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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
20–25 Sept
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5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds
9–14 Sept
5.0 out of 5 average rating, 11 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
14–19 Sept
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds
9–14 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Shelter Island
Family Friendly Modern Island Home Steps to Beach!
4 bedrooms, 7 beds
10–15 Sept
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 bed waterfront home with office
4 bedrooms, 5 beds
21–26 Sept
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
26 Sept – 1 Oct
4.97 out of 5 average rating, 129 reviews
Home in Shelter Island
Shelter Island - Modern 4 Bed Home Close to Beach
4 bedrooms, 4 beds
10–15 Sept
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed
4–9 Oct
4.92 out of 5 average rating, 159 reviews
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds
5–10 Oct
4.93 out of 5 average rating, 87 reviews
Guest favourite
Home in Shelter Island
Shelter Island Beauty w/Pool; Beaches/Golf/Tennis
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds
9–14 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Room in Shelter Island
Master Suite at RedHouse
1 king bed
25–30 Sept
4.94 out of 5 average rating, 171 reviews
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
6 bedrooms
11–16 Sept
5.0 out of 5 average rating, 8 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds
9–14 Sept
New place to stay
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 77 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Home in Shelter Island
Shelter Island's Silver Beach Home
3 bedrooms, 6 beds
10–15 Sept
4.92 out of 5 average rating, 26 reviews