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Shelter Island 4 Stars Hotels

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Our top choices for Shelter Island 4-star hotels

A wooden pathway leading to a beach with a view of the ocean.

1. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very good, (880 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is NT$11,967
NT$16,407 total
includes taxes & fees
Dec 6 - Dec 7
Gurney's Montauk Resort & Seawater Spa
A spacious room with wicker furniture, large windows, and a view of the sea.

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (768 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is NT$4,901
NT$6,540 total
includes taxes & fees
Dec 14 - Dec 15
Sound View Greenport
A spacious bar area with a marble countertop, multiple bar stools, and a view of the marina through large windows.

3. Montauk Yacht Club

Montauk Yacht Club
4.5 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
United States
Svetlana
Montauk Yacht Club
A pool area with umbrellas, potted plants, and a pathway leading to a building.

4. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (322 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is NT$10,208
NT$12,829 total
includes taxes & fees
Dec 13 - Dec 14
Faraway Sag Harbor
A modern outdoor deck with lounge chairs and a view of the beach.

5. Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.2 out of 10, Wonderful, (235 reviews)
"Great stay"
United States
Alison
The price is NT$5,063
NT$7,663 total
includes taxes & fees
Nov 30 - Dec 1
Offshore Montauk
A beachside patio with lounge chairs, umbrellas, and a wooden building with a balcony overlooking the ocean.

6. Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (303 reviews)
"Fantastic!"
United States
Filipa
The price is NT$5,417
NT$13,514 total
includes taxes & fees
Nov 16 - Nov 17
Marram
A beach scene with two yellow and white striped beach chairs facing a fire pit on the sand.

7. Hotel Corduroy

Hotel Corduroy
4.0 star property
Culloden Shores
9.2 out of 10, Wonderful, (292 reviews)
"The place was clean and close to amenities. The designer paid attention to details with robes, gold bathroom fixtures, and even a hand written letter welcoming us. The water pressure as someone stated was great."
United States
Jason
Hotel Corduroy
A wooden pathway leading to beach chairs and umbrellas, surrounded by lush greenery and a view of the sea.

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (192 reviews)
"Amazing place to stay with a great location. We will definitely be back!"
United States
Kathleen
The price is NT$7,248
NT$8,281 total
includes taxes & fees
Dec 1 - Dec 2
Silver Sands Motel & Beach Bungalows
A cozy interior with a bar area, seating, and a fireplace.

9. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
The price is NT$5,918
NT$7,456 total
includes taxes & fees
Dec 9 - Dec 10
Oyster Estate
A modern building with a wooden exterior, a balcony, and a pathway lined with potted plants and stepping stones.

10. Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (213 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
The price is NT$7,264
NT$9,129 total
includes taxes & fees
Nov 22 - Nov 23
Journey East Hampton
A multi-story hotel with balconies and a beach view.

11. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.6 out of 10, Exceptional, (401 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
The price is NT$8,843
NT$10,169 total
includes taxes & fees
Nov 23 - Nov 24
Madison Beach Hotel
A beach with white umbrellas arranged in a line.

12. Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (253 reviews)
"Overall very pleasant experience."
United States
Kevin
The price is NT$6,740
NT$8,855 total
includes taxes & fees
Nov 29 - Nov 30
Hero Beach Club
A kitchen with a central island, two wicker chairs, and a bar area with glasses.

13. The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very good, (182 reviews)
"lovely hotel - would stay again but would ask for a back room as the noise from the very busy road is constant. Otherwise awesome amenities, loved that you had a ghd hairdryer and straighteners. Every where smelt divine! Breakfast was lovely and a decent coffee."
Australia
Clara
The price is NT$6,639
NT$7,964 total
includes taxes & fees
Nov 22 - Nov 23
The Maidstone
A tented area with a pool view, wooden lounge chairs, and a table with a drink and food.

14. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (78 reviews)
"We loved everything about this hotel… from the premises, decor, quality of food, respectful but friendly staff etc…Bravo!"
Canada
Corrado
The price is NT$15,288
NT$18,514 total
includes taxes & fees
Dec 11 - Dec 12
Canoe Place Inn and Cottages
A modern building with a pool, featuring a dining area with tables and chairs, and a glass entrance.

15. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (165 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is NT$20,565
NT$23,610 total
includes taxes & fees
Nov 18 - Nov 19
Topping Rose House
A large, two-story house with a wrap-around porch and a conservatory.

16. Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (530 reviews)
"Nice stay. Quite,"
United States
Joseph
The price is NT$9,173
NT$10,549 total
includes taxes & fees
Nov 15 - Nov 16
Copper Beech Inn
A beach with waves gently lapping onto the shore.

17. The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
9.8 out of 10, Exceptional, (101 reviews)
"Absolutely awesome place. Professional staff were extremely helpful. Pet and family friendly."
United States
Dwight
The price is NT$19,540
NT$23,441 total
includes taxes & fees
Dec 8 - Dec 9
The Roundtree, Amagansett
An outdoor dining area with trees and tables under string lights.

18. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (173 reviews)
"The room was beautiful, the location is great and the restaurant is just perfect. But what made the stay was the fabulous staff who made our stay! Many thanks and can't wait to return!"
United States
Leah
The price is NT$11,154
NT$15,247 total
includes taxes & fees
Nov 29 - Nov 30
The 1770 House Restaurant & Inn
A large, multi-story building with a swimming pool, outdoor seating, and a well-maintained garden.

19. East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65 reviews)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
The price is NT$14,870
NT$16,990 total
includes taxes & fees
Nov 23 - Nov 24
East Hampton Art House Bed & Breakfast
A lakeside property with a dock, a large building, and surrounding greenery.

20. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (128 reviews)
"Wonderful- so charming and comfortable; upscale yet casual"
United States
Ann
The Pridwin Hotel
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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
The price is NT$10,685 per night from Dec 6 to Dec 7
NT$10,685
NT$15,443 total
Dec 6 - Dec 7
includes taxes & fees
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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

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"One of my favorite hotels! Every detail was immaculate."
Melissa 1-night trip
Posted 19 hours ago
Faraway Sag Harbor
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Great stay at Offshore Hotel in Montauk. The king bed and pillows were most comfy! Edwardo got us beach chairs and we grabbed a bottle of wine to watch a perfect sunset, oceanside in November! Very close to restaurants and shopping. The sauna and red light therapy rooms in the wellness center a were a nice touch. Great spot for a 2 night getaway."
Jody 2-night trip
Posted 21 hours 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$15,443

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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