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Check availability on Shelter Island 4 Star Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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, (876 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is 9.693.375 ₫
13.289.682 ₫ total
includes taxes & fees
3 Nov - 4 Nov
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, (762 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is 3.941.137 ₫
5.240.996 ₫ total
includes taxes & fees
15 Nov - 16 Nov
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, (1,004 reviews)
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
United States
Svetlana
The price is 5.995.701 ₫
9.800.235 ₫ total
includes taxes & fees
10 Nov - 11 Nov
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, (319 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is 8.258.755 ₫
10.379.118 ₫ total
includes taxes & fees
16 Nov - 17 Nov
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, (225 reviews)
"Great stay"
United States
Alison
The price is 3.980.746 ₫
6.024.624 ₫ total
includes taxes & fees
1 Nov - 2 Nov
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, (302 reviews)
"Fantastic!"
United States
Filipa
The price is 5.699.704 ₫
9.169.965 ₫ total
includes taxes & fees
8 Nov - 9 Nov
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, (289 reviews)
"Absolutely amazing!!"
United States
Emily
The price is 6.397.627 ₫
7.967.146 ₫ total
includes taxes & fees
30 Oct - 31 Oct
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, (186 reviews)
"Nicely renovated and enjoyable."
United States
Becky
The price is 7.237.720 ₫
8.269.094 ₫ total
includes taxes & fees
1 Nov - 2 Nov
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, (300 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is 5.479.988 ₫
6.904.525 ₫ total
includes taxes & fees
8 Nov - 9 Nov
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, (210 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
The price is 5.928.903 ₫
7.451.138 ₫ total
includes taxes & fees
9 Nov - 10 Nov
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, (396 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
The price is 6.987.243 ₫
8.035.330 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Madison Beach Hotel
A bedroom with two beds, a wooden rocking chair, a small table, and a view of the outdoors.

12. Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (250 reviews)
"Overall very pleasant experience."
United States
Kevin
The price is 5.111.300 ₫
7.286.687 ₫ total
includes taxes & fees
22 Nov - 23 Nov
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, (180 reviews)
"Great staff and amenities like restaurant"
United States
Steven
The price is 5.673.856 ₫
6.806.527 ₫ total
includes taxes & fees
5 Nov - 6 Nov
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, (76 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 14.604.685 ₫
17.686.984 ₫ total
includes taxes & fees
5 Nov - 6 Nov
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, (164 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is 16.159.167 ₫
18.552.266 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Topping Rose House
A conservatory with a glass ceiling, wooden furniture, and large windows offering a view of the garden.

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 7.211.871 ₫
8.293.652 ₫ total
includes taxes & fees
1 Nov - 2 Nov
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 15.355.090 ₫
18.420.256 ₫ total
includes taxes & fees
11 Nov - 12 Nov
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, (172 reviews)
"Beautiful property, we had a wonderful stay. Staff were very friendly and helpful, and the location is an easy walk to shops and restaurants."
United States
Lisa
The price is 9.661.064 ₫
13.207.289 ₫ total
includes taxes & fees
29 Nov - 30 Nov
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 11.691.503 ₫
13.357.730 ₫ total
includes taxes & fees
2 Nov - 3 Nov
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 8.396.050 ₫ per night from 11 Nov to 12 Nov
8.396.050 ₫
12.134.746 ₫ total
11 Nov - 12 Nov
includes taxes & fees
Still don't see what you're looking for?
See all properties in Shelter Island.
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PoolSpaHot tubBreakfast includedWaterpark
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
"Our experience was excellent! Eduardo was very helpful and accommodating! They are still under construction, so part of the property is unfinished and not accessible!"
Renee 2-night trip
Posted 3 days ago
Offshore Montauk
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."
Joan 2-night trip
Posted 7 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 favourite 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 12.134.746 ₫

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.