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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Shelter Island 4-star hotels

A wooden pathway leading to a beach with a view of the ocean.
A house with a stone wall and a garden with various plants and flowers.
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.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
Amanda
NT$11,664
NT$15,992 total
includes taxes & fees
Nov 10 - Nov 11
Gurney's Montauk Resort & Seawater Spa
A spacious room with wicker furniture, large windows, and a view of the sea.
A coastal building with large windows, a deck, and a view of the sea at sunset.
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.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$5,803
NT$7,555 total
includes taxes & fees
Nov 16 - Nov 17
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 hotel room with two beds, a flat-screen TV, a ceiling fan, and a large sliding glass door leading to an outdoor area.

3. Offshore Montauk

Offshore Montauk
Montauk
United States
Mary
NT$4,491
NT$6,982 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 marina with boats docked, a grassy area with a tent, and houses in the background.
A deck with wicker chairs and a table, overlooking a beach with umbrellas and lounge chairs.
A beach with two sun loungers, a beach umbrella, and a basket.

4. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Sophie
NT$7,290
NT$12,027 total
includes taxes & fees
Nov 2 - Nov 3
Montauk Yacht Club
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A spacious living room with a fireplace, comfortable seating, and large windows.

5. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Thomas
NT$11,956
NT$15,026 total
includes taxes & fees
Nov 16 - Nov 17
Faraway Sag Harbor
A beachside patio with lounge chairs, umbrellas, and a wooden building with a balcony overlooking the ocean.
A hotel room with a large sliding glass door leading to an outdoor seating area, a bed with white bedding, a desk with a lamp, and a hanging light fixture.
A wooden building with a beach view, a wooden deck, and a sandy path leading to the beach.
A room with a large window overlooking a beach, a framed abstract artwork, and a lamp on a table.

6. Marram

Marram
Montauk
United States
paul
NT$6,562
NT$10,830 total
includes taxes & fees
Oct 25 - Oct 26
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 living room with a sofa, a wooden cabinet, a television, and a framed picture on the wall.
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
Emily
NT$6,853
NT$8,534 total
includes taxes & fees
Oct 25 - Oct 26
Hotel Corduroy
A lakeside patio with outdoor seating and a view of the water.
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.

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
NT$9,072
NT$10,365 total
includes taxes & fees
Nov 1 - Nov 2
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 modern kitchen with a central island, pendant lights, and a view of the outdoors.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.

9. Journey East Hampton

Journey East Hampton
East Hampton North
United States
Erika
NT$8,019
NT$10,078 total
includes taxes & fees
Nov 3 - Nov 4
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 living room with a sofa, a small table, a vintage refrigerator, and a large window with curtains.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
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$6,237
NT$7,482 total
includes taxes & fees
Nov 1 - Nov 2
The Maidstone
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.

11. Oyster Estate

Oyster Estate
Greenport
United States
Allison
NT$7,290
NT$9,185 total
includes taxes & fees
Oct 28 - Oct 29
Oyster Estate
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
A cozy room with a large window, a sofa, a small table with a tray, and a pair of slippers on the floor.
A beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.
A person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
Canada
Corrado
NT$15,390
NT$18,639 total
includes taxes & fees
Oct 21 - Oct 22
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 two-story building with a pool, outdoor seating, and potted plants.
A spacious living room with a high ceiling, wooden beams, a large sofa, a coffee table, and a dining area with stools.

13. Hero Beach Club

Hero Beach Club
Montauk
United States
Kevin
NT$5,978
NT$8,644 total
includes taxes & fees
Oct 20 - Oct 21
Hero Beach Club
A multi-story hotel with balconies and a beach view.
A grand staircase with a chandelier, a reception desk, and a fireplace.
A large hotel with multiple balconies and a beach area with sun loungers and umbrellas.
A beachside seating area with multiple Adirondack chairs and umbrellas, overlooking the ocean.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Eileen
NT$8,901
NT$10,236 total
includes taxes & fees
Nov 11 - Nov 12
Madison Beach Hotel
A deck with outdoor seating, overlooking a body of water with a sunset view.
A restaurant with green booths, wooden chairs, and round tables.
Room
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 large, white, two-story building with a covered porch and a bicycle parked in front.
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 modern hotel room with a bed, bedside table, and a view of the garden.

16. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$20,267
NT$23,268 total
includes taxes & fees
Oct 18 - Oct 19
Topping Rose House
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 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.

17. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$9,040
NT$10,396 total
includes taxes & fees
Oct 19 - Oct 20
Copper Beech Inn
A beach with waves gently lapping onto the shore.
A modern bedroom with a bed, a desk with a chair, a television, and a large mirror.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.
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
Dwight
NT$19,258
NT$23,103 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 garden pathway leading to a white picket fence and a building with an American flag.

19. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$13,041
NT$17,829 total
includes taxes & fees
Nov 1 - Nov 2
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 modern kitchen with a light blue countertop, three wooden stools, and a framed artwork on the wall.
A modern living room with a sofa, coffee table, and bar stools.
A bedroom with a large window, a bed with beige bedding, and a view of greenery outside.

20. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Frank
NT$12,218
NT$15,810 total
includes taxes & fees
Nov 8 - Nov 9
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$10,530
NT$15,219 total
Oct 18 - Oct 19
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"This was my first time staying @ this property. The staff were so kind & helpful! The gentleman at the front desk was beyond helpful from the moment we checked in, to the moment we left! This team knows the meaning of hospitality! 5 star service Would stay here again !! Thank you :)"
guadalupe 1-night trip
Posted 3 days ago
Offshore Montauk
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 4 days ago
Sound View Greenport

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$15,219
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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