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4 Star Hotels in Shelter Island

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Featured 4 Star Shelter Island Hotels

Gurney's Montauk Resort & Seawater Spa
4 out of 5
  • 56 min drive from Shelter Island Historical Society
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the room service in our reviews. ...
Gurney's Montauk Resort & Seawater Spa
Sound View Greenport
4 out of 5
  • 12 min drive from Shelter Island Historical Society
The price is $205 per night from Dec 23 to Dec 24
$205
includes taxes & fees
Dec 23 - Dec 24
Stay at this 4-star beach hotel in Greenport. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Sound View Greenport
Baron's Cove
4 out of 5
  • 12 min drive from Shelter Island Historical Society
The price is $316 per night from Dec 22 to Dec 23
$316
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Baron's Cove
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Journey East Hampton
4 out of 5
  • 32 min drive from Shelter Island Historical Society
The price is $252 per night from Jan 1 to Jan 2
$252
includes taxes & fees
Jan 1 - Jan 2, 2025
Stay at this 4-star hotel in East Hampton. Enjoy free breakfast, an outdoor pool, and free bicycles on site. Popular attractions East Hampton Historical Society ...
Journey East Hampton
Madison Beach Hotel
4 out of 5
  • 56 min drive from Shelter Island Historical Society
The price is $344 per night from Dec 22 to Dec 23
$344
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star beach hotel in Madison. Enjoy free WiFi, a full-service spa, and a private beach. Our guests praise the helpful staff and the property condition ...
Madison Beach Hotel
Topping Rose House
4.5 out of 5
  • 22 min drive from Shelter Island Historical Society
The price is $474 per night from Jan 5 to Jan 6
$474
includes taxes & fees
Jan 5 - Jan 6, 2025
Stay at this 4.5-star luxury hotel in Bridgehampton. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Nancy + Co. and Children's Museum ...
Topping Rose House
Copper Beech Inn
4 out of 5
Fully refundableReserve now, pay when you stay
  • 50 min drive from Shelter Island Historical Society
The price is $240 per night from Dec 29 to Dec 30
$240
includes taxes & fees
Dec 29 - Dec 30
Stay at this 4-star hotel in Ivoryton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Copper Beech Inn
Marram
4 out of 5
  • 1 hour drive from Shelter Island Historical Society
Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions South Edison Beach and Kirk Park Beach are ...
Marram
Hero Beach Club
4 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Shelter Island Historical Society
The price is $345 per night from Dec 26 to Dec 27
$345
includes taxes & fees
Dec 26 - Dec 27
Stay at this 4-star beach motel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Second House Museum and Kirk Park Beach are ...
Hero Beach Club
Canoe Place Inn and Cottages
4 out of 5
Fully refundableReserve now, pay when you stay
  • 41 min drive from Shelter Island Historical Society
The price is $358 per night from Dec 22 to Dec 23
$358
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star spa hotel in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Meschutt Beach and Sebonack Golf Course ...
Canoe Place Inn and Cottages
The 1770 House Restaurant & Inn
4 out of 5
  • 29 min drive from Shelter Island Historical Society
The price is $342 per night from Dec 22 to Dec 23
$342
includes taxes & fees
Dec 22 - Dec 23
Stay at this 4-star inn in East Hampton. Enjoy free WiFi, free parking, and 2 restaurants. Popular attractions Guild Hall and Home Sweet Home Museum are located ...
The 1770 House Restaurant & Inn
Montauk Yacht Club
4 out of 5
  • 1 hour drive from Shelter Island Historical Society
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition ...
Montauk Yacht Club
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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.

4-star hotels in Shelter Island

When you want to live it up, but not bust your bank account, then there’s nothing better than a 4-star hotel in Shelter Island for your next trip. You’ll get all the amenities you can think of (and then some) at a rate within your means.

No fault in our stars

So what’s with the star rating anyway? Good question. The star rating has little to do with the price, and more to do with the amenities. 4-Star hotels in Shelter Island as well as everywhere else, usually have all those thoughtful touches that make you go “Ooh,” “Ahh,” and ”YES!” Think amenities like luxury bedding, high-end electronics, concierge service, and restaurants that make eating in a gourmet experience.

Stars that shine

You know there are as many underground spots, inviting lounges, memory-making music venues as there are stars in the sky. But you’ll need the funds to check them all off. That’s why we give you the chance to take us up on the Hotwire Hot Rate. You can snag Shelter Island 4-star hotels and still have plenty of leftover cash to paint the town whatever color you want. Filter hotels by:

  • Hotwire Hot Rate: We’ll snag you a crazy deal on a room by finding your hotel name after you book.
  • Price: You know that paying full price is for suckers? You can get a cheap 4-star hotel in Shelter Island starting at $205 per night.
  • Amenities: What makes you flip for your trip? Full-service spa? Heated pool? 24-hour room service? Get a hotel that’ll send you over the moon.

Do you deserve a swanky hotel with a ton of amenities? Yes, yes you do. And you also deserve a sweet deal on it. Book with Hotwire today and get that star-studded Shelter Island 4-star hotel and have plenty of cash left over to spend at that secret super star joint in the city.