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

Superhost
Flat in Shelter Island Heights
Squire Chase House
3 bedrooms, 3 beds, 2 bathrooms
23–28 Aug
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4.9 out of 5 average rating, 263 reviews
Guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds
6–11 Sept
4.94 out of 5 average rating, 35 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds
13–20 Jul
New place to stay
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds
12–17 Jul
4.97 out of 5 average rating, 118 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 23 reviews
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds
1–6 Aug
4.92 out of 5 average rating, 12 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds
23–28 Jul
4.91 out of 5 average rating, 91 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds
5–10 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds
13–18 Sept
4.84 out of 5 average rating, 74 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds
13–18 Jul
4.93 out of 5 average rating, 83 reviews
Superhost
Home in Greenport
Stylish Getaway in Greenport
3 bedrooms, 3 beds
10–15 Aug
4.89 out of 5 average rating, 37 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds
15–20 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed
1–6 Sept
4.91 out of 5 average rating, 136 reviews
Villa in Shelter Island
Superb Shelter Island 4 bed Designer with a Pool
3 bedrooms, 4 beds
11–16 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Greenport
Beach House in L.I. Wine Country
3 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 119 reviews
Top guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds
2–7 Aug
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Rooms in Shelter Island
Grace House
2 bedrooms, 2 beds
13–18 Sept
5.0 out of 5 average rating, 48 reviews