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

Guest favourite
Room in Shelter Island Heights
SEVEN on Shelter - Queen Room w/Private Bathroom
1 bedroom, 1 bed, 1 shared bathroom
30 Aug – 4 Sept
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5.0 out of 5 average rating, 5 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, 41 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.93 out of 5 average rating, 85 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 76 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, 124 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Greenport
The Greenport Bungalow
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 294 reviews
Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Aug
Guest favourite
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds, 2.5 bathrooms
27 Aug – 1 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.96 out of 5 average rating, 98 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, 143 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Greenport
Cosy North Fork Cottage with large backyard
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 158 reviews
Top guest favourite
Guest suite in Greenport
Private Suite in a Greenport Historical Townhouse
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 122 reviews
Home in Sag Harbor
Shelter Island Shell Beach Oasis
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
4.92 out of 5 average rating, 95 reviews
Guest favourite
Home in Shelter Island
Mid-Century Gem with Pool. Steps to Private Beach.
3 bedrooms, 3 beds, 2.5 bathrooms
7–14 Sept
5.0 out of 5 average rating, 8 reviews