Where to stay in Shelter Island

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 Crescent Beach and Sunset Beach.

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 Crescent Beach.

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.

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.

Shorewood

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

Montclair Colony

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

The Atlantic Hotel

1655 County Road 39, Southampton, NY

CA $223

CA $290 total

Sep 21 - Sep 22

includes taxes & fees

Book a stay at this business-friendly hotel in Southampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

7/10 Good! (915 reviews)

"Nice staff and the hotel is fine."

Reviewed on Aug. 24, 2025

Quality Inn Old Saybrook - Westbrook

100 Essex Rd, Old Saybrook, CT

CA $139

CA $160 total

Sep 25 - Sep 26

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! (1,007 reviews)

"The salt water pool was awesome! Would have liked it a little bit warmer. Breakfast was great, eggs, sausage, English muffins, bagels coffee,tea, waffles, fruit, cereal, juice! Rooms were spacious with fridge. Would highly recommend"

Reviewed on Aug. 24, 2025

Marram

21 Oceanview Terrace, Montauk, NY

CA $391

CA $708 total

Sep 18 - Sep 19

includes taxes & fees

Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point and South Edison Beach are ...

8.6/10 Excellent! (216 reviews)

"Small, but comfortable room. Excellent location right on the beach. There was a mix up with our dinner at the hotel one night and my husband’s dinner came out much later than mine. It wasn’t a big deal, but the hotel comped our meal, brought us a free dessert, and comped our post-dinner drinks at ..."

Reviewed on Aug. 19, 2025

See all 4,711 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.

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

Shelter Island

Stay at this vacation home in Shelter Island. Enjoy air conditioning. Popular attractions Wades Beach and Shelter Island Historical Society are located ...

Waterfront House With Dock And Private Beach

Shelter Island

Stay at this vacation home in Shelter Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mashomack Preserve and Wades Beach are located ...

10/10 Exceptional! (14 reviews)

"Beautiful house. We loved the location and the view was amazing. We loved using the kayak and just relaxing here."

Reviewed on Aug. 13, 2025

Montauk Manor

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! (1,242 reviews)

"very nice and organized"

Reviewed on Aug. 24, 2025

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.

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.

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.

Wades Beach

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

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.

Shelter Island Historical Society

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

Things to do

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $191

per adult

See all activities in Shelter Island

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Shelter Island

Travel Guide

Visit Shelter Island

Where to stay in Shelter Island

Silver Beach

Menantic Creek

Coecles Harbor

Hay Beach

Shorewood

Montclair Colony

The Atlantic Hotel

Quality Inn Old Saybrook - Westbrook

Marram

4-bedroom house on lake in delightful Shelter Island with WiFi, AC on 3.2 acres

Waterfront House With Dock And Private Beach

Montauk Manor

Check Shelter Island hotel availability

Popular places to visit

Gardiner's Bay Country Club

Shelter Island Whale's Tail

Mashomack Preserve

Wades Beach

Shell Beach

Shelter Island Historical Society

Things to do

From Mattituck: North Fork Area Bike Tour with Food Tasting

Cities near Shelter Island

East Hampton

Sag Harbor

East Marion

Greenport West