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Hotels in Shelter Island

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Choose from 4677 Shelter Island Hotel Deals

Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $208 per night from Apr 28 to Apr 29
$208
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,153 reviews)
"Beautiful hotel."

Reviewed on Apr 13, 2025

Montauk Manor
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
  • 35 min drive from Gardiner's Bay Country Club
The price is $91 per night from Apr 16 to Apr 17
$91
includes taxes & fees
Apr 16 - Apr 17
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (942 reviews)
"I liked the beach theme"

Reviewed on Apr 9, 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $247 per night from Apr 28 to Apr 29
$247
includes taxes & fees
Apr 28 - Apr 29
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 ...
8.4/10 Very Good! (1,003 reviews)
"When we checked out there was a "kid" at the pool who was I suppose looking after the area. It was raining and I was going to put my bags by the door. Before I knew it David came running up and asked if he could help me. This is a lesson in customer service. It's people like David and your other ..."

Reviewed on Apr 13, 2025

Montauk Yacht Club
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
  • 36 min drive from Gardiner's Bay Country Club
The price is $246 per night from Apr 16 to Apr 17
$246
includes taxes & fees
Apr 16 - Apr 17
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,003 reviews)
"Staff is always very receptive and cordial!"

Reviewed on Apr 10, 2025

Water's Edge Resort & Spa
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
  • 56 min drive from Gardiner's Bay Country Club
The price is $710 per night from Apr 27 to Apr 28
$710
includes taxes & fees
Apr 27 - Apr 28
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. ...
8.2/10 Very Good! (625 reviews)
"Beautiful property. We really enjoyed our stay!"

Reviewed on Apr 7, 2025

Gurney's Montauk Resort & Seawater Spa
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $170 per night from Apr 16 to Apr 17
$170
includes taxes & fees
Apr 16 - Apr 17
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,002 reviews)
"Very nice hotel, friendly and helpful staff. The room was spacious."

Reviewed on Apr 11, 2025

Hyatt Place Long Island East End
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
  • 16 min drive from Gardiner's Bay Country Club
The price is $300 per night from Apr 28 to Apr 29
$300
includes taxes & fees
Apr 28 - Apr 29
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 ...
9/10 Wonderful! (226 reviews)
"Excellent stay while visiting our son!"

Reviewed on Apr 10, 2025

Baron's Cove
The Harbor Front Inn
The Harbor Front Inn
3.5 out of 5
209 Front St, Greenport, NY
  • 6 min drive from Gardiner's Bay Country Club
The price is $211 per night from Apr 30 to May 1
$211
includes taxes & fees
Apr 30 - May 1
Stay at this 3.5-star business-friendly hotel in Greenport. Enjoy free breakfast, an outdoor pool, and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (446 reviews)
"Lovely space"

Reviewed on Apr 3, 2025

The Harbor Front Inn
Montauk Oceanside Suites
Montauk Oceanside Suites
3 out of 5
115 South Emerson Avenue, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $166 per night from Apr 17 to Apr 18
$166
includes taxes & fees
Apr 17 - Apr 18
Stay at this 3-star aparthotel in Montauk. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Montauk Point and South Edison Beach are ...
8.4/10 Very Good! (369 reviews)
"We stayed for a night and it was great. It was great location and setting. Overall stay was fantastic. Bathtub was a bit old, could not hold the water and if you are more than 1 person, you have to space your baths so you can all enjoy warm water."

Reviewed on Apr 6, 2025

Montauk Oceanside Suites
Saybrook Point Resort & Marina
Saybrook Point Resort & Marina
3.5 out of 5
2 Bridge St, Old Saybrook, CT
  • 32 min drive from Gardiner's Bay Country Club
The price is $375 per night from Apr 16 to Apr 17
$375
includes taxes & fees
Apr 16 - Apr 17
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,003 reviews)
"It was a quiet time of the year(off season) , remodel of the pool area was nice."

Reviewed on Apr 13, 2025

Saybrook Point Resort & Marina
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
  • 1 hour drive from Gardiner's Bay Country Club
The price is $182 per night from Apr 20 to Apr 21
$182
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Montauk Point and South Edison Beach are located ...
9.4/10 Exceptional! (40 reviews)
"Right on the beach, literally can't get closer. Clean. Nice pool. Great staff. Older structure but NOTHING feels old inside, all new flooring and everything is updated and pristine inside."

Reviewed on Apr 11, 2025

Montauk Blue Hotel
Sound View Greenport
Sound View Greenport
4 out of 5
58775 County Rd 48, Greenport, NY
  • 11 min drive from Gardiner's Bay Country Club
The price is $245 per night from Apr 28 to Apr 29
$245
includes taxes & fees
Apr 28 - Apr 29
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 ...
8.4/10 Very Good! (516 reviews)
"Beautiful setting"

Reviewed on Mar 31, 2025

Sound View Greenport
See all 4,677 properties in Shelter Island
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.

Find cheap hotels in Shelter Island

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