Photo by Brian V. Rowe

Find 4 Star Hotels in Shelter Island Heights, NY from $231

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Our top choices for Shelter Island Heights 4-star hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very Good, (697)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
$435 nightly
The price is $497
Dec 11 - Dec 12
Total with taxes and fees
Gurney's Montauk Resort & Seawater Spa

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
$242 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Beach Hotel

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
$218 nightly
The price is $249
Dec 24 - Dec 25
Total with taxes and fees
Sound View Greenport

Montauk Yacht Club

Montauk Yacht Club
4.0 star property
Montauk
8.6 out of 10, Excellent, (1000)
"Great hotel. Would like to come stay again in the summer."
United States
Stefania
Montauk Yacht Club

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
$422 nightly
The price is $483
Jan 9 - Jan 10, 2026
Total with taxes and fees
Canoe Place Inn and Cottages

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
"Great weekend trip "
United States
Timothy
$232 nightly
The price is $265
Dec 28 - Dec 29
Total with taxes and fees
Hero Beach Club

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

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
$223 nightly
The price is $255
Jan 5 - Jan 6, 2026
Total with taxes and fees
Journey East Hampton

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (141)
"Great get away "
United States
Charles
$203 nightly
The price is $231
Dec 24 - Dec 25
Total with taxes and fees
Silver Sands Motel & Beach Bungalows

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
$624 nightly
The price is $713
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Roundtree, Amagansett

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
$279 nightly
The price is $321
Dec 14 - Dec 15
Total with taxes and fees
Copper Beech 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
$279 nightly
The price is $363
Dec 14 - Dec 15
Total with taxes and fees
The 1770 House Restaurant & Inn

Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.2 out of 10, Wonderful, (136)
"Great rooms, staff and food"
United Kingdom
Alexandra
$547 nightly
The price is $629
Dec 15 - Dec 16
Total with taxes and fees
Topping Rose House

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
$278 nightly
The price is $318
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Maidstone

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

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
$437 nightly
The price is $499
Dec 11 - Dec 12
Total with taxes and fees
East Hampton Art House Bed & Breakfast

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (22)
"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
$302 nightly
The price is $335
Dec 21 - Dec 22
Total with taxes and fees
James Pharmacy Bed & Breakfast

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
$579 nightly
The price is $662
Dec 11 - Dec 12
Total with taxes and fees
Offshore Residences

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
$395 nightly
The price is $451
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Rams Head Inn

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
$1,798 nightly
The price is $2,055
Dec 21 - Dec 22
Total with taxes and fees
Canoe Place Waterfront Residences
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Explore similar 5-star hotels

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Learn more about Shelter Island Heights

Victorian homes line the streets of this charming hamlet where you can rent bikes to explore the island's quiet beaches. Reserve a table at one of the waterfront restaurants for sunset views or take the short ferry to Greenport for more dining options.

View of Dering Harbor
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Top Shelter Island Heights Hotel Reviews

Find out more about Shelter Island Heights

The beginning of any holiday starts with choosing a destination. Shelter Island Heights has become a popular destination with guests because it offers so much to keep you entertained. However, "location, location, location" applies to more than just your vacation destination. Now that you got a feeling for the area, it's time you to learn a little more about your home away from home.

Accommodations as Gorgeous as the City

Shelter Island Heights saw its fair share of visitors this past year. Our review section boast comments that will help you narrow down your pick. The resorts found here strive to make your vacation as enjoyable as your days and evenings exploring Shelter Island Heights. These hotels work to make the grounds and facilities welcoming from the time you step out of your car. You won't need to venture far to find a delicious lunch, to sustain your exercise routine, or for a refreshing swim during your stay with all they provide.

Rooms have been configured to keep you as comfortable as possible, with amenities like in-room tea or coffee, designer bathroom products, and ultra-comfortable bedding. So, sit back and relax. Moreover, if you find yourself in need of something further, you can rest easy the staff will work their best to ensure you continue to be happy during your time there. These hotels are so lovely that you'll regret the day you have to return home.

Book a 4-Star Hotel in Shelter Island Heights Today!

A trip to Shelter Island Heights should be a complete retreat from your daily routine. Reserve a 4-star hotel in Shelter Island Heights soon, because several other people are as well.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Shelter Island Heights?
We can help you easily track down the perfect 4-star hotel for your trip to Shelter Island Heights. Use our handy filter tool to fine-tune your search by things like price, amenities and star rating and get access to awesome deals in a couple of clicks.

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What's the difference between 5-star and 4-star hotels in Shelter Island Heights?
Offering a friendly traveler experience and upscale décor, 4-star hotels are a fantastic option for your Shelter Island Heights break. These types of stays generally feature lots of handy amenities that make it a breeze to kick back and relax — think pillowtop mattresses, restaurants and gyms. Or live the high life at a 5-star hotel designed to indulge you in luxury perks and amenities. Concierge assistance, complimentary toiletries and world-class dining are typically featured at these plush properties.
Does Shelter Island Heights have any 4-star all-inclusive resorts?
Finding your dream vacation in Shelter Island Heights is as easy as entering your travel dates and destination, and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodations, food, activities and entertainment, or go for a standard 4-star resort in or around this much-loved destination.

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