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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
23–28 Aug
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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
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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
7–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Greenport
Corwin House
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.98 out of 5 average rating, 62 reviews
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
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, 125 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
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
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
Home in Greenport
Brand New Build! Greenport Gem w/ Yard & Patio
3 bedrooms, 3 beds, 3.5 bathrooms
3–8 Sept
New place to stay
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
Top guest favourite
Home in Greenport
Harbor Heights
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.94 out of 5 average rating, 241 reviews
Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Sept
Guest favourite
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
7–12 Aug
4.96 out of 5 average rating, 99 reviews
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 168 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, 10 reviews
Home in East Marion
The Gathering House | North Fork Retreat
4 bedrooms, 5 beds, 3.5 bathrooms
31 Aug – 5 Sept
New place to stay
Top guest favourite
Home in Greenport
Beach House in L.I. Wine Country
3 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 123 reviews