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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

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

Our top choices for Shelter Island 4-star hotels

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.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$12,533
NT$17,183 total
includes taxes & fees
Sep 29 - Sep 30
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 coastal building with a deck extending over the water, featuring large windows and a dining area.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$7,965
NT$10,010 total
includes taxes & fees
Oct 25 - Oct 26
Sound View Greenport
A modern outdoor deck with lounge chairs and a view of the beach.
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.
A modern hotel with multiple balconies and large windows.

3. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$5,111
NT$7,652 total
includes taxes & fees
Sep 28 - Sep 29
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 numerous boats docked, a swimming pool, and a white building with a tower.
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.

4. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Sophie
NT$6,734
NT$11,327 total
includes taxes & fees
Oct 20 - Oct 21
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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

5. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$13,420
NT$16,866 total
includes taxes & fees
Oct 6 - Oct 7
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 room with a large window overlooking a beach, a framed abstract artwork, and a lamp on a table.
A poolside area with lounge chairs and orange umbrellas, overlooking the ocean.

6. Marram

Marram
Montauk
United States
NATAVAN
NT$7,327
NT$11,633 total
includes taxes & fees
Oct 12 - Oct 13
Marram
A hotel room with a sofa, a coffee table, a TV, 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.
A bedroom with a bed, bedside lamp, window with view, and a hanging tapestry.
A living room with a sofa, a wooden cabinet, a television, and a framed picture on the wall.

7. Hotel Corduroy

Hotel Corduroy
Culloden Shores
United States
Heather
NT$6,432
NT$8,010 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Corduroy
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
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.

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
NT$10,345
NT$11,819 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 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 living room with a fireplace, two sofas, a coffee table, and a chair.

9. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$7,981
NT$10,031 total
includes taxes & fees
Oct 18 - Oct 19
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.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,706
NT$10,444 total
includes taxes & fees
Oct 25 - Oct 26
The Maidstone
A cozy interior with a bar area, seating, and a fireplace.
A poolside area with lounge chairs and yellow umbrellas.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

11. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
NT$10,025
NT$12,631 total
includes taxes & fees
Oct 5 - Oct 6
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 person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.
A beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
NT$15,070
NT$18,250 total
includes taxes & fees
Oct 20 - Oct 21
Canoe Place Inn and Cottages
A bedroom with two beds, a wooden rocking chair, a small table, and a view of the outdoors.
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.
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$6,863
NT$9,622 total
includes taxes & fees
Sep 30 - Oct 1
Hero Beach Club
A multi-story hotel with balconies and a beach view.
A covered porch with a view of the ocean, a wicker chair, and a small table.
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.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$11,161
NT$12,835 total
includes taxes & fees
Oct 13 - Oct 14
Madison Beach Hotel
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.
A restaurant with green booths, wooden chairs, and round tables.

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 modern hotel room with a bed, bedside table, and a view of the garden.
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$19,845
NT$22,784 total
includes taxes & fees
Oct 6 - Oct 7
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 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.

17. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,881
NT$10,213 total
includes taxes & fees
Sep 29 - Sep 30
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 two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."
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.

18. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
NT$22,027
NT$26,424 total
includes taxes & fees
Oct 1 - Oct 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$14,459
NT$19,766 total
includes taxes & fees
Oct 22 - Oct 23
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 interior with a wooden floor, a ceiling fan, a surfboard, and a counter with various items.
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.

20. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Iryna
NT$17,675
NT$22,006 total
includes taxes & fees
Oct 4 - Oct 5
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$10,311
NT$14,902 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

Hotel Corduroy

Hotel Corduroy

10/10 Excellent
"Loved this hotel. Super clean, cute, comfy rooms. Loved the yard with the couches and fire pits. Would definitely come again."
Heather 2-night trip
Posted 4 days ago
Hotel Corduroy

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$14,902
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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