Luxury Hotels & Resorts in Shelter Island from AU$107

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Our top choices for Shelter Island luxury hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (736 reviews)
"Room was spotless, staff were great and the resort is top notch!!"
United States
Carrie
The price is AU$673
includes taxes & fees
8 Mar - 9 Mar
Gurney's Montauk Resort & Seawater Spa

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162 reviews)
"Wonderful Inn & staff…The restaurant is also excellent! "
United States
Anthony
The price is AU$518
includes taxes & fees
8 Mar - 9 Mar
The 1770 House Restaurant & Inn

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (81 reviews)
"Great place to stay. Very walkable, lovely room and comfortable bed. "
Australia
Alex
The price is AU$448
includes taxes & fees
8 Mar - 9 Mar
Mill House Inn

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is AU$474
includes taxes & fees
6 Apr - 7 Apr
James Pharmacy Bed & Breakfast

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (164 reviews)
"Amazing stay"
United States
Liana
The price is AU$312
includes taxes & fees
8 Mar - 9 Mar
Journey East Hampton

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (145 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (346 reviews)
"Staff and hotel are lovely "
United States
Steven
The price is AU$362
includes taxes & fees
31 Mar - 1 Apr
Madison Beach Hotel

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (508 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is AU$454
includes taxes & fees
6 Apr - 7 Apr
Copper Beech Inn

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (93 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is AU$1,017
includes taxes & fees
8 Mar - 9 Mar
The Roundtree, Amagansett

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (143 reviews)
"Our second home :)"
United States
olivia
The price is AU$799
includes taxes & fees
10 Mar - 11 Mar
Topping Rose House
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.

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Top Shelter Island Hotel Reviews

Frequently asked questions

Are you looking for a luxury hotel for your Shelter Island holiday?
Use Expedia to help you arrange a flight to East Hampton, NY (HTO) airport or Fishers Island, NY (FID-Elizabeth Field) airport, and then choose from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you want to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Shelter Island offers. Shelter Island has some interesting things to see and do including Sunset Beach and Shelter Island Whale's Tail, so you might want to take in the local sights during your visit.
When can I expect good weather in Shelter Island?
Planning for the weather is a good way to make your trip to Shelter Island relaxing and enjoyable, especially when you're splurging. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.
What's there to see and do in Shelter Island?
Take in some sights and attractions while you're in Shelter Island by visiting Sunset Beach, Shelter Island Whale's Tail and Wades Beach. If you have some spare time during your trip, you might want to check out Mashomack Preserve and Crescent Beach.

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