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Shelter Island

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Map of Shelter Island Hotels

Hotels (5)

B&Bs / Inns (8)

Specialty Lodging (0)

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13 Winthrop Road, Shelter Island, NY 11965
$180 - $475 Avg. price/night*
Ollie #1 of 5 hotels in Shelter Island
  •  Magical Shelter Island 
  • Shelter Island is magical and Dering Harbor Inn is one of the island's... more
  • November 20, 2013
Traveler photos (22)
3 Locust Ave., Shelter Island Heights, Shelter Island, NY 11965
House on Chase Creek Slideshow
$75 - $220 Avg. price/night*
Ollie #1 of 8 B&Bs / Inns in Shelter Island
  •  great find 
  • Romantic winter stay. Many restaurants were closed on SI, but 18 Bay had... more
  • March 11, 2014
Traveler photos (29)
11 Stearns Point Road, Shelter Island, NY 11965
$150 - $750 Avg. price/night*
Ollie #2 of 5 hotels in Shelter Island
Traveler photos (68)
81 Shore Road, Crescent Beach, Shelter Island, NY 11964
The Pridwin Hotel Slideshow
Show Prices
$187 - $453 Avg. price/night*
Ollie #3 of 5 hotels in Shelter Island
Professional photos | Traveler photos (38)
108 Rams Island Dr, Shelter Island, NY 11965
$105 - $250 Avg. price/night*
Ollie #4 of 5 hotels in Shelter Island
Traveler photos (37)
31 West Neck Road, Shelter Island, NY 11965
$160 - $975 Avg. price/night*
Ollie #2 of 8 B&Bs / Inns in Shelter Island
Traveler photos (27)
23 Grand Ave., Shelter Island Heights, Shelter Island, NY 11965
$300 Avg. price/night*
Ollie #3 of 8 B&Bs / Inns in Shelter Island
  •  CHARMING & QUAINT 
  • The Hotel is located right off the north ferry so the loccation is... more
  • August 15, 2013
Traveler photos (6)
Route 114 South, Shelter Island, NY
Ollie #4 of 8 B&Bs / Inns in Shelter Island
Traveler photos (15)
35 Shore Rd, Shelter Island, NY 11965
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$195 - $225 Avg. price/night*
Ollie #5 of 5 hotels in Shelter Island
  •  Picture perfect 
  • If you want a place RIGHT on the beach that has a youthful hip vibe with a... more
  • September 3, 2013
Professional photos | Traveler photos (8)
2 South Ferry Road, Shelter Island, NY 11965
Ollie #5 of 8 B&Bs / Inns in Shelter Island
7 Stearns Point Road, PO Box 648, Shelter Island Heights, Shelter Island, NY 11965
Ollie #6 of 8 B&Bs / Inns in Shelter Island
Traveler photos (1)
4 West Neck Road, Shelter Island, NY
$100 - $300 Avg. price/night*
Ollie #7 of 8 B&Bs / Inns in Shelter Island
Traveler photos (1)
18 Sylvan Road, Shelter Island, NY 11964
No photo provided
$165 - $225 Avg. price/night*