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

Top guest favourite
Home in Shelter Island Heights
Laid Back Relaxation
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
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5.0 out of 5 average rating, 22 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, 129 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, 43 reviews
Superhost
Home in Shelter Island
Light- filled historic home -walk to water-pool
6 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 bedrooms, 4 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
5 bedrooms, 9 beds, 3.5 bathrooms
4–9 Oct
4.95 out of 5 average rating, 79 reviews
Home in Shelter Island
Waterfront Retreat | Spa Pool, Sauna & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
8–13 Sept
New place to stay
Guest favourite
Flat in Greenport
Harbor Heights
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 247 reviews
Guest favourite
Home in Greenport
Cosy North Fork Cottage with large backyard
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.98 out of 5 average rating, 163 reviews
Home in Shelter Island
NEW RENTAL: MAGICAL SHELTER ISLAND RETREAT
5 bedrooms, 8 beds, 4.5 bathrooms
30 Sept – 7 Oct
Guest favourite
Home in Shelter Island
Shelter Island Home with Large Yard And Pool
3 bedrooms, 6 beds, 2 bathrooms
9–16 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Shelter Island Heights
Luxury Resort Style Pool Oasis, Walk To Beach
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 22 reviews
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 bedrooms, 3 beds, 2 bathrooms
20–27 Sept
5.0 out of 5 average rating, 77 reviews
Guest favourite
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
4 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Greenport
Upscale Newly Constructed Apartment
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
4.96 out of 5 average rating, 178 reviews
Guest favourite
Home in Shelter Island
Shelter Island Retreat | 3 King Beds + Huge Yard
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Greenport
Corwin House
4 bedrooms, 4 beds, 3 bathrooms
12–18 Oct
4.98 out of 5 average rating, 66 reviews