Luxury Hotels & Resorts in Shelter Island from AU$166

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Check availability on Shelter Island Luxury Hotels

Our top choices for Shelter Island luxury hotels

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (607 reviews)
"Nice place"
United States
Mateusz
The price is AU$271
includes taxes & fees
21 Jan - 22 Jan
Sound View Greenport

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (162 reviews)
"Amazing stay"
United States
Liana
The price is AU$346
includes taxes & fees
25 Jan - 26 Jan
Journey East Hampton

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (144 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, (343 reviews)
"Wonderful staff"
United States
Rebecca
The price is AU$420
includes taxes & fees
5 Feb - 6 Feb
Madison Beach Hotel

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (60 reviews)
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (150 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is AU$263
includes taxes & fees
21 Jan - 22 Jan
The Maidstone

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (719 reviews)
"Very nice place and atmosphere will definitely be there again "
United States
NASHAT
The price is AU$516
includes taxes & fees
9 Feb - 10 Feb
Gurney's Montauk Resort & Seawater Spa

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (92 reviews)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is AU$1,063
includes taxes & fees
21 Jan - 22 Jan
The Roundtree, Amagansett

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (140 reviews)
"Our second home :)"
United States
olivia
The price is AU$826
includes taxes & fees
23 Jan - 24 Jan
Topping Rose House

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (77 reviews)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is AU$468
includes taxes & fees
25 Jan - 26 Jan
Mill House Inn
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.

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 Mashomack Preserve. If you have some spare time during your trip, you might want to check out Crescent Beach and Gardiner's Bay Country Club.

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