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4 Star Hotels in Shelter Island

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Featured 4 Star Shelter Island Hotels

Montauk Yacht Club
4 out of 5
  • 1 hour drive from Gardiner's Bay Country Club
The price is $365 per night from Sep 29 to Sep 30
$365
includes taxes & fees
Sep 29 - Sep 30
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
Baron's Cove
4 out of 5
  • 16 min drive from Gardiner's Bay Country Club
The price is $436 per night from Sep 8 to Sep 9
$436
includes taxes & fees
Sep 8 - Sep 9
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
Marram
4 out of 5
  • 1 hour drive from Gardiner's Bay Country Club
The price is $611 per night from Sep 8 to Sep 9
$611
includes taxes & fees
Sep 8 - Sep 9
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
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The Pridwin Hotel
4 out of 5
  • 9 min drive from Gardiner's Bay Country Club
The price is $409 per night from Oct 3 to Oct 4
$409
includes taxes & fees
Oct 3 - Oct 4
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
Sound View Greenport
4 out of 5
  • 11 min drive from Gardiner's Bay Country Club
The price is $429 per night from Sep 10 to Sep 11
$429
includes taxes & fees
Sep 10 - Sep 11
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
Gurney's Montauk Resort & Seawater Spa
4 out of 5
  • 56 min drive from Gardiner's Bay Country Club
The price is $948 per night from Sep 8 to Sep 9
$948
includes taxes & fees
Sep 8 - Sep 9
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
Journey East Hampton
4 out of 5
  • 35 min drive from Gardiner's Bay Country Club
The price is $409 per night from Sep 15 to Sep 16
$409
includes taxes & fees
Sep 15 - Sep 16
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
Copper Beech Inn
4 out of 5
Fully refundableReserve now, pay when you stay
  • 46 min drive from Gardiner's Bay Country Club
The price is $240 per night from Sep 9 to Sep 10
$240
includes taxes & fees
Sep 9 - Sep 10
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
Madison Beach Hotel
4 out of 5
Fully refundableReserve now, pay when you stay
  • 53 min drive from Gardiner's Bay Country Club
The price is $479 per night from Oct 7 to Oct 8
$479
includes taxes & fees
Oct 7 - Oct 8
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
Hero Beach Club
4 out of 5
Fully refundableReserve now, pay when you stay
  • 1 hour drive from Gardiner's Bay Country Club
The price is $478 per night from Oct 7 to Oct 8
$478
includes taxes & fees
Oct 7 - Oct 8
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
  • 45 min drive from Gardiner's Bay Country Club
The price is $593 per night from Oct 1 to Oct 2
$593
includes taxes & fees
Oct 1 - Oct 2
Stay at this 4-star spa hotel in Hampton Bays. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cooper's Beach and Meschutt Beach are ...
Canoe Place Inn and Cottages
Topping Rose House
4.5 out of 5
  • 26 min drive from Gardiner's Bay Country Club
The price is $1,253 per night from Sep 29 to Sep 30
$1,253
includes taxes & fees
Sep 29 - Sep 30
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
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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 $240 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.