on Jul 29, 2026

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Montauk Yacht Club

32 Star Island Rd Montauk NY

CA $1,007

CA $1,310 total

Aug 31 - Sep 1

includes taxes & fees

Book a stay at this luxury hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...

See all 4,741 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.

Bright and Spacious Summer Home Steps from the Beach

Shelter Island NY

Book a stay at this family-friendly vacation home in Shelter Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Gardiner's Bay Country ...

9/10 Wonderful! (42 reviews)

"Perfect location, family friendly and easy communication with host!"

Reviewed on Jul 8, 2026

Montauk Manor

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 ...

9.2/10 Wonderful! (1,372 reviews)

"The suite fit our needs perfectly. Was great to come back from beach and go to the pool to rinse off. Sunsets were fabulous, great view!"

Reviewed on Jul 29, 2026

North Fork Resort

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' ...

9.4/10 Exceptional! (41 reviews)

"Very nice units. Pool area and outdoor space around pool also very nice. Also excellent location and Greenport is a fantastic town Lot of work still being done on the property. Once completed the place will be great."

Reviewed on Jul 29, 2026

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.