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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Shelter Island 4-star hotels

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 beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.
A modern living room with a sofa, a chair, a coffee table, and a view of the sea.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$12,902
NT$17,688 total
includes taxes & fees
Nov 1 - Nov 2
Gurney's Montauk Resort & Seawater Spa
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$7,334
NT$9,289 total
includes taxes & fees
Nov 1 - Nov 2
Sound View Greenport
A modern outdoor deck with lounge chairs and a view of the beach.
A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.
A room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.
A modern hotel with multiple balconies and large windows.

3. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$5,849
NT$8,502 total
includes taxes & fees
Nov 1 - Nov 2
Offshore Montauk
A spacious bar area with a marble countertop, multiple bar stools, and a view of the marina through large windows.
A deck with wicker chairs and a table, overlooking a beach with umbrellas and lounge chairs.
A marina with boats docked, a grassy area with a tent, and houses in the background.
A beach with two sun loungers, a beach umbrella, and a basket.

4. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Sophie
NT$6,581
NT$11,155 total
includes taxes & fees
Oct 27 - Oct 28
Montauk Yacht Club
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
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.

5. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$13,332
NT$16,755 total
includes taxes & fees
Nov 1 - Nov 2
Faraway Sag Harbor
A beachside patio with lounge chairs, umbrellas, and a wooden building with a balcony overlooking the ocean.
A room with a large window overlooking a beach, a framed abstract artwork, and a lamp on a table.
A wooden building with a beach view, a wooden deck, and a sandy path leading to the beach.
A poolside area with lounge chairs and orange umbrellas, overlooking the ocean.

6. Marram

Marram
Montauk
United States
NATAVAN
NT$7,357
NT$11,681 total
includes taxes & fees
Oct 15 - Oct 16
Marram
A hotel room with a sofa, a coffee table, a TV, and a framed picture on the wall.
A room with a round table, two white chairs, a potted plant, and a window with curtains.
A bedroom with a bed, bedside lamp, window with view, and a hanging tapestry.
A kitchen with a sink, a coffee maker, a vase with flowers, and a framed picture on the wall.

7. Hotel Corduroy

Hotel Corduroy
Culloden Shores
United States
Heather
NT$6,214
NT$7,739 total
includes taxes & fees
Nov 1 - Nov 2
Hotel Corduroy
Outdoor spa tub
A grassy area with trees and a view of a body of water.
A room with a bed, two wicker chairs with checkered cushions, a small round table with a vase of flowers, and a view of a lake through a window with a bamboo blind.
A neatly arranged bedroom with a bed, a bedside table with a telephone, and a wall-mounted light.

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
NT$10,353
NT$11,829 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A living room with a fireplace, two sofas, a coffee table, and a chair.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.

9. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$7,988
NT$10,039 total
includes taxes & fees
Oct 12 - Oct 13
Journey East Hampton
A spacious bedroom with a large bed, a sitting area with a sofa, a chair, and a small ottoman. There are two windows with curtains, a fireplace, and a flat-screen TV mounted on the wall.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
A room with a wicker sofa, a large potted plant, and a window with blinds.
A kitchen with a central island, two wicker chairs, and a bar area with glasses.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,713
NT$10,452 total
includes taxes & fees
Oct 19 - Oct 20
The Maidstone
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
A dining area with a round table, chairs, a vase, and a painting on the wall.

11. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
NT$8,283
NT$10,436 total
includes taxes & fees
Nov 1 - Nov 2
Oyster Estate
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
A person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.
A breakfast buffet with various food items and beverages.
A cozy room with a large window, a sofa, a small table with a tray, and a pair of slippers on the floor.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
NT$15,132
NT$18,325 total
includes taxes & fees
Oct 5 - Oct 6
Canoe Place Inn and Cottages
A bedroom with two beds, a wooden rocking chair, a small table, and a view of the outdoors.
A beach with white umbrellas arranged in a line.
A spacious living room with a high ceiling, wooden beams, a large sofa, a coffee table, and a dining area with stools.
A two-story building with a pool, outdoor seating, and potted plants.

13. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$7,008
NT$9,790 total
includes taxes & fees
Oct 19 - Oct 20
Hero Beach Club
A multi-story hotel with balconies and a beach view.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.
A coastal hotel with a pier, beach, and boats.
A grand staircase with a chandelier, a reception desk, and a fireplace.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$9,042
NT$10,398 total
includes taxes & fees
Nov 1 - Nov 2
Madison Beach Hotel
A deck with outdoor seating, overlooking a body of water with a sunset view.
Room
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

15. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Ann
The Pridwin Hotel
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A bar setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
A bar area with shelves stocked with various bottles and glasses.
A large, white, two-story building with a covered porch and a bicycle parked in front.

16. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$19,926
NT$22,877 total
includes taxes & fees
Oct 4 - Oct 5
Topping Rose House
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
A spacious room with a large bed, a staircase, and a door leading to another room.
A bar area with a long counter, multiple stools, and a well-stocked bar.
A hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

17. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,888
NT$10,221 total
includes taxes & fees
Oct 4 - Oct 5
Copper Beech Inn
A beach with waves gently lapping onto the shore.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.
A modern bedroom with a bed, a desk with a chair, a television, and a large mirror.
A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."

18. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
NT$18,934
NT$22,714 total
includes taxes & fees
Nov 1 - Nov 2
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
A restaurant with wooden beams, tables with white tablecloths, and a bar area.
A living room with a fireplace, a television mounted above it, and a dining area in the background.
A white house with a sign reading "The 1770 House Restaurant & Inn."

19. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$14,471
NT$19,782 total
includes taxes & fees
Oct 19 - Oct 20
The 1770 House Restaurant & Inn
A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.
A bedroom with a large window, a bed with beige bedding, and a view of greenery outside.
A modern kitchen with a light blue countertop, three wooden stools, and a framed artwork on the wall.
A modern interior with a wooden floor, a ceiling fan, a surfboard, and a counter with various items.

20. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Iryna
NT$13,160
NT$16,855 total
includes taxes & fees
Nov 1 - Nov 2
Offshore Spa & Residences
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Shelter Island.
Mill House Inn

Mill House Inn

31 North Main Street East Hampton NY
NT$10,353
NT$14,963 total
Oct 12 - Oct 13
includes taxes & fees
Mill House Inn
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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 coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island Hotel Reviews

Frequently asked questions

What are the best 4-star hotels in Shelter Island?
Make unforgettable memories in Shelter Island at Topping Rose House. A favorite with Expedia customers, this 4-star hotel offers loads of conveniences for a relaxing and comfortable stay.
How much does it cost to stay in a 4-star hotel in Shelter Island?
To lock in a 4-star hotel in Shelter Island that fits your budget, make use of Expedia's filters. Check out what's available during your preferred dates and use our pricing filter to set your maximum rate. You can also sort your results by the most economical option first.
  • Search for the lowest price from NT$14,963
What's the difference between 5-star and 4-star hotels in Shelter Island?
Treat yourself to luxury living during your Shelter Island getaway by choosing a 4-star hotel. As well as featuring upscale surroundings, these properties are typically packed with amenities such as large beds, complimentary bathrobes and plenty more. A 5-star hotel will go the extra mile to make your trip an even more lavish and memorable one. 24-hour concierge assistance, elegant décor and world-class dining are only the start of the exclusive conveniences and services you'll likely get access to.

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