A wooden gazebo by a pond with a large tree trunk nearby.

Luxury Hotels & Resorts in Shelter Island from AU$271

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Check availability on Shelter Island Luxury Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Shelter Island luxury hotels

A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.
A grassy area with trees and a view of a body of water.

1. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
AU$459
includes taxes & fees
21 Oct - 22 Oct
Silver Sands Motel & Beach Bungalows
A spacious room with wicker furniture, large windows, and a view of the sea.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with a deck extending over the water, featuring large windows and a dining area.

2. Sound View Greenport

Sound View Greenport
Greenport
AU$418
includes taxes & fees
25 Oct - 26 Oct
Sound View Greenport
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.

3. Oyster Estate

Oyster Estate
Greenport
AU$566
includes taxes & fees
5 Oct - 6 Oct
Oyster Estate
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A spacious living room with a fireplace, comfortable seating, and large windows.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

4. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Immerse in beachside elegance at this Sag Harbour retreat offering luxurious spa services, seasonal pool, and upscale dining.
AU$747
includes taxes & fees
5 Oct - 6 Oct
Faraway Sag Harbor
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

5. Journey East Hampton

Journey East Hampton
East Hampton North
AU$448
includes taxes & fees
18 Oct - 19 Oct
Journey East Hampton
A two-story building with a porch and a flagpole.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
A hotel interior with a long corridor, seating areas, and a reception desk.

6. The Maidstone

The Maidstone
East Hampton
AU$466
includes taxes & fees
25 Oct - 26 Oct
The Maidstone
An outdoor dining area with trees and tables under string lights.
A white house with a sign reading "The 1770 House Restaurant & Inn."
A living room with a fireplace, a television mounted above it, and a dining area in the background.
A restaurant with wooden beams, tables with white tablecloths, and a bar area.

7. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
AU$882
includes taxes & fees
19 Oct - 20 Oct
The 1770 House Restaurant & Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.
A large, modern house with a swimming pool, surrounded by lush greenery and trees.
A residential area with houses, a wooden deck, and a garden with pink flowers.
A sliding glass door leading to an outdoor deck with a view of a swimming pool and greenery.

8. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
Clearwater Beach
AU$1,100
includes taxes & fees
6 Oct - 7 Oct
East Hampton Art House Bed & Breakfast
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.
A large, two-story house with a wrap-around porch and a conservatory.
A bar area with a long counter, multiple stools, and a well-stocked bar.

9. Copper Beech Inn

Copper Beech Inn
Ivoryton
  • Riverside luxury awaits at this 4-star Ivoryton hotel with massages, gardens, and gourmet dining.
AU$451
includes taxes & fees
28 Sept - 29 Sept
Copper Beech Inn
A wooden pathway leading to a beach with a view of the ocean.
An indoor swimming pool with a view of the beach, lounge chairs, and large windows.
A modern living room with a sofa, a chair, a coffee table, and a view of the sea.
A house with a stone wall and a garden with various plants and flowers.

10. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
AU$752
includes taxes & fees
29 Sept - 30 Sept
Gurney's Montauk Resort & Seawater Spa
View all properties

Top Shelter Island Hotel Reviews

Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"I really love this hotel! The rooms are beautiful, the service is excellent, and I’ve had a great experience every time I’ve stayed there. I’ve been a few times already and will definitely be coming back next year!"
Veronika 2-night trip
Posted 1 day ago
Montauk Yacht Club
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"Closest to beach and town"
john 1-night trip
Posted 3 days ago
Ocean Resort Inn

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 Historical Society, 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 Historical Society 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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