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 13 - Sep 14
Tomorrow
Sep 14 - Sep 15
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Shelter Island 4-star hotels

A spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A spacious room with large windows, a wooden bench, yoga mats, and a door leading to a balcony with a view of the sea.

1. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
NT$8,406
NT$10,508 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
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 beachfront property with multiple houses, including a large house with a balcony and smaller houses with wooden facades.

2. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$14,358
NT$19,685 total
includes taxes & fees
Oct 12 - Oct 13
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 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 beach with two sun loungers, a beach umbrella, and a basket.

3. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Annmarie
NT$6,971
NT$11,576 total
includes taxes & fees
Oct 15 - Oct 16
Montauk Yacht Club
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 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.

4. Marram

Marram
Montauk
United States
NATAVAN
NT$7,308
NT$14,676 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 room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.

5. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$7,234
NT$11,880 total
includes taxes & fees
Sep 15 - Sep 16
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 spacious living room with a fireplace, comfortable seating, and large windows.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

6. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
NT$14,667
NT$18,433 total
includes taxes & fees
Oct 4 - Oct 5
Faraway Sag Harbor
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 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
Dhurata
NT$6,415
NT$7,989 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 modern kitchen with a central island, pendant lights, and a view of the outdoors.
A pool area with lounge chairs and an umbrella, surrounded by lush greenery.
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$8,742
NT$10,986 total
includes taxes & fees
Oct 12 - Oct 13
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 restaurant with green booths, wooden chairs, and round tables.
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
Anna
NT$19,123
NT$24,032 total
includes taxes & fees
Sep 16 - Sep 17
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 beach with white umbrellas arranged in a line.
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$7,005
NT$11,221 total
includes taxes & fees
Oct 1 - Oct 2
Hero Beach Club
A two-story house with a front porch, columns, and a well-lit entrance.
A garden statue of a seated figure with two potted plants on either side.
A white house with a red door, surrounded by a well-maintained garden with hedges and a stone pathway.
A modern kitchen with a central island, bar stools, pendant lighting, and a view into the dining area.

11. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$8,655
NT$10,383 total
includes taxes & fees
Oct 13 - Oct 14
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 breakfast buffet with various food items and beverages.
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$15,031
NT$18,203 total
includes taxes & fees
Oct 5 - Oct 6
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.

13. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sirikhwan
NT$10,284
NT$11,750 total
includes taxes & fees
Oct 13 - Oct 14
Silver Sands Motel & Beach Bungalows
A multi-story hotel with balconies and a beach view.
A coastal hotel with a pier, beach, and boats.
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.

14. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$14,246
NT$16,382 total
includes taxes & fees
Oct 12 - Oct 13
Madison Beach Hotel
A poolside area with lounge chairs and yellow umbrellas.
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.
A modern outdoor seating area with a sofa, cushions, a wooden coffee table with a fire feature, and a decorative wall with geometric patterns.

15. Oyster Estate

Oyster Estate
Greenport
United States
Matthew
NT$12,278
NT$15,470 total
includes taxes & fees
Sep 15 - Sep 16
Oyster Estate
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.

16. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,829
NT$10,153 total
includes taxes & fees
Sep 16 - Sep 17
Copper Beech Inn
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 large, white, two-story building with a covered porch and a bicycle parked in front.
A modern hotel room with a bed, bedside table, and a view of the garden.

17. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$31,185
NT$35,740 total
includes taxes & fees
Sep 16 - Sep 17
Topping Rose House
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
Ryan
NT$21,970
NT$26,355 total
includes taxes & fees
Oct 1 - Oct 2
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 hotel lobby with a wooden floor, a reception desk, a surfboard display, and a refrigerated beverage cooler.
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.

19. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Iryna
NT$17,629
NT$23,756 total
includes taxes & fees
Oct 6 - Oct 7
Offshore Spa & Residences
An outdoor dining area with trees and tables under string lights.
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.
A restaurant with wooden beams, tables with white tablecloths, and a bar area.

20. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
NT$15,466
NT$21,143 total
includes taxes & fees
Sep 21 - Sep 22
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$27,689
NT$40,017 total
Sep 15 - Sep 16
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"We have been staying at the sound view for many years and our experience gets better every time!!! I highly recommend this place to stay!!!!"
Hristos 3-night trip
Posted 3 hours ago
Sound View Greenport
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Absolutely gorgeous stay!"
Sabrina 1-night trip
Posted 5 hours 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 7 hours 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$40,017
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