Lodging Image

Shelter Island 4 Stars Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island 4 Star Hotels

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Shelter Island 4-star hotels

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 coastal building with a deck extending over the water, featuring large windows and a dining area.

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$8,435
NT$10,544 total
includes taxes & fees
Oct 14 - Oct 15
Sound View Greenport
A wooden pathway leading to a beach with a view of the ocean.
An indoor swimming pool with a view of the beach, lounge chairs, and large windows.
A beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.
A modern living room with a sofa, a chair, a coffee table, and a view of the sea.

2. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$12,502
NT$17,141 total
includes taxes & fees
Sep 29 - Sep 30
Gurney's Montauk Resort & Seawater Spa
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 deck with wicker chairs and a table, overlooking a beach with umbrellas and lounge chairs.
A marina with boats docked, a grassy area with a tent, and houses in the background.

3. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Sophie
NT$6,975
NT$11,592 total
includes taxes & fees
Oct 18 - Oct 19
Montauk Yacht Club
A beachside patio with lounge chairs, umbrellas, and a wooden building with a balcony overlooking the ocean.
A poolside area with lounge chairs and orange umbrellas, 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.

4. Marram

Marram
Montauk
United States
NATAVAN
NT$7,333
NT$11,643 total
includes taxes & fees
Oct 12 - Oct 13
Marram
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 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.

5. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$5,115
NT$9,472 total
includes taxes & fees
Sep 29 - Sep 30
Offshore Montauk
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
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.

6. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$13,431
NT$16,880 total
includes taxes & fees
Oct 6 - Oct 7
Faraway Sag Harbor
A hotel room with a sofa, a coffee table, a TV, 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.
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$6,437
NT$8,016 total
includes taxes & fees
Oct 14 - Oct 15
Hotel Corduroy
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 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.

8. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
NT$8,771
NT$11,024 total
includes taxes & fees
Oct 18 - Oct 19
Journey East Hampton
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.

9. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Morris
The Pridwin Hotel
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 two-story building with a pool, outdoor seating, and potted plants.
A kitchen with a wooden countertop, three bar stools, a hanging light fixture, and a window with a view.

10. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$7,250
NT$10,061 total
includes taxes & fees
Oct 1 - Oct 2
Hero Beach Club
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.

11. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$9,256
NT$11,104 total
includes taxes & fees
Oct 18 - Oct 19
The Maidstone
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 breakfast buffet with various food items and beverages.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
United States
Carol
NT$15,082
NT$18,265 total
includes taxes & fees
Oct 6 - Oct 7
Canoe Place Inn and Cottages
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 beach with sun loungers and umbrellas, a sandy path, and a view of the water.
A grassy area with trees and a view of a body of water.

13. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sarah
NT$10,319
NT$11,790 total
includes taxes & fees
Oct 12 - Oct 13
Silver Sands Motel & Beach Bungalows
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 grand staircase with a chandelier, a reception desk, and a fireplace.
A covered porch with a view of the ocean, a wicker chair, and a small table.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$11,951
NT$13,743 total
includes taxes & fees
Oct 18 - Oct 19
Madison Beach Hotel
A poolside area with lounge chairs and yellow umbrellas.
A cozy interior with a wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.
A bedroom with a large bed, bedside tables, a window with curtains, and wooden shelving with various items.

15. Oyster Estate

Oyster Estate
Greenport
United States
Elizabeth
NT$10,034
NT$12,642 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.
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.
A spacious room with a large bed, a staircase, and a door leading to another room.

16. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,859
NT$10,188 total
includes taxes & fees
Sep 28 - Sep 29
Copper Beech Inn
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 setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.

17. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$31,292
NT$35,862 total
includes taxes & fees
Sep 28 - Sep 29
Topping Rose House
A beach with waves gently lapping onto the shore.
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.
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$22,045
NT$26,445 total
includes taxes & fees
Oct 6 - Oct 7
The Roundtree, Amagansett
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 modern hotel lobby with a wooden floor, a reception desk, a surfboard display, and a refrigerated beverage cooler.

19. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Iryna
NT$17,689
NT$23,837 total
includes taxes & fees
Oct 4 - Oct 5
Offshore Spa & Residences
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 white house with a sign reading "The 1770 House Restaurant & Inn."
A living room with a fireplace, a television mounted above it, and a dining area in the background.

20. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$14,423
NT$19,717 total
includes taxes & fees
Oct 19 - Oct 20
The 1770 House Restaurant & Inn
Save an average of 15% on thousands of hotels when you're signed in

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$27,783
NT$40,154 total
Sep 23 - Sep 24
includes taxes & fees
Mill House Inn
Casa Newmark Holiday home 7 BestStayz.1

Casa Newmark Holiday home 7 BestStayz.1

112 Northwest Path Sagaponack NY
Get ratesCasa Newmark Holiday home 7 BestStayz.1
Still don't see what you're looking for?
See all properties in Shelter Island.
You can also use these popular filters to refine your search.
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 17 hours 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$40,154
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.

Explore a world of travel with Expedia