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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Shelter Island 4-star hotels

A spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Suzanne
NT$7,994
NT$11,864 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport
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 beach with two sun loungers, a beach umbrella, and a basket.
A marina with boats docked, a grassy area with a tent, and houses in the background.

2. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Annmarie
NT$10,884
NT$16,067 total
includes taxes & fees
Sep 27 - Sep 28
Montauk Yacht Club
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.

3. Marram

Marram
Montauk
United States
Stephen
NT$9,772
NT$17,528 total
includes taxes & fees
Sep 22 - Sep 23
Marram
A wooden pathway leading to a beach with a view of the ocean.
A modern living room with a sofa, a chair, a coffee table, and a view of the sea.
An indoor swimming pool with a view of the beach, lounge chairs, and large windows.
A house with a stone wall and a garden with various plants and flowers.

4. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$28,372
NT$38,899 total
includes taxes & fees
Sep 21 - Sep 22
Gurney's Montauk Resort & Seawater Spa
A modern outdoor deck with lounge chairs and a view of the beach.
A modern hotel with multiple balconies and large windows.
A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.
A hotel room with two beds, a flat-screen TV, a ceiling fan, and a large sliding glass door leading to an outdoor area.

5. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$12,287
NT$17,674 total
includes taxes & fees
Sep 13 - Sep 14
Offshore Montauk
A deck with outdoor seating, overlooking a body of water with a sunset view.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

6. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
NT$17,113
NT$21,507 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel
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 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.

7. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
NT$22,809
NT$28,666 total
includes taxes & fees
Sep 15 - Sep 16
Faraway Sag Harbor
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.

8. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$11,886
NT$14,938 total
includes taxes & fees
Sep 23 - Sep 24
Journey East Hampton
A bedroom with two beds, a wooden rocking chair, a small table, and a view of the outdoors.
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.
A kitchen with a wooden countertop, three bar stools, a hanging light fixture, and a window with a view.

9. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$9,501
NT$14,091 total
includes taxes & fees
Sep 27 - Sep 28
Hero Beach Club
A two-story house with a front porch, columns, and a well-lit entrance.
A white house with a red door, surrounded by a well-maintained garden with hedges and a stone pathway.
A bathroom with two white robes hanging on a wooden rack, a window with a white blind, and a wooden towel rack with towels.
A garden statue of a seated figure with two potted plants on either side.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$13,596
NT$16,311 total
includes taxes & fees
Sep 21 - Sep 22
The Maidstone
A multi-story hotel with balconies and a beach view.
A grand staircase with a chandelier, a reception desk, and a fireplace.
A grand spiral staircase with a chandelier, a round table with chairs, and a blue sofa in a spacious lobby area.
A covered porch with a view of the ocean, a wicker chair, and a small table.

11. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$14,351
NT$16,504 total
includes taxes & fees
Sep 2 - Sep 3
Madison Beach Hotel
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.
A breakfast buffet with various food items and beverages.
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
United States
Carol
NT$22,754
NT$27,556 total
includes taxes & fees
Sep 20 - Sep 21
Canoe Place Inn and Cottages
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 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.

13. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,879
NT$10,211 total
includes taxes & fees
Aug 31 - Sep 1
Copper Beech Inn
A seaside dining area with tables, chairs, and umbrellas, overlooking 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 grassy area with trees and a view of a body of water.
A beach with sun loungers and umbrellas, a sandy path, and a view of the water.

14. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
NT$12,570
NT$14,362 total
includes taxes & fees
Sep 23 - Sep 24
Silver Sands Motel & Beach Bungalows
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
A modern hotel room with a bed, bedside table, and a view of the garden.
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.

15. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$31,417
NT$36,005 total
includes taxes & fees
Aug 31 - Sep 1
Topping Rose House
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 hotel lobby with a wooden floor, a reception desk, a surfboard display, and a refrigerated beverage cooler.
A modern kitchen with a light blue countertop, three wooden stools, and a framed artwork on the wall.

16. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Frank
NT$25,506
NT$32,783 total
includes taxes & fees
Sep 8 - Sep 9
Offshore Spa & Residences
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 patio with four wicker chairs arranged around a round table with a fire pit in the center, set in a grassy outdoor area with trees and a fence in the background.

17. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Tunca
NT$31,631
NT$37,946 total
includes taxes & fees
Sep 14 - Sep 15
The Roundtree, Amagansett
A modern multi-story building with large windows, a deck, and a staircase.
An outdoor deck with wicker furniture, a central table, and string lights.
A deck with outdoor furniture, a pool, and a large umbrella.
A spacious living area with a curved white sofa, a glass coffee table, and two blue armchairs with patterned cushions.

18. Serenity at Shorewood

Serenity at Shorewood
East Hampton
Serenity at Shorewood
A four-poster bed with a green area rug, a white armchair, a television mounted on the wall, and a chandelier.
A building labeled 'Little House Brewing Co.' with outdoor seating and a porch.
A modern living room with a white sofa, a flat-screen TV mounted on the wall, a small console table with decorative items, and a patterned rug.
A room with a fireplace, a television mounted above it, and a round table with a bowl and a book.

19. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
Old Saybrook Center
United States
Diane
James Pharmacy Bed & Breakfast
A vase with orange flowers on a table.
A two-story house with a front porch, a chimney, and a sign reading "Main Entrance."
A dog sitting on a floral-patterned sofa with a wooden coffee table in front.
A wooden staircase with a dog sign, a blue armchair, and a dining area in the background.

20. 434 on Main

434 on Main
Amagansett North
United States
David
434 on Main
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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$27,846
NT$40,245 total
Sep 13 - Sep 14
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 wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

Offshore Montauk

Offshore Montauk

10/10 Excellent
"None"
Vp 3-night trip
Posted 3 hours ago
Offshore Montauk
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Front desk team super nice and accommodating!"
Aldo 1-night trip
Posted 6 hours 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$40,245
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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