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

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Check availability on Shelter Island 4 Star Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

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, (814 reviews)
"Amazing resort. We had a great time at gurneys."
United States
russell
The price is Rp18.391.575
Rp25.214.804 total
includes taxes & fees
1 Jul - 2 Jul
Gurney's Montauk Resort & Seawater Spa
Ocean View 2 Queens | Premium bedding, down duvets, pillow-top beds, blackout curtains

Offshore Montauk

Offshore Montauk
4.0 star property
Montauk
9.2 out of 10, Wonderful, (144 reviews)
"Clean room but they don’t come in to clean the room during your stay. Very good air conditioning. Spa only has one working shower"
United States
Kathleen
The price is Rp12.308.898
Rp16.112.993 total
includes taxes & fees
20 Jul - 21 Jul
Offshore Montauk
Courtyard Balcony King | Courtyard view

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (257 reviews)
"Highly recommend"
Australia
Jasmin
The price is Rp10.577.398
Rp15.672.200 total
includes taxes & fees
30 Jun - 1 Jul
Marram
Resort view

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (659 reviews)
"Love being on the water"
United States
Gina
The price is Rp7.977.700
Rp10.652.057 total
includes taxes & fees
12 Jul - 13 Jul
Sound View Greenport
2 restaurants; breakfast, lunch and dinner served

Montauk Yacht Club

Montauk Yacht Club
4.5 star property
Montauk
8.6 out of 10, Excellent, (1,001 reviews)
"Truly amazing stay! Can’t wait to come back"
United States
Alexandra
The price is Rp11.304.090
Rp14.962.758 total
includes taxes & fees
15 Jul - 16 Jul
Montauk Yacht Club
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (89 reviews)
"Beautiful, calm and serene. What a nostalgic experience. We’re going back next weekend. A perfect weekend getaway from manhattan "
United States
Rita
The price is Rp10.660.959
Rp13.398.294 total
includes taxes & fees
1 Jul - 2 Jul
The Pridwin Hotel
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (184 reviews)
"Lovely hotel, great facilities and very welcoming staff. Thoroughly recommend."
United Kingdom
Dan
The price is Rp10.496.655
Rp13.191.737 total
includes taxes & fees
28 Jun - 29 Jun
Journey East Hampton
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

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
The price is Rp15.341.265
Rp19.280.067 total
includes taxes & fees
29 Jun - 30 Jun
Faraway Sag Harbor
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.2 out of 10, Very good, (162 reviews)
"It was very fantastic and the staff was very helpful. Late last night, my companion had need of feminine products and the staff was able to assist by giving her own. She was a lifesaver."
United States
Min
The price is Rp9.613.296
Rp11.532.523 total
includes taxes & fees
28 Jun - 29 Jun
The Maidstone
View from room

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (213 reviews)
"Love it"
United States
SOLMARY
The price is Rp10.317.225
Rp13.611.873 total
includes taxes & fees
30 Jun - 1 Jul
Hero Beach Club
Outdoor pool

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (152 reviews)
"Amazing"
United Kingdom
Ming Da
The price is Rp38.676.136
Rp44.250.286 total
includes taxes & fees
7 Jul - 8 Jul
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, (65 reviews)
"Peaceful beautiful stay. Wonderful staff. Wonderful restaurant."
United States
Micheal
The price is Rp12.829.245
Rp15.536.799 total
includes taxes & fees
29 Jun - 30 Jun
Canoe Place Inn and Cottages
Exterior

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (374 reviews)
"Exceptionally clean and wonderful staff"
United States
Bevin
The price is Rp10.813.028
Rp12.434.982 total
includes taxes & fees
8 Jul - 9 Jul
Madison Beach Hotel
Breakfast and dinner served

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (515 reviews)
"It could use an upgrade for the Breakfast menu."
United States
EUGENE
The price is Rp5.006.097
Rp5.757.012 total
includes taxes & fees
6 Jul - 7 Jul
Copper Beech Inn
Beach bar

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (156 reviews)
"Lovely lodging"
United States
Timothy
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
9.8 out of 10, Exceptional, (96 reviews)
"Fantastic hotel, great location."
United States
Tunca
The price is Rp26.824.785
Rp32.179.649 total
includes taxes & fees
21 Jul - 22 Jul
The Roundtree, Amagansett
Outdoor dining

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (167 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 Rp10.833.086
Rp14.809.434 total
includes taxes & fees
30 Jun - 1 Jul
The 1770 House Restaurant & Inn
One Bedroom Condo King with Ocean view | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is Rp20.544.735
Rp25.522.348 total
includes taxes & fees
21 Jul - 22 Jul
Offshore Spa & Residences
Front of property

The Farmhouse Bed and Breakfast

The Farmhouse Bed and Breakfast
4.0 star property
Cutchogue
10.0 out of 10, Exceptional, (14 reviews)
"very comfortable stay. "
United States
Valentine
The Farmhouse Bed and Breakfast
Villa, 3 Bedrooms, Pets allowed, Pool View | Exterior

Serenity at Shorewood

Serenity at Shorewood
4.0 star property
East Hampton
Serenity at Shorewood
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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 Rp16.219.754 per night from 12 Jul to 13 Jul
Rp16.219.754
Rp23.766.939 total
12 Jul - 13 Jul
includes taxes & fees
9/10 Wonderful! (85 reviews)
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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 wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great experience."
John 3-night trip
Posted 14 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 Rp23.766.939

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.