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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
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 coastal building with large windows, a deck, and a view of the sea at sunset.
A seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

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 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.
An indoor swimming pool with a view of the beach, lounge chairs, and large windows.

2. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$14,596
NT$20,011 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$7,020
NT$11,632 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Yacht Club
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.

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 room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.
A hotel room with two beds, a flat-screen TV, a ceiling fan, and a large sliding glass door leading to an outdoor area.

5. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$7,212
NT$11,845 total
includes taxes & fees
Sep 13 - Sep 14
Offshore Montauk
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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

6. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
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 kitchen with a sink, a coffee maker, a vase with flowers, 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.

7. Hotel Corduroy

Hotel Corduroy
Culloden Shores
United States
jiayu
NT$7,066
NT$8,799 total
includes taxes & fees
Oct 11 - Oct 12
Hotel Corduroy
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A living room with a fireplace, two sofas, a coffee table, and a chair.
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.

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 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.

9. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
NT$15,995
NT$20,101 total
includes taxes & fees
Sep 14 - Sep 15
The Pridwin Hotel
A bedroom with two beds, a wooden rocking chair, a small table, and a view of the outdoors.
A kitchen with a wooden countertop, three bar stools, a hanging light fixture, and a window with a view.
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.

10. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$7,507
NT$11,794 total
includes taxes & fees
Oct 4 - Oct 5
Hero Beach Club
A two-story house with a front porch, columns, and a well-lit entrance.
A modern kitchen with a central island, bar stools, pendant lighting, and a view into the dining area.
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.

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 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.
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$15,031
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.
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
Sirikhwan
NT$10,284
NT$11,750 total
includes taxes & fees
Oct 12 - Oct 13
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 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$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 wooden bench, a sofa, and a bar area.
A cozy interior with a bar area, seating, and a fireplace.

15. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
NT$10,886
NT$13,715 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 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 hallway with a mirrored closet door, a wooden chair, and a vanity with a mirror and shelves.

16. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,802
NT$10,123 total
includes taxes & fees
Sep 14 - Sep 15
Copper Beech Inn
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 setting with a bartender and a customer. The bar has shelves with various bottles and glasses. There is a cushioned bench in the foreground.
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$31,093
NT$35,634 total
includes taxes & fees
Sep 16 - Sep 17
Topping Rose House
A beach with waves gently lapping onto the shore.
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 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."

18. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Ryan
NT$21,904
NT$26,277 total
includes taxes & fees
Oct 7 - Oct 8
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 modern kitchen with a light blue countertop, three wooden stools, and a framed artwork on the wall.

19. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Iryna
NT$17,577
NT$23,686 total
includes taxes & fees
Oct 7 - Oct 8
Offshore Spa & Residences
An outdoor dining area with trees and tables under string lights.
A restaurant with wooden beams, tables with white tablecloths, and a bar area.
A garden pathway leading to a white picket fence and a building with an American flag.
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$15,420
NT$21,080 total
includes taxes & fees
Sep 22 - Sep 23
The 1770 House Restaurant & Inn
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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$27,606
NT$39,898 total
Sep 13 - Sep 14
includes taxes & fees
Mill House Inn
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Casa Newmark Holiday home 7 BestStayz.1

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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

10/10 Excellent
"Everything went smoother than I thought it would. The staff couldn’t have been kinder, helpful, or more knowledgeable. The spa treatments and massages were off the charts! We’re looking forward to our next stay and many more to come!"
George 2-night trip
Posted 9 hours ago
Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Everything"
Tonya 1-night trip
Posted 1 day ago
Offshore Montauk
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 10 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$39,898
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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