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Shelter Island 4 Stars Hotels

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Our top choices for Shelter Island 4-star hotels

A wooden deck with a view of the sea, potted plants, and a modern building with large windows.

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, (879 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is NT$12,077
NT$16,557 total
includes taxes & fees
Nov 18 - Nov 19
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$4,888
NT$6,523 total
includes taxes & fees
Dec 14 - Dec 15
Sound View Greenport
A deck with wicker chairs and a table, overlooking a beach with umbrellas and lounge chairs.

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 NT$9,485
NT$14,587 total
includes taxes & fees
Nov 14 - Nov 15
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 NT$10,204
NT$12,823 total
includes taxes & fees
Dec 6 - Dec 7
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 NT$5,061
NT$7,659 total
includes taxes & fees
Nov 15 - Nov 16
Offshore Montauk
A wooden exterior wall with a window and a view of 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$5,415
NT$13,508 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 beach with sun loungers and umbrellas, a sandy path, and a view of the water.

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$7,230
NT$8,260 total
includes taxes & fees
Dec 1 - Dec 2
Silver Sands Motel & Beach Bungalows
A cozy interior with a wooden bench, a sofa, and a bar area.

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$5,915
NT$7,453 total
includes taxes & fees
Dec 2 - Dec 3
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 NT$5,406
NT$6,794 total
includes taxes & fees
Nov 18 - Nov 19
Journey East Hampton
A multi-story hotel with balconies, a well-maintained lawn, and a view of the beach at dusk.

11. Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.6 out of 10, Exceptional, (400 reviews)
"Beautiful hotel ,wonderful staff Everyone so kind, great customer service and breathtaking views and delicious food!"
United States
Eileen
The price is NT$8,866
NT$10,195 total
includes taxes & fees
Nov 23 - Nov 24
Madison Beach Hotel
A white building with a covered entrance, a weather vane, and a sign that reads "Hotel de la Mer."

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$6,737
NT$8,851 total
includes taxes & fees
Nov 19 - Nov 20
Hero Beach Club
A two-story house with a front porch, large windows, and a well-maintained lawn.

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$6,622
NT$7,944 total
includes taxes & fees
Nov 22 - Nov 23
The Maidstone
A large, two-story house with a prominent front porch and a stone retaining wall.

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$15,281
NT$18,506 total
includes taxes & fees
Dec 3 - Dec 4
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$20,555
NT$23,599 total
includes taxes & fees
Nov 14 - Nov 15
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$9,169
NT$10,544 total
includes taxes & fees
Nov 15 - Nov 16
Copper Beech Inn
A small, white door with a wooden exterior, a small porch, and a mailbox.

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$19,531
NT$23,430 total
includes taxes & fees
Nov 15 - Nov 16
The Roundtree, Amagansett
A large, two-story house with a well-maintained garden and a pathway leading to the entrance.

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$11,148
NT$15,240 total
includes taxes & fees
Nov 29 - Nov 30
The 1770 House Restaurant & Inn
A large estate with a swimming pool, multiple buildings, 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$14,863
NT$16,982 total
includes taxes & fees
Nov 16 - Nov 17
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$10,680 per night from Nov 16 to Nov 17
NT$10,680
NT$15,436 total
Nov 16 - Nov 17
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
"Clean room. AC was not working well and noisy. Overall very good"
Yohei 1-night trip
Posted 4 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$15,436

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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