Best Family Escapes - Vacation Rentals in Shelter Island Historical Society

'The Gate House'on Beach front Estate with Dockage. Walk to Village . From US $315
         

House on Chase Creek From US $421
         

9.4 (83 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Cottage on Beach front Estate Walk to Village From US $164
         

9.8 (85 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Seven Resort Style Inn near Beach From US $341
         

|
9.9 (93 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor Knoll Bed & Breakfast From US $330
         

|
9.4 (14 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • Private Pool
House on Chase Creek From US $367
         

|
9.2 (15 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
West Neck Guesthouse From US $358
         

|
8.2 (41 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Blue Bay Dream w/Seasonal Outdoor Jacuzzi, Cabana + Office From US $486
         

10.0 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Shelter Island Retreat w/Outdoor Pool! From US $1,594
         

Fishermans Cottage near Crescent Beach From US $455
         

Beach Block Hideaway From US $414
         

10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
The SandPiper From US $381
         

9.8 (38 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Harbor Heights From US $171
         

9.8 (14 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Bright and Spacious Summer Home Steps from the Beach From US $690
         

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Weather in Shelter Island Historical Society

View the weather forecast for Shelter Island Historical Society before booking your Shelter Island Historical Society Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Shelter Island Historical Society Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Shelter Island Historical Society?
How many vacation rentals are available in Shelter Island Historical Society?

Currently, the total number of properties listed in 2026 is over 320 in the Shelter Island Historical Society area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Shelter Island Historical Society.