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Shelter Island 4 Stars Hotels

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Check availability on Shelter Island 4 Star Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Shelter Island 4-star hotels

Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very Good, (705)
"Good room. Great view! Nice heating system. Friendly staff. "
United States
Jessie
The price is NT$11,631
NT$15,946 total
includes taxes & fees
Jan 20 - 2026/1/21
Gurney's Montauk Resort & Seawater Spa
Exterior
Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (342)
"Wonderful staff"
United States
Rebecca
The price is NT$8,647
NT$9,944 total
includes taxes & fees
Jan 1 - 2026/1/2
Madison Beach Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (601)
"Great view but a gas station has a better breakfast. "
United States
Michael
The price is NT$5,000
NT$6,497 total
includes taxes & fees
Jan 12 - 2026/1/13
Sound View Greenport
Indoor pool, 2 outdoor pools
Montauk Yacht Club

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1001)
"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

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (60)
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages
View from room
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
The price is NT$7,638
NT$11,923 total
includes taxes & fees
Dec 31 - 2026/1/1
Hero Beach Club
Seasonal outdoor pool, pool umbrellas, sun loungers
Marram

Marram

Marram
4.0 star property
Montauk
8.8 out of 10, Excellent, (252)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
Marram
Exterior
Journey East Hampton

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.0 out of 10, Wonderful, (160)
"We were able to access many beaches with the beach pass that came with the stay. That was the main reason we wanted to stay there. The rooms were very nice, spacious and comfortable. "
United States
Sarah
Journey East Hampton
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Beach nearby, white sand, sun loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (91)
"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 NT$18,684
NT$22,413 total
includes taxes & fees
Jan 4 - 2026/1/5
The Roundtree, Amagansett
Breakfast and dinner served
Copper Beech Inn

Copper Beech Inn

Copper Beech Inn
4.0 star property
Ivoryton
8.6 out of 10, Excellent, (506)
"Very nice property. Very clean. Staff was very nice - very good breakfast. "
United States
Marilyn
The price is NT$8,762
NT$10,076 total
includes taxes & fees
Jan 1 - 2026/1/2
Copper Beech Inn
Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (161)
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is NT$9,264
NT$12,665 total
includes taxes & fees
Jan 12 - 2026/1/13
The 1770 House Restaurant & Inn
Outdoor pool
Topping Rose House

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (138)
"Our second home :)"
United States
olivia
The price is NT$16,817
NT$19,323 total
includes taxes & fees
Jan 24 - 2026/1/25
Topping Rose House
Garden
The Maidstone

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150)
"We had a wonderful stay "
United States
Sabrina
The price is NT$8,782
NT$10,034 total
includes taxes & fees
Jan 4 - 2026/1/5
The Maidstone
Seasonal outdoor pool, pool umbrellas, sun loungers
The Pridwin Hotel

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84)
"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

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
East Hampton Art House Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
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

Offshore Residences
4.5 star property
Downtown Montauk
The price is NT$15,057
NT$20,794 total
includes taxes & fees
Jan 1 - 2026/1/2
Offshore Residences
Exterior
The Rams Head Inn

The Rams Head Inn

The Rams Head Inn
4.0 star property
Shelter Island Heights
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
United States
Lana
The Rams Head Inn
Front of property
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NT$65,854
NT$79,753 total
includes taxes & fees
Dec 31 - 2026/1/1
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 NT$14,931 per night from Dec 31 to Jan 1
NT$14,931
NT$18,765 total
Dec 31 - 2026/1/1
includes taxes & fees
9/10 Wonderful! (75 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
Central Park summer

Top Shelter Island Hotel Reviews

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Good room. Great view! Nice heating system. Friendly staff. "
Jessie 1-night trip
Posted 2 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 NT$18,765

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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