Lodging Image

Find 5 Star Hotels in Shelter Island, NY from ￥75,606

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island 5 Star Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Shelter Island 5-star hotels

Front of property - evening/night

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (88 reviews)
"Couldn't have been nicer. Dawn and Tiffany were grcious and accomodating."
Canada
Ronald
The price is ￥162,911
￥235,448 total
includes taxes & fees
Aug 18 - Aug 19
Mill House Inn
House | Outdoor spa tub

Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1
5.0 star property
Sagaponack
Casa Newmark Holiday home 7 BestStayz.1
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.
Montauk Yacht Club

Montauk Yacht Club

32 Star Island Rd Montauk NY
The price is ￥112,810 per night from Jul 30 to Jul 31
￥112,810
￥147,572 total
Jul 30 - Jul 31
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Still don't see what you're looking for?
See all properties in Shelter Island.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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.

See all hotels in Shelter Island
A wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

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 factors such as when you plan to travel and the length of your break. Our top tip for landing an awesome deal? Use our pricing filters to compare the available hotels for your selected dates.

  • Search for the lowest price per night from ￥75,606

What makes a hotel 5 stars in Shelter Island?
From fine dining restaurants and fitness centers to pools and superior bedding, the 5-star experience in Shelter Island is all about luxury and relaxation. But it requires more than just upscale conveniences to get a 5-star rating. Hotels must also offer outstanding guest-centric services like in-room massage treatments, on-site laundry and a nightly turn-down service.
Are there any 5-star all-inclusive resorts in Shelter Island?
Find a luxury escape that includes your lodging, meals, drinks and entertainment in Shelter Island with Expedia's filters. Search for properties with a 5-star rating and select the "All inclusive" filter. Have a look at what's included in the price. That way, you're ready to take advantage of the premium perks on offer from the moment you get there.