Luxury Hotels & Resorts in Shelter Island from AU$111

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Check availability on Shelter Island Luxury Hotels

Our top choices for Shelter Island luxury hotels

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (511 reviews)
  • cleanliness
    Riverside luxury awaits at this 4-star Ivoryton hotel with massages, gardens, and gourmet dining.
"Our getaway to the Copper Beech Inn was superb! There is such an ambiance of elegance, beauty, joy and care. Everything is immaculate and the floral gardens are truly beautiful. The staff appears to truly enjoy their work and they put forth their best effort to make certain guests are enjoying their stay. So appreciate the serenity experienced. "
United States
Ken
The price is AU$449
includes taxes & fees
18 May - 19 May
Copper Beech Inn

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very good, (781 reviews)
"It was the perfect space for relaxation after a busy week."
United States
Katie
The price is AU$1,055
includes taxes & fees
26 May - 27 May
Gurney's Montauk Resort & Seawater Spa

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (85 reviews)
"Beautiful resort with historic charm, very well positioned on a scenic cove. Upgraded luxury with a classic yacht club tone that is both beautiful and comfortable yet approachable and relaxing. Service is excellent and there to support your needs everyone is attentive. Plenty of amenities to enjoy but all set to a relaxing tone. "
United States
John
The price is AU$594
includes taxes & fees
28 May - 29 May
The Pridwin Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (369 reviews)
  • cleanliness
    Madison beachfront hotel offers private shoreline, spa treatments, and upscale dining for coastal luxury.
"the spa calm and inviting"
United States
Per
The price is AU$526
includes taxes & fees
25 May - 26 May
Madison Beach Hotel

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (165 reviews)
"Lovely historic property, very comfortable beds and linen and fresh buffet breakfast. Staff very attentive and friendly, excellent on site restaurant."
United Kingdom
Liz
The price is AU$1,264
includes taxes & fees
28 May - 29 May
The 1770 House Restaurant & Inn

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (94 reviews)
  • cleanliness
    Indulge in beach-side luxury at this renovated colonial hotel offering spa services and Frette linens.
"We just spent two nights at round tree and it was an absolutely incredible experience from start to finish. The staff is so wonderful, attentive, and kind and truly made us feel welcomed and special. We were celebrating our ten year anniversary and upon checking in they provided us with an upgrade and a complimentary bottle of champagne. The room and the whole place felt luxurious, modern, and special without being too uppity which many places in the Hamptons can be. And the complimentary...
United States
Jillian
The price is AU$1,668
includes taxes & fees
1 June - 2 June
The Roundtree, Amagansett

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Montauk retreat offers beachfront elegance with private shoreline, marina access, and luxurious spa services.
"really recommended! Lake view was wonderful!"
United States
GERTA
The price is AU$554
includes taxes & fees
20 May - 21 May
Montauk Yacht Club

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (151 reviews)
  • cleanliness
    Hamptons elegance thrives at this luxury retreat offering a full-service spa, outdoor pool, and rooftop terrace in charming Bridgehampton.
"Overall it was a great stay! Best part of the cottage was the bathroom with its deep big tub and walk in shower. But the room itself lacked visual appeal & some conveniences usually associated with booking a cottage which is more private and removed from the house. Could use more and better art in the room. I would also trade all the storage space for a mini fridge, tea kettle or coffee maker. Also the only full-size mirror is hidden far back in the bathroom which isn’t terrible but very...
United States
Au Chau Mimi
The price is AU$1,278
includes taxes & fees
4 June - 5 June
Topping Rose House

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (152 reviews)
"Beachfront paradise with stylish rooms, dreamy views, and thoughtful touches."
United States
Jacquelyn
The price is AU$587
includes taxes & fees
19 May - 20 May
Silver Sands Motel & Beach Bungalows

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (84 reviews)
  • cleanliness
    Indulge in fireplaces and premium bedding at this colonial bed & breakfast near the beach.
"The breakfast is amazing, beds super comfortable and grounds stunning. Location was perfect and staff wonderful. Also the tub in our room was incredible. Only suggestion would be for coffee in the room in the morning. Otherwise it was a literal perfect stay "
United States
Jessica
The price is AU$791
includes taxes & fees
21 May - 22 May
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 Crescent Beach, 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, Crescent Beach and Gardiner's Bay Country Club. If you have some spare time during your trip, you might want to check out Mashomack Preserve and Shell Beach.

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