Four Star Hotels in Shelter Island

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island 4 Star Hotels

This weekend
Next weekend

Our top choices for Shelter Island 4-star hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.4 out of 10, Very good, (764 reviews)
"Lovey hotel, great staff, perfect for families."
United States
Arthur
The price is RM1,966
RM2,695 total
includes taxes & fees
5 May - 6 May
Gurney's Montauk Resort & Seawater Spa

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1,000 reviews)
"Great stay. "
United States
Jeanne
The price is RM789
RM1,355 total
includes taxes & fees
12 May - 13 May
Montauk Yacht Club

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (642 reviews)
"Loved our stay. Our room was gorgeous a s in the perfect location. Would recommend and plan on coming back in the future!"
United States
Tara
Sound View Greenport

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (253 reviews)
"Beautiful resort in a great location "
United States
Nikki
The price is RM674
RM1,564 total
includes taxes & fees
4 May - 5 May
Marram

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (367 reviews)
"Lovely hotel for an off season visit."
United States
Delphine
The price is RM1,246
RM1,433 total
includes taxes & fees
11 May - 12 May
Madison Beach Hotel

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (172 reviews)
"Everything was excellent about this property"
United States
Guy
The price is RM1,807
RM2,271 total
includes taxes & fees
18 May - 19 May
Journey East Hampton

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (204 reviews)
"Great weekend trip "
United States
Timothy
The price is RM587
RM1,074 total
includes taxes & fees
5 May - 6 May
Hero Beach Club

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very good, (157 reviews)
"Bar was excellent "
United States
raje
The price is RM1,432
RM1,636 total
includes taxes & fees
5 May - 6 May
The Maidstone

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (149 reviews)
"Everything and everyone was just lovely! Comfortable Welcoming Great restaurant "
United States
Rachelle
The price is RM2,472
RM2,838 total
includes taxes & fees
7 May - 8 May
Topping Rose House

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

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (94 reviews)
"Thank you to the crew at The Roundtree for making our stay memorable! This is our second stay, so we couldn't turn down the evening smores by the fire and delivered warm cookies for a late night snack. The grounds and room were so beautiful. We will be back."
United States
Glenn
The price is RM3,138
RM3,765 total
includes taxes & fees
7 May - 8 May
The Roundtree, Amagansett

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 price is RM1,322
RM1,662 total
includes taxes & fees
27 May - 28 May
The Pridwin Hotel

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (152 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (164 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 RM1,477
RM2,019 total
includes taxes & fees
13 May - 14 May
The 1770 House Restaurant & Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (510 reviews)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is RM1,103
RM1,268 total
includes taxes & fees
5 May - 6 May
Copper Beech Inn

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

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (26 reviews)
"The fireplace was lovely and the room was cozy and attractive. The bathroom was spacious and clean, however we weren’t able to locate any extra t.p. I would advise people that the staircase going up to the rooms is quite steep. We were able to manage ok, but anyone with difficulty with stairs would have a challenge. The breakfast voucher for breakfast was great and we enjoyed a lovely meal. We also had a wonderful time at The Kate at a Blues concert. Overall, very satisfied with our overnight...
United States
pamela
James Pharmacy Bed & Breakfast

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is RM2,312
RM3,093 total
includes taxes & fees
6 May - 7 May
Offshore Residences

434 on Main

434 on Main
4.0 star property
Amagansett North
10.0 out of 10, Exceptional, (37 reviews)
"Great hosts"
United States
David
434 on Main

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
Save an average of 15% on thousands of hotels when you're signed in

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.
Still don't see what you're looking for?
See all properties in Shelter Island.
You can also use these popular filters to refine your search.
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.

Central Park summer

Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Take Your Pick of 4 Star Hotels in Shelter Island

The get-go of any holiday starts with choosing a great spot. Shelter Island has been a popular destination with guests because it offers so much to do and see. But, "location, location, location" applies to more than just what city where your plane lands. Now that you have a feel for the town, it's time you to get to know your new digs.

Accommodations as Picturesque as Shelter Island

Search Expedia.com.sg for the right 4 Star Shelter Island Hotel to suit your fancy. Plenty of these people wrote tips to help you select the accommodation that is the right fit for your holiday.You'll be more than glad to get back to your resort every night. Shelter Island has dozens of good options in the 4-star hotel range that create the ideal getaway.

A stay at one of these lodgings ensure that whether you are just relaxing after a day of checking out Shelter Island or you are ready to lie down for the night, you'll be as comfortable as possible. You won't go without a thing during your stay at one of these accommodations. Visitors have consistently given them high marks for their attentive service. It's no surprise that loads of guests recommend it.

Reserve a 4-Star Hotel in Shelter Island Today!

Your trip to Shelter Island should be one that you'll reminisce over for years to come, and booking a 4-star hotel will help create memories that are incredible. Make sure to make a reservation soon. With so few hotels, and plenty of people desiring to vacation in Shelter Island, you may miss out on your perfect hotel.

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 RM2,246

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.

Explore a world of travel with Expedia