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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
20–25 Sept
,
4.9 out of 5 average rating, 264 reviews
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
5 bedrooms, 6 beds, 1.5 bathrooms
9–14 Aug
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.97 out of 5 average rating, 120 reviews
Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
15–20 Jul
5.0 out of 5 average rating, 20 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
14–21 Jul
Home in Shelter Island
Captain Don’s Paradise
3 bedrooms, 4 beds, 1.5 bathrooms
3–8 Aug
4.92 out of 5 average rating, 13 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
Guest favourite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 76 reviews
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
4.93 out of 5 average rating, 84 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
23–28 Jul
4.91 out of 5 average rating, 93 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 8 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
4.91 out of 5 average rating, 141 reviews
Top guest favourite
Cottage in Greenport
3 Min Walk to Beach| 1 Mile to Town | Fam-Friendly
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 66 reviews
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Guest house in Shelter Island
Modern Waterfront Cottage Oasis
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Rooms in Greenport
Chestnut View Room own private bathroom
2 bedrooms, 3 queen beds, No bathroom
9–14 Aug
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
4.93 out of 5 average rating, 27 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Greenport
Beach House in L.I. Wine Country
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 121 reviews