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Search results; Over 1,000 homes in Shelter Island Heights

Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
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5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
2–7 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 155 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 31 reviews
Guest favourite
Rooms in Shelter Island
Room in Charming Coastal Cottage
2 bedrooms, 1 bed, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 26 reviews
Home in Shelter Island
Shelter Island's Silver Beach Home
3 bedrooms, 6 beds, 2.5 bathrooms
4–9 Sept
4.92 out of 5 average rating, 26 reviews
Guest favourite
Home in Shelter Island
Shelter Island Beauty w/Pool; Beaches/Golf/Tennis
4 bedrooms, 5 beds, 3.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Flat in Greenport
Harbor Heights
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 247 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.92 out of 5 average rating, 98 reviews
Home in Shelter Island
Bright beach house with private beach access
4 bedrooms, 5 beds, 2.5 bathrooms
3–8 Sept
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
5–10 Oct
4.93 out of 5 average rating, 87 reviews
Guest favourite
Room in Shelter Island Heights
SEVEN on Shelter - Queen Room w/Private Bathroom
1 queen bed, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 170 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 129 reviews
Top guest favourite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 29 reviews
Guest favourite
Home in Shelter Island
Family Friendly Modern Island Home Steps to Beach!
4 bedrooms, 7 beds, 3.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 15 reviews