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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Aug 25 - Aug 26
Tomorrow
Aug 26 - Aug 27
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Shelter Island 4-star hotels

A spacious room with wicker furniture, large windows, and a view of the sea.
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.
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
Suzanne
NT$7,992
NT$11,862 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport
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 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.

2. Montauk Yacht Club

Montauk Yacht Club
Montauk
United States
Annmarie
NT$11,187
NT$16,419 total
includes taxes & fees
Sep 22 - Sep 23
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 room with a large window overlooking a beach, a framed abstract artwork, and a lamp on a table.

3. Marram

Marram
Montauk
United States
Dana
NT$9,787
NT$17,555 total
includes taxes & fees
Sep 21 - Sep 22
Marram
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 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.

4. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
Montauk
United States
John
NT$27,411
NT$37,580 total
includes taxes & fees
Sep 21 - Sep 22
Gurney's Montauk Resort & Seawater Spa
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 room with a large window overlooking a natural landscape, a flat-screen TV mounted on the wall, and a wooden bench.
A swimming pool with lounge chairs and umbrellas, surrounded by a white building with multiple windows.

5. Offshore Montauk

Offshore Montauk
Montauk
United States
Jaime
NT$12,306
NT$17,701 total
includes taxes & fees
Sep 8 - Sep 9
Offshore Montauk
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 swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

6. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
NT$17,110
NT$21,503 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel
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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.

7. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
NT$22,805
NT$28,660 total
includes taxes & fees
Sep 15 - Sep 16
Faraway Sag Harbor
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.
A modern room with a blue accent wall, a sofa, a chair, a bed, and a small table with decorative items.
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$11,905
NT$14,961 total
includes taxes & fees
Sep 24 - Sep 25
Journey East Hampton
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.

9. Hero Beach Club

Hero Beach Club
Montauk
United States
Kwok Keet
NT$10,064
NT$14,739 total
includes taxes & fees
Sep 13 - Sep 14
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 white house with a red door, surrounded by a well-maintained garden with hedges and a stone pathway.
A garden statue of a seated figure with two potted plants on either side.

10. The Maidstone

The Maidstone
East Hampton
United States
Steven
NT$13,594
NT$16,308 total
includes taxes & fees
Sep 20 - Sep 21
The Maidstone
A multi-story hotel with balconies and a beach view.
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.
A coastal hotel with a pier, beach, and boats.

11. Madison Beach Hotel

Madison Beach Hotel
Madison Center
United States
Michael
NT$14,350
NT$16,503 total
includes taxes & fees
Sep 21 - Sep 22
Madison Beach Hotel
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 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$22,789
NT$27,599 total
includes taxes & fees
Sep 7 - Sep 8
Canoe Place Inn and Cottages
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.

13. Copper Beech Inn

Copper Beech Inn
Ivoryton
United States
Gregg
NT$8,893
NT$10,226 total
includes taxes & fees
Sep 14 - Sep 15
Copper Beech Inn
A seaside dining area with tables, chairs, and umbrellas, overlooking a body of water.
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.

14. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
NT$12,590
NT$14,384 total
includes taxes & fees
Sep 21 - Sep 22
Silver Sands Motel & Beach Bungalows
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.
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 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.

15. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
NT$31,411
NT$35,998 total
includes taxes & fees
Aug 31 - Sep 1
Topping Rose House
A modern living room with a sofa, a coffee table, and a view of the outdoors through large glass doors.
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.
A modern hotel lobby with a wooden floor, a reception desk, a surfboard display, and a refrigerated beverage cooler.

16. Offshore Spa & Residences

Offshore Spa & Residences
Downtown Montauk
United States
Frank
NT$27,223
NT$34,743 total
includes taxes & fees
Sep 7 - Sep 8
Offshore Spa & Residences
A beach with waves gently lapping onto the shore.
A house with a gravel driveway, a child holding an adult's hand, and a lamp post.
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 modern bedroom with a bed, a desk with a chair, a television, and a large mirror.

17. The Roundtree, Amagansett

The Roundtree, Amagansett
Amagansett North
United States
Tunca
NT$31,680
NT$38,004 total
includes taxes & fees
Sep 15 - Sep 16
The Roundtree, Amagansett
A modern multi-story building with large windows, a deck, and a staircase.
A deck with outdoor furniture, a pool, and a large umbrella.
A modern kitchen with white cabinetry, a marble countertop, and a view to the outdoors.
An outdoor deck with wicker furniture, a central table, and string lights.

18. Serenity at Shorewood

Serenity at Shorewood
East Hampton
Serenity at Shorewood
A four-poster bed with a green area rug, a white armchair, a television mounted on the wall, and a chandelier.
A room with a fireplace, a television mounted above it, and a round table with a bowl and a book.
A modern living room with a white sofa, a flat-screen TV mounted on the wall, a small console table with decorative items, and a patterned rug.
A wooden pier leading into calm waters with sailboats anchored in the distance.

19. James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
Old Saybrook Center
James Pharmacy Bed & Breakfast
A vase with orange flowers on a table.
A wooden staircase with a dog sign, a blue armchair, and a dining area in the background.
A two-story house with a front porch, a chimney, and a sign reading "Main Entrance."
A dog sitting on a floral-patterned sofa with a wooden coffee table in front.

20. 434 on Main

434 on Main
Amagansett North
United States
David
434 on Main
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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$27,889
NT$40,307 total
Sep 7 - Sep 8
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
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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 wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

Sound View Greenport

Sound View Greenport

8/10 Good
"The staff was very helpful and nice"
Katarzyna 3-night trip
Posted 1 day ago
Sound View Greenport
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Amazing hotel right next to the beach and we got to bring the pup too. Will def be back!"
Eryn 5-night trip
Posted 4 days ago
Offshore Montauk

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$40,307
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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