Find 4 Star Hotels in Shelter Island, NY from ￥32,095

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Check availability on Shelter Island 4 Star Hotels

Our top choices for Shelter Island 4-star hotels

Exterior

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very Good, (736 reviews)
"Room was spotless, staff were great and the resort is top notch!!"
United States
Carrie
The price is ￥50,118
￥68,712 total
includes taxes & fees
Mar 12 - Mar 13
Gurney's Montauk Resort & Seawater Spa
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (620 reviews)
"Nice place"
United States
Mateusz
The price is ￥24,147
￥32,095 total
includes taxes & fees
Mar 26 - Mar 27
Sound View Greenport
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (347 reviews)
"Staff and hotel are lovely "
United States
Steven
The price is ￥34,821
￥40,044 total
includes taxes & fees
Mar 31 - Apr 1
Madison Beach Hotel
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (164 reviews)
"Amazing stay"
United States
Liana
The price is ￥27,507
￥34,571 total
includes taxes & fees
Mar 16 - Mar 17
Journey East Hampton
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (152 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is ￥38,974
￥44,528 total
includes taxes & fees
Mar 24 - Mar 25
The Maidstone
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (143 reviews)
"Our second home :)"
United States
olivia
The price is ￥75,235
￥86,509 total
includes taxes & fees
Mar 15 - Mar 16
Topping Rose House
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (148 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows
On the beach, sun loungers, beach towels

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (203 reviews)
"Great weekend trip "
United States
Timothy
The price is ￥25,021
￥44,670 total
includes taxes & fees
Apr 5 - Apr 6
Hero Beach Club
2 restaurants, breakfast served

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
"Wonderful hotel and location "
United States
FIONA
Montauk Yacht Club
2 restaurants, American cuisine

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (162 reviews)
"Wonderful Inn & staff…The restaurant is also excellent! "
United States
Anthony
The price is ￥41,912
￥57,299 total
includes taxes & fees
Mar 12 - Mar 13
The 1770 House Restaurant & Inn
Beach nearby, white sand, sun loungers, beach umbrellas

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (93 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is ￥93,828
￥112,558 total
includes taxes & fees
Mar 15 - Mar 16
The Roundtree, Amagansett
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The Pridwin Hotel
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is ￥47,685
￥52,930 total
includes taxes & fees
Apr 1 - Apr 2
James Pharmacy Bed & Breakfast
Exterior

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (509 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is ￥44,043
￥50,649 total
includes taxes & fees
Mar 12 - Mar 13
Copper Beech Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (62 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages
Exterior

Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (292 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
Faraway Sag Harbor
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is ￥75,615
￥104,425 total
includes taxes & fees
Mar 12 - Mar 13
Offshore Residences
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
Canoe Place Waterfront Residences
Exterior

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18 reviews)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Aerial view

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
East Hampton Art House Bed & Breakfast
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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
Central Park summer

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

8/10 Good
"I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly disappointed to get a call on our check In day to tell us the indoor pool could not be used. That was literally what we wanted to do for the weekend was relax at the pool and eat and drink. I booked the trips weeks prior so to get a call the day of saying we can’t use to pool during our stay was truly disappointing. They waived the resort fee for the inconvenience, otherwise the weekend was great. "
Tiffany 2-night trip
Posted 7 days ago
Gurney's Montauk Resort & Seawater Spa

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 ￥32,095

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.