Explore top 2026 4 Star Hotels in Shelter Island

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Top Shelter Island 4 Star hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
$395 nightly
The price is $452 total per night from Jan 20 to Jan 21
$452 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This resort features a private beach, a full-service spa, and 2 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside ...
8.2/10 Very Good! (705 reviews)
Good room. Great view! Nice heating system. Friendly staff.

Reviewed on Dec 27, 2025

Opens in a new windowGurney's Montauk Resort & Seawater Spa
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
$299 nightly
The price is $344 total per night from Jan 1 to Jan 2
$344 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the ...
9.4/10 Exceptional! (341 reviews)
beautiful room and views

Reviewed on Dec 13, 2025

Opens in a new windowMadison Beach Hotel
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
$181 nightly
The price is $207 total per night from Jan 1 to Jan 2
$207 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with ...
8.4/10 Very Good! (601 reviews)
Great room with amazing views! Staff was fantastic and the food was great too

Reviewed on Nov 28, 2025

Opens in a new windowSound View Greenport
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd Montauk NY
This hotel features a private beach, a marina, and 2 restaurants. Traveling on business? Take advantage of the 5 conference rooms, along with free WiFi in public ...
8.6/10 Excellent! (999 reviews)
Amazing property! Excellent service

Reviewed on Nov 27, 2025

Opens in a new windowMontauk Yacht Club
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

4 out of 5
239 E Montauk Hwy Hampton Bays NY
Fully refundableReserve now, pay when you stay
$417 nightly
The price is $477 total per night from Jan 24 to Jan 25
$477 total
Jan 24 - Jan 25, 2026
Total with taxes and fees
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like valet ...
9.8/10 Exceptional! (60 reviews)
Staff was amazing, food was delicious, decor and ambiance was beautiful, and the room was spotless. Check in and valet was so helpful. I will definitely be returning!

Reviewed on Nov 17, 2025

Opens in a new windowCanoe Place Inn and Cottages
Hero Beach Club

Hero Beach Club

4 out of 5
626 Montauk Hwy Montauk NY
This motel features a seasonal outdoor pool and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and onsite conference space. ...
9/10 Wonderful! (202 reviews)
Great weekend trip

Reviewed on Nov 29, 2025

Opens in a new windowHero Beach Club
Marram

Marram

4 out of 5
21 Oceanview Terrace Montauk NY
A seasonal outdoor pool, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and luggage storage ...
8.8/10 Excellent! (252 reviews)
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Reviewed on Nov 2, 2025

Opens in a new windowMarram
Journey East Hampton

Journey East Hampton

4 out of 5
490 Pantigo Road East Hampton NY
$193 nightly
The price is $221 total per night from Jan 6 to Jan 7
$221 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with a coffee shop and a garden. Enjoy the free on-the-go breakfast each morning. A picnic area, dry ...
9/10 Wonderful! (160 reviews)
Clean and simple

Reviewed on Dec 1, 2025

Opens in a new windowJourney East Hampton
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

4 out of 5
1400 Silvermere Rd Greenport NY
$203 nightly
The price is $231 total per night from Jan 4 to Jan 5
$231 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and 3 restaurants. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
9.8/10 Exceptional! (142 reviews)
absolutely charming and totally bats above its weight. splurge for the bungalow!

Reviewed on Dec 8, 2025

Opens in a new windowSilver Sands Motel & Beach Bungalows
The Roundtree, Amagansett

The Roundtree, Amagansett

4.5 out of 5
273 Main Street Amagansett NY
$624 nightly
The price is $713 total per night from Jan 1 to Jan 2
$713 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. There's fun for all ages with a playground ...
9.8/10 Exceptional! (91 reviews)
Very nice property, very nice food, and very nice service. Although the room was very nice and clean there was some maintenance needed in the bathroom area

Reviewed on Nov 13, 2025

Opens in a new windowThe Roundtree, Amagansett
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4 Star Hotels Shelter Island

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Shelter Island 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Shelter Island will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Shelter Island, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Shelter Island hotel reviews by fellow wanderers