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
Oct 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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
Amanda
NT$12,382
NT$16,976 total
includes taxes & fees
Nov 3 - Nov 4
Gurney's Montauk Resort & Seawater Spa
A spacious room with wicker furniture, large windows, and a view of 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.
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.

2. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$6,121
NT$7,905 total
includes taxes & fees
Nov 1 - Nov 2
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
Mary
NT$4,458
NT$6,930 total
includes taxes & fees
Nov 1 - Nov 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 deck with wicker chairs and a table, overlooking a beach with umbrellas and lounge chairs.
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$7,236
NT$11,938 total
includes taxes & fees
Nov 2 - Nov 3
Montauk Yacht Club
A pool area with umbrellas, potted plants, and a pathway leading to a building.
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.
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
Thomas
NT$12,067
NT$15,166 total
includes taxes & fees
Nov 8 - Nov 9
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 wooden building with a beach view, a wooden deck, and a sandy path leading to the beach.
A poolside area with lounge chairs and orange umbrellas, overlooking the ocean.

6. Marram

Marram
Montauk
United States
Noah
NT$7,960
NT$12,401 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 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$7,092
NT$8,832 total
includes taxes & fees
Oct 21 - Oct 22
Hotel Corduroy
A lakeside patio with outdoor seating and a view of the water.
Outdoor spa tub
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.

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
NT$8,939
NT$10,212 total
includes taxes & fees
Nov 3 - Nov 4
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
Erika
NT$7,901
NT$9,930 total
includes taxes & fees
Oct 20 - Oct 21
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 restaurant with multiple tables set for dining, a bar area, and framed artwork on the walls.
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$7,869
NT$9,440 total
includes taxes & fees
Oct 25 - Oct 26
The Maidstone
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
A wooden wall with a wall-mounted lamp, a shelf with decorative items, and a bedside table with a pillow.
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 modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

11. Oyster Estate

Oyster Estate
Greenport
United States
Allison
NT$7,183
NT$9,050 total
includes taxes & fees
Oct 25 - Oct 26
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 breakfast buffet with various food items and beverages.

12. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
Canada
Corrado
NT$15,276
NT$18,501 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 beach with white umbrellas arranged in a line.
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.

13. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$6,375
NT$9,070 total
includes taxes & fees
Oct 29 - Oct 30
Hero Beach Club
A multi-story hotel with balconies and a beach view.
A beachside seating area with multiple Adirondack chairs and umbrellas, overlooking the ocean.
A grand staircase with a chandelier, a reception desk, and a fireplace.
A grand staircase with a chandelier, a seating area with chairs and a table, and a sign indicating the location.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$7,986
NT$9,184 total
includes taxes & fees
Nov 11 - Nov 12
Madison Beach Hotel
A deck with outdoor seating, overlooking a body of water with a sunset view.
A restaurant with green booths, wooden chairs, and round tables.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.
Room

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 area with shelves stocked with various bottles and glasses.
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.

16. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$19,968
NT$22,926 total
includes taxes & fees
Oct 20 - Oct 21
Topping Rose House
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 bar area with a long counter, multiple stools, and a well-stocked bar.
A large, two-story house with a wrap-around porch and a conservatory.

17. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,907
NT$10,243 total
includes taxes & fees
Oct 15 - Oct 16
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 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.
A two-story house with a front porch, a white picket fence, and a sign that reads "The Roundtree."

18. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Dwight
NT$19,116
NT$22,932 total
includes taxes & fees
Nov 1 - Nov 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 white house with a sign reading "The 1770 House Restaurant & Inn."

19. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$12,945
NT$17,697 total
includes taxes & fees
Nov 1 - Nov 2
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 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.
A modern interior with a wooden floor, a ceiling fan, a surfboard, and a counter with various items.

20. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Frank
NT$12,128
NT$15,693 total
includes taxes & fees
Nov 1 - Nov 2
Offshore Spa & Residences
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$10,375
NT$14,995 total
Oct 19 - Oct 20
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"This was my first time staying @ this property. The staff were so kind & helpful! The gentleman at the front desk was beyond helpful from the moment we checked in, to the moment we left! This team knows the meaning of hospitality! 5 star service Would stay here again !! Thank you :)"
guadalupe 1-night trip
Posted 13 hours ago
Offshore Montauk
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 1 day 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$14,995
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