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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Shelter Island 4 Star Hotels

Tonight
28 Apr - 29 Apr
Tomorrow
29 Apr - 30 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

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, (762 reviews)
"Lovey hotel, great staff, perfect for families."
United States
Arthur
The price is Rp12.391.920
Rp16.989.322 total
includes taxes & fees
25 May - 26 May
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, (641 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
The price is Rp4.084.522
Rp6.144.198 total
includes taxes & fees
5 May - 6 May
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 stay. "
United States
Jeanne
The price is Rp3.427.046
Rp5.883.344 total
includes taxes & fees
13 May - 14 May
Montauk Yacht Club
Exterior

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 Rp5.673.262
Rp6.524.174 total
includes taxes & fees
11 May - 12 May
Madison Beach Hotel
Courtyard Balcony King | Courtyard view

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 Rp2.926.488
Rp6.791.078 total
includes taxes & fees
6 May - 7 May
Marram
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (171 reviews)
"Everything was excellent about this property"
United States
Guy
The price is Rp6.970.455
Rp8.760.227 total
includes taxes & fees
18 May - 19 May
Journey East Hampton
Property entrance

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 Rp6.893.005
Rp7.875.260 total
includes taxes & fees
5 May - 6 May
The Maidstone
View from room

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 Rp2.547.966
Rp4.664.318 total
includes taxes & fees
6 May - 7 May
Hero Beach Club
Outdoor pool

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 Rp10.765.480
Rp12.359.800 total
includes taxes & fees
7 May - 8 May
Topping Rose House
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
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, (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 Rp13.668.241
Rp16.396.829 total
includes taxes & fees
4 May - 5 May
The Roundtree, Amagansett
Beach bar

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
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 price is Rp5.559.153
Rp6.986.418 total
includes taxes & fees
10 May - 11 May
The Pridwin Hotel
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, (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 Rp6.432.611
Rp8.793.788 total
includes taxes & fees
12 May - 13 May
The 1770 House Restaurant & Inn
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
Breakfast and dinner served

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 Rp4.801.869
Rp5.522.149 total
includes taxes & fees
30 Apr - 1 May
Copper Beech Inn
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
9.2 out of 10, Wonderful, (26 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
James Pharmacy Bed & Breakfast
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 Rp10.068.435
Rp13.469.543 total
includes taxes & fees
5 May - 6 May
Offshore Residences
Reception hall

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
Garden

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
Sign in
Sign up, it's free

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 Rp7.744.950 per night from 10 May to 11 May
Rp7.744.950
Rp9.733.681 total
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (83 reviews)
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.
PoolSpaHot tubBreakfast includedWaterpark
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
Central Park summer

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"We had a wonderful time. Enjoyed the location, the food, the pool, and my wife loved her massage. "
John 3-night trip
Posted 11 hours ago
Gurney's Montauk Resort & Seawater Spa

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 Rp9.733.681

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.