Are there any 5-star vacation rentals in Shelter Island?

There are no 5-star vacation rentals in Shelter Island on our site, but there are some other highly rated options worth checking out. Search through our vacation rentals in Shelter Island to find the perfect place for your getaway.

Find 5 Star Hotels in Shelter Island, NY from $271

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Compare Shelter Island 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Mill House Inn

Pantigo Road Historic District

"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...

margaret

$330 nightly

Dec 8 - Dec 9

Total with taxes and fees

Casa Newmark Holiday home 7 BestStayz.1

Sagaponack

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Shelter Island.

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

$439 nightly

$502 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

8.2/10 Very Good! (695 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

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Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Ready for an incredible adventure? Add further enjoyment on your next trip to Shelter Island by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Shelter Island so popular in the last year. There's no reason to delay a getaway to Shelter Island any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Shelter Island are the perfect places to relax in during your next getaway. You deserve the great vacation you're dreaming about.

Get a Great Deal on 5-Star Hotels in Shelter Island

You'll have a fantastic time at one of these 5-star hotels. Spa treatments, delicious meals, and attentive guest service are all waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A rejuvenating facial treatment to help your cares fall away? A concierge to help you suggest the next attraction to visit? Plush carpeting, lip-smacking main courses, and even spectacular views...these hotels will leave you amazed. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

You won't sleep and order room service the entire time, though. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Shelter Island are the perfect place to relax after an exciting day.

Make Your Escape

The results are in, and Shelter Island 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Opt for one of Expedia's Shelter Island 5-star hotels today and soothe yourself in luxe surroundings tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Shelter Island?

How much you pay for a 5-star hotel in Shelter Island depends on things like when you want to go and the length of your break. An insider tip for scoring an awesome deal? Use our pricing filters to check out the available options for your preferred dates.

Search for the lowest price per night from $271

What makes a hotel 5 stars in Shelter Island?

In Shelter Island, a hotel must offer a certain amount of high-end conveniences to be designated 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury toiletries and more. What also sets 5-star hotels apart is their guest-focused standard of service. You can expect things like in-room massages, nightly turn-down services and concierge services. Some may even offer special touches such as welcome gifts.

Are there any 5-star all-inclusive resorts in Shelter Island?

Our handy filters are the quickest way to search for exactly what you want. Check the "All inclusive" and "5-star" boxes to see the most upscale properties in Shelter Island where your accommodations, meals, entertainment and activities are included in the price. At these stays, your trip is pure leisure from the moment you arrive.

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