2025 Shelter Island, New York Hotels

Up To 10% Off Select Hotels With AARP Member Discounts

Photo by tom owens

Choose from AARP Discount Shelter Island Hotels with Free Cancellation

Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
33.98 km from city center
Get rates
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 ...
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
32.71 km from city center
Get rates
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 ...
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
29.68 km from city center
Get rates
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. ...
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Free Cancellation
Reserve now, pay when you stay
25.1 km from city center
Get rates
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
8.14 km from city center
Get rates
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
33.29 km from city center
Get rates
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Free Cancellation
Reserve now, pay when you stay
31.4 km from city center
Get rates
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
24.93 km from city center
Get rates
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. ...
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street, Sag Harbor, NY
8.13 km from city center
Get rates
Stay at this 3.5-star business-friendly hotel in Sag Harbor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd, Southampton, NY
Free Cancellation
Reserve now, pay when you stay
22.07 km from city center
Get rates
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St, Greenport, NY
4.2 km from city center
Get rates
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Free Cancellation
Reserve now, pay when you stay
23.94 km from city center
Get rates
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
27.92 km from city center
Get rates
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 ...
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
21.51 km from city center
Get rates
Stay at this hotel in Southampton. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Kenny's Tipperary Inn

Kenny's Tipperary Inn

2 out of 5
432 West Lake Drive, Montauk, NY
33.3 km from city center
Get rates
Stay at this motel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
5.79 km from city center
Get rates
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Don't see what you're looking for?
See all available properties in Shelter Island
View all properties
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.

Shelter Island Hotels

Are you staying in Shelter Island for a well-deserved break, or are you wanting to show your grandchildren the attractions? AARP® Travel Center Powered by Expedia® can assist you in getting the exact hotel you want for an outstanding value. There are several accommodation options for you and your family to choose from. You can use your membership benefits to book a hotel that is near the sights you want to see, or an exclusive resort that pulls out all the stops. There are plenty of things to see and do in Shelter Island, and as a valued member you will save a ton on your vacation.

Book A Great Shelter Island Hotel

There are 4,743 accommodations to choose from in Shelter Island, with reviews to check out so you and your vacation crew will know what to expect at each possible accommodation. Once you get settled in your Shelter Island hotel room, you can investigate all this city has to offer. You can ask your hotel's front desk or click on our "Things To Do" tab if you are unsure where start off your vacation in Shelter Island. If there are something else you're really looking forward to in Shelter Island, we can help you find them. Wherever your vacation takes you, you will spend more time making the most of your trip when booking with AARP Travel Center Powered by Expedia.

Book Your Accommodations with the AARP Travel Center Today

We are going to ensure you get the best deals around when you book your next Shelter Island vacation. When you are ready to see Shelter Island's attractions, like an and , we'll help you get everything booked for you and your grand kids. And thanks to our discounted travel rates, you do not have to think about breaking the bank in order to have your ideal trip. With AARP, you'll look forward to planning your next vacation. You can feel good in knowing that you have scored the very best deal. Book with AARP, and both you and your wallet will be happy about your travels.