Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Barns
Bungalows
Cottages
Estates
Farmhouses
Hotels
Homes
Apartments
Boats
Cabins
Castles
Chalets
Condos
Lodges
Studios
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Shelter Island Cottage Rentals(11)

11 Results
$2,275 - $3,500
per week
Book it Now!
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
    (3)
    7 night minimum stay
    • 2 BR,
    • 1 BA,
    • Sleeps 6
      (6)
      14 night minimum stay
      • 3 BR,
      • 1 BA,
      • Sleeps 3
        2 - 7 night minimum stay
        • 2 BR,
        • 1 BA,
        • 1 HF BA,
        • Sleeps 6
          Book it Now!
          7 night minimum stay
          • 2 BR,
          • 1 BA,
          • Sleeps 6
            2 Reviews
            • 2 BR,
            • 1 BA,
            • Sleeps 6
              (15)
              $1,700
              per week
              Book it Now!
              7 night minimum stay
              • 3 BR,
              • 2 BA,
              • Sleeps 6
                1 Review
                11 - 41 night minimum stay
                • 4 BR,
                • 3 BA,
                • 1 HF BA,
                • Sleeps 7
                  7 - 14 night minimum stay
                  • 1 BR,
                  • 1 BA,
                  • Sleeps 4
                    7 night minimum stay
                    • 3 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 5
                      2 - 7 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 8
                        Advertisement
                         

                        Recent Shelter Island Reviews

                        Hidden Gem

                        5 of 5
                        • Submitted: Sep 8, 2013
                        • Stayed: Sep 2013

                        Perfect Getaway

                        5 of 5
                        In short this house is perfect. It combines the quaint charm of a cottage with all of the modern amenities one could wish for. Located in a peaceful, tree lined street, the garden totally private from all sides. Fluffy beds, comfy sofas, sunlight throughout. We have stayed here in both winter and summer months and in each season the house seems to offer exactly what we needed to relax and forget the city! A perfect base for either exploring the Hamptons, or enjoying the laid back atmosphere and natural life of Shelter Island.
                        • Submitted: May 24, 2013
                        • Stayed: Jun 2012