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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 Gardiner's Bay Country Club
The price is $710 per night from May 4 to May 5
$710
includes taxes & fees
May 4 - May 5
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
Baron's Cove
4 out of 5
  • 16 min drive from Gardiner's Bay Country Club
The price is $351 per night from May 11 to May 12
$351
includes taxes & fees
May 11 - May 12
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
Montauk Yacht Club
4 out of 5
  • 1 hour drive from Gardiner's Bay Country Club
The price is $273 per night from May 1 to May 2
$273
includes taxes & fees
May 1 - May 2
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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Journey East Hampton
4 out of 5
  • 35 min drive from Gardiner's Bay Country Club
The price is $481 per night from May 7 to May 8
$481
includes taxes & fees
May 7 - May 8
Stay at this 4-star hotel in East Hampton. Enjoy free breakfast, an outdoor pool, and free bicycles on site. Popular attractions Hither Hills State Park and ...
Journey East Hampton
Sound View Greenport
4 out of 5
  • 11 min drive from Gardiner's Bay Country Club
The price is $299 per night from May 13 to May 14
$299
includes taxes & fees
May 13 - May 14
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
Madison Beach Hotel
4 out of 5
  • 53 min drive from Gardiner's Bay Country Club
The price is $331 per night from May 6 to May 7
$331
includes taxes & fees
May 6 - May 7
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
Silver Sands Motel & Beach Bungalows
4 out of 5
  • 8 min drive from Gardiner's Bay Country Club
The price is $314 per night from May 1 to May 2
$314
includes taxes & fees
May 1 - May 2
Stay at this 4-star beach hotel in Greenport. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions ...
Silver Sands Motel & Beach Bungalows
Topping Rose House
4.5 out of 5
  • 26 min drive from Gardiner's Bay Country Club
The price is $455 per night from May 11 to May 12
$455
includes taxes & fees
May 11 - May 12
Stay at this 4.5-star luxury hotel in Bridgehampton. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions The Hamptons Beaches and Nancy ...
Topping Rose House
Marram
4 out of 5
  • 1 hour drive from Gardiner's Bay Country Club
The price is $468 per night from May 6 to May 7
$468
includes taxes & fees
May 6 - May 7
Stay at this 4-star beach hotel in Montauk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Montauk Point and South Edison Beach are ...
Marram
The Maidstone
4 out of 5
  • 32 min drive from Gardiner's Bay Country Club
The price is $508 per night from May 1 to May 2
$508
includes taxes & fees
May 1 - May 2
Stay at this 4-star boutique hotel in East Hampton. Enjoy free WiFi, free parking, and room service. Popular attractions The Hamptons Beaches and Home Sweet ...
The Maidstone
Canoe Place Inn and Cottages
4 out of 5
Fully refundableReserve now, pay when you stay
  • 45 min drive from Gardiner's Bay Country Club
The price is $660 per night from May 1 to May 2
$660
includes taxes & fees
May 1 - May 2
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 Pridwin Hotel
4 out of 5
  • 9 min drive from Gardiner's Bay Country Club
The price is $338 per night from May 18 to May 19
$338
includes taxes & fees
May 18 - May 19
Stay at this 4-star beach hotel in Shelter Island Heights. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
The Pridwin Hotel
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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 $273 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.