filters

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

Loft in Shelter Island Heights
Waterfront jewel box on a high bluff.
1 bedroom, 2 beds, 1 shared bathroom
8–15 Sept
,
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
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
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–12 Aug
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
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, 124 reviews
Home in Sag Harbor
Shelter Island Shell Beach Oasis
4 bedrooms, 5 beds, 3 bathrooms
5–10 Aug
New place to stay
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
Flat in Greenport
Greenport Harbor Apartment
3 bedrooms, 4 beds, 2 bathrooms
5–10 Aug
4.96 out of 5 average rating, 99 reviews
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
Superhost
Home in East Marion
Bungalow by the Bay
2 bedrooms, 2 queen beds, 1.5 bathrooms
22–27 Sept
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
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
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, 122 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
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 bedroom, 1 queen bed, 1 bathroom
2–7 Sept
4.92 out of 5 average rating, 143 reviews
Top guest favourite
Home in Greenport
Cosy North Fork Cottage with large backyard
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 158 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.92 out of 5 average rating, 95 reviews
Top guest favourite
Home in Shelter Island
Newly Renovated w/ Pool, Hot tub & Fireplace
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.91 out of 5 average rating, 35 reviews