Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
27 Jan - 28 Jan
Tomorrow
28 Jan - 29 Jan
This weekend
30 Jan - 1 Feb
Next weekend
6 Feb - 8 Feb

Our top choices for Shelter Island 4-star hotels

Indoor pool, seasonal outdoor pool, pool loungers

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (720 reviews)
"Very nice place and atmosphere will definitely be there again "
United States
NASHAT
The price is HK$1,900
HK$2,606 total
includes taxes & fees
9 Feb - 10 Feb
Gurney's Montauk Resort & Seawater Spa
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (345 reviews)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is HK$1,912
HK$2,199 total
includes taxes & fees
5 Feb - 6 Feb
Madison Beach Hotel
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (608 reviews)
"Nice place"
United States
Mateusz
The price is HK$1,046
HK$1,418 total
includes taxes & fees
28 Jan - 29 Jan
Sound View Greenport
2 restaurants, breakfast served

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
"Great hotel. Would like to come stay again in the summer."
United States
Stefania
Montauk Yacht Club
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, (61 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages
View from room

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
Hero Beach Club
Courtyard view

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (252 reviews)
"We loved everything about our stay here: the beds are comfortable, the fire pits with the smores are a nice touch, the beach is very nice, the view as well; and the food is amazing. The staff is very helpful and friendly!"
Canada
Charlotte
Marram
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (162 reviews)
"Amazing stay"
United States
Liana
The price is HK$1,439
HK$1,808 total
includes taxes & fees
4 Feb - 5 Feb
Journey East Hampton
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (144 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows
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, (92 reviews)
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is HK$4,634
HK$5,559 total
includes taxes & fees
29 Jan - 30 Jan
The Roundtree, Amagansett
Breakfast and dinner served

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (506 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is HK$2,175
HK$2,502 total
includes taxes & fees
3 Feb - 4 Feb
Copper Beech Inn
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)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is HK$2,300
HK$3,145 total
includes taxes & fees
4 Feb - 5 Feb
The 1770 House Restaurant & Inn
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (140 reviews)
"Our second home :)"
United States
olivia
The price is HK$3,759
HK$4,321 total
includes taxes & fees
31 Jan - 1 Feb
Topping Rose House
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (150 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is HK$1,316
HK$1,504 total
includes taxes & fees
1 Feb - 2 Feb
The Maidstone
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
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)
"First class outstanding in every way"
United States
Steve
East Hampton Art House Bed & Breakfast
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
James Pharmacy Bed & Breakfast
Living area

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
The price is HK$3,735
HK$5,158 total
includes taxes & fees
28 Jan - 29 Jan
Offshore 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
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is HK$9,239
HK$11,189 total
includes taxes & fees
31 Jan - 1 Feb
Canoe Place Waterfront Residences
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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 HK$1,949 per night from 3 Feb to 4 Feb
HK$1,949
HK$2,450 total
3 Feb - 4 Feb
includes taxes & fees
8.8/10 Excellent! (78 reviews)
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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

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 HK$2,450

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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