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.
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.
You might want to play some rounds at Gardiner's Bay Country Club, located 1.8 mi (2.9 km) from central Shelter Island. If Gardiner's Bay Country Club doesn't quite scratch your golfing itch, Shelter Island Country Club, and Island's End Golf and Country Club are also nearby.
Mashomack Preserve is 1.3 mi (2.1 km) from central Shelter Island, why not stop by during your stay. Want to stretch your legs some more? Head to Cedar Point County Park and Foster Memorial Town Beach, both nearby.
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.
Hop aboard a ferry to this tranquil island retreat, where pristine beaches and lush nature preserves await. Unwind at Sunset Beach, explore the Mashomack Preserve, or delve into local history at the Shelter Island Historical Society.
"The property was beautiful! The view was beautiful! Staff was very helpful and friendly. The only thing that would make it better would be some sort of convenience shop for forgotten essentials. For example medications.. toiletries etc.. my son ate something that disagreed with him and we could not get him a simple Tums to make him feel better. A hotel of this size normally has at least a small area to purchase these items. "
"My fiancé and I recently spent a few nights at this beautiful hotel by the water in Old Saybrook, and we couldn’t have asked for a more perfect getaway. From start to finish, everything was exceptional.
The cleanliness throughout the property was flawless — every space felt fresh, spotless, and well cared for. It set the tone for a relaxing and worry-free stay.
The amenities were fantastic. We especially enjoyed the spa and the cozy common areas where we could unwind together. Everything was thoughtfully designed to create a luxurious and peaceful atmosphere.
The dining experience was another highlight. Every meal we had was delicious, with fresh ingredients, creative menus, and warm, attentive service. Whether it was breakfast with a view or a romantic dinner by candlelight, the setting made it all feel extra special.
What truly made the experience unforgettable was the view. Being right on the water, we were treated to stunning sunrises and serene evenings. Sitting together on the balcony, watching the sunset over the water, was one of the most peaceful and memorable parts of our trip.
This hotel offered the perfect mix of romance, comfort, and beauty. My fiancé and I left feeling refreshed, connected, and already dreaming of our next visit. Highly recommended for couples looking for a scenic and serene escape."
"Having difficulties walking, the owner came to my car and helped bring my bags into my room. He owns an Indian restaurant next door. The food is superb. "
"We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due to its being vintage, if I’m spending $800 a night I want a modern, spacious bathroom. "
How much does a hotel room cost in Shelter Island?
You can find top hotels in Shelter Island from $205 with options to suit your budget and needs. If you're after an affordable hotel in Shelter Island that meets all of your requirements, set your filters and then sort the results by "Price: low to high". If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Shelter Island hotels?
Members can save up to 20% on select hotels in Shelter Island. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.
Can I book Shelter Island hotels with free cancellation?
In order to book a refundable Shelter Island hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some popular hotels in central Shelter Island?
For hotels in central Shelter Island, check out The Harbor Front Inn and Sag Harbor Inn. Travelers love The Harbor Front Inn for its location, as well as the seasonal outdoor pool, free continental breakfast and 24-hour health club this hotel offers. Sag Harbor Inn is another popular central hotel with an outdoor pool, a free continental breakfast and free parking. Pipes Cove and The Heights are some of the most central neighborhoods for your Shelter Island vacation.
Are all taxes and fees included in the Shelter Island hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
What accommodations do travelers recommend in Shelter Island?
If you're looking for the flexibility to change your travel plans to Shelter Island, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Shelter Island if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 85 vacation homes. You can also consider one of the 5 cottages for your trip.
What will the weather in Shelter Island be like during my trip?
The warmest months in Shelter Island are usually August and July with an average temp of 70°F. January and February are the chilliest months when the average temp is 38°F. The rainiest months are October and December.
Why should I book my Shelter Island accommodation with Hotels.com?
There are plenty of reasons to book your Shelter Island travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.
Find out more about Shelter Island
Find out more about Shelter Island
If you're looking for a place to get away, look no further than Shelter Island. Whether you're planning to stay for a night or for the week, the area around Shelter Island has accommodations to fit every need. Search for hotels in Shelter Island with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Shelter Island hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Shelter Island hotel deals are here with our lowest price guarantee.
Shelter Island Travel Information
Best Time to Visit
May, June and July
Average Stay
2 days
International Airports
John F. Kennedy Intl. Airport (JFK), Liberty Intl. Airport (EWR)
Popular Sights
Wolffer Estates Vineyard, Orient Point County Park and 67 Steps Beach
