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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
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.
A house with a stone wall and a garden with various plants and flowers.
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.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$16,685
NT$22,874 total
includes taxes & fees
Oct 5 - Oct 6
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 beach bar with wooden chairs and a small table, overlooking 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.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$7,866
NT$9,894 total
includes taxes & fees
Oct 6 - Oct 7
Sound View Greenport
A modern outdoor deck with lounge chairs and a view of the beach.
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.
A room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.

3. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$5,978
NT$8,645 total
includes taxes & fees
Oct 1 - Oct 2
Offshore Montauk
A spacious bar area with a marble countertop, multiple bar stools, and a view of the marina through large windows.
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.
A marina with numerous boats docked, a swimming pool, and a white building with a tower.

4. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Sophie
NT$6,592
NT$11,172 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 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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

5. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$13,443
NT$16,894 total
includes taxes & fees
Oct 5 - Oct 6
Faraway Sag Harbor
A beachside patio with lounge chairs, umbrellas, and a wooden building with a balcony overlooking the ocean.
A wooden building with a beach view, a wooden deck, and a sandy path leading to the beach.
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 poolside area with lounge chairs and orange umbrellas, overlooking the ocean.

6. Marram

Marram
Montauk
United States
NATAVAN
NT$7,368
NT$11,699 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$6,443
NT$8,023 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.
Outdoor spa tub

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
NT$10,329
NT$11,801 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 living room with a fireplace, two sofas, a coffee table, and a chair.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.

9. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$7,969
NT$10,015 total
includes taxes & fees
Oct 13 - Oct 14
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 kitchen with a central island, two wicker chairs, and a bar area with glasses.
A restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,692
NT$10,427 total
includes taxes & fees
Oct 19 - Oct 20
The Maidstone
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 wooden reception desk with a notepad, a vase with dried flowers, and various decorative items on shelves above.
A sign for Oyster Estate with a tree in the background.
A poolside area with lounge chairs and yellow umbrellas.

11. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
NT$8,898
NT$11,211 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 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$15,096
NT$18,281 total
includes taxes & fees
Oct 6 - Oct 7
Canoe Place Inn and Cottages
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 beach with white umbrellas arranged in a line.

13. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$6,992
NT$9,767 total
includes taxes & fees
Oct 19 - Oct 20
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 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.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$11,180
NT$12,857 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.
Room
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

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 area with shelves stocked with various bottles and glasses.
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$19,878
NT$22,822 total
includes taxes & fees
Oct 5 - Oct 6
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 bar area with a long counter, multiple stools, and a well-stocked bar.
A spacious room with a large bed, a staircase, and a door leading to another room.

17. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,867
NT$10,197 total
includes taxes & fees
Oct 21 - Oct 22
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 modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

18. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
NT$22,064
NT$26,469 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
A garden pathway leading to a white picket fence and a building with an American flag.
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.

19. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$14,436
NT$19,735 total
includes taxes & fees
Oct 25 - Oct 26
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
Iryna
NT$17,705
NT$22,043 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$10,329
NT$14,928 total
Oct 15 - Oct 16
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

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 2 weeks ago
Faraway Sag Harbor

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$14,928
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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