Shelter Island Hotel Guide - 4 Stars Hotels in Shelter Island, New York

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Check prices for these dates

Tonight
10 Nov - 11 Nov
Tomorrow
11 Nov - 12 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 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, (878 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is Rp6.646.237
Rp9.111.924 total
includes taxes & fees
24 Nov - 25 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, (768 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is Rp3.059.078
Rp4.011.434 total
includes taxes & fees
11 Nov - 12 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, (1,000 reviews)
"Excellent hotel, clean and spacious rooms, friendly and attentive staff."
United States
Svetlana
The price is Rp4.730.947
Rp7.469.148 total
includes taxes & fees
11 Nov - 12 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, (321 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is Rp5.615.392
Rp7.057.060 total
includes taxes & fees
6 Dec - 7 Dec
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, (234 reviews)
"Great stay"
United States
Alison
The price is Rp2.785.090
Rp4.215.071 total
includes taxes & fees
11 Nov - 12 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, (303 reviews)
"Fantastic!"
United States
Filipa
The price is Rp2.980.039
Rp7.433.852 total
includes taxes & fees
16 Nov - 17 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, (291 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)
"We loved our stay at Silver Sands! It was off season, so very quiet."
United States
Michael
The price is Rp3.978.700
Rp4.545.846 total
includes taxes & fees
6 Dec - 7 Dec
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 Rp3.399.980
Rp4.283.793 total
includes taxes & fees
15 Nov - 16 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, (211 reviews)
"Great place, convenient location, very friendly staff"
United States
Erika
The price is Rp2.791.335
Rp3.507.939 total
includes taxes & fees
22 Nov - 23 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, (399 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
The price is Rp4.878.971
Rp5.610.817 total
includes taxes & fees
23 Nov - 24 Nov
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 Rp3.707.425
Rp4.871.059 total
includes taxes & fees
19 Nov - 20 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, (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 Rp3.644.128
Rp4.371.755 total
includes taxes & fees
19 Nov - 20 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, (77 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 Rp8.409.525
Rp10.184.432 total
includes taxes & fees
3 Dec - 4 Dec
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 Rp11.312.167
Rp12.987.449 total
includes taxes & fees
11 Nov - 12 Nov
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 Rp5.045.715
Rp5.802.572 total
includes taxes & fees
11 Nov - 12 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 Rp10.748.738
Rp12.894.419 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, (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 Rp6.135.336
Rp8.387.280 total
includes taxes & fees
30 Nov - 1 Dec
The 1770 House Restaurant & Inn
A large, two-story house with a swimming pool, surrounded by dense trees and landscaped gardens.

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 Rp8.179.846
Rp9.345.605 total
includes taxes & fees
11 Nov - 12 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

Top Shelter Island Hotel Reviews

A pool area with umbrellas, potted plants, and a pathway leading to a building.
Faraway Sag Harbor

Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor

10/10 Excellent

Thoroughly enjoyed my stay at Baron's Cove. I stayed late February so the pool was closed, but this was expected. It's a motel style hotel where your door opens to the outside, but given the location of the hotel i felt perfectly safe. The Staff were fantastic, and always helpful. The breakfast was first class too. Sag Harbor is such an iconic place within the Hamptons and this hotel is just as iconic in my eyes. The decor, is photo-worthy. I certainly hope to come back again soon!
United Kingdom
Nathan
Reviewed February 28, 2025
Faraway Sag Harbor

Frequently Asked Questions

What are the best 4-star hotels in Shelter Island?

Kick back in upmarket comfort at Topping Rose House. Based on reviews by Expedia guests, this is one of Shelter Island's favourite 4-star hotels.

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's within your budget, take advantage of Expedia's search and sort filters. Browse what's available during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most budget-friendly escape first.

  • Search for the lowest price from Rp2.785.090

What's the difference between 5-star and 4-star hotels in Shelter Island?

Offering a welcoming guest experience and upscale décor, 4-star hotels are a fantastic option for your Shelter Island trip. These kinds of accommodation generally feature loads of handy amenities that make it simple to unpack and relax — think pillowtop mattresses, gyms and pools. Or enjoy even more lavishness at a 5-star hotel designed to pamper with luxury perks and amenities. On-site health clubs, oversized bathrooms and world-class dining are typically featured at these plush properties.

Does Shelter Island have any 4-star all-inclusive resorts?

Enjoy a relaxing holiday experience where just about everything is included in the one upfront price by using our "All inclusive" filter. Keeping to your budget is easy when your meals, accommodation and activities are already taken care of. Eager for more ideas? Check out the terrific offers on our standard 4-star hotels in and around Shelter Island.

Are there any 4-star casino hotels in Shelter Island?

To find your ideal escape in Shelter Island, simply use our convenient filter tools to refine your search. Offering resort-style amenities and a premium level of service, our 4-star casino hotels are a sure bet for a good time.