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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
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.
A beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$16,671
NT$22,856 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 beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A beach bar with wooden chairs and a small table, overlooking the sea.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$7,947
NT$9,986 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 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 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$5,116
NT$7,659 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$6,802
NT$11,395 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Yacht Club
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 spacious living room with a fireplace, comfortable seating, and large windows.
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$13,432
NT$16,881 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 room with a large window overlooking a beach, a framed abstract artwork, and a lamp on a table.
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.

6. Marram

Marram
Montauk
United States
NATAVAN
NT$7,334
NT$11,644 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 living room with a sofa, a wooden cabinet, a television, 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 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$6,438
NT$8,017 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 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 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$10,320
NT$11,791 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 pool area with lounge chairs and an umbrella, surrounded by lush greenery.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.
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
NAKUL
NT$7,963
NT$10,007 total
includes taxes & fees
Oct 18 - Oct 19
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 room with a wicker sofa, a large potted plant, and a window with blinds.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,685
NT$10,419 total
includes taxes & fees
Oct 25 - Oct 26
The Maidstone
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.
A poolside area with sun loungers, a pool, and a building with a balcony.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.
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$10,035
NT$12,643 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 beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.
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.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
NT$15,084
NT$18,267 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 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.

13. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$6,846
NT$9,600 total
includes taxes & fees
Sep 28 - Sep 29
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 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.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$11,015
NT$12,667 total
includes taxes & fees
Oct 19 - Oct 20
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 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.
A bar area with shelves stocked with various bottles and glasses.

16. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$19,863
NT$22,804 total
includes taxes & fees
Sep 27 - Sep 28
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$8,860
NT$10,189 total
includes taxes & fees
Sep 28 - Sep 29
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 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$22,047
NT$26,448 total
includes taxes & fees
Oct 1 - Oct 2
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.
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."
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$14,425
NT$19,719 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 modern interior with a wooden floor, a ceiling fan, a surfboard, and a counter with various items.
A modern kitchen with a light blue countertop, three wooden stools, and a framed artwork on the wall.
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$17,691
NT$22,026 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$10,320
NT$14,916 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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"We stayed in the ocean front room. The room and view were beautiful. We had dinner at GIGIs. The food was good. The menu selection Was limited for us because we do not eat fish. The negative with Gurneys is the rooms are not connected to the main building. They do provide a car service to pick you up. I feel this limits you. We would have gone down for a drink but it seemed too involved to get there. This resort is not for seniors ."
salvatore 2-night trip
Posted 1 day ago
Gurney's Montauk Resort & Seawater Spa
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 13 days 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$14,916
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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