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

Room in Shelter Island Heights
SEVEN on Shelter - Queen Room w/Private Bathroom
1 bedroom, 1 bed, 1 shared bathroom
30 Aug – 4 Sept
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5.0 out of 5 average rating, 5 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
Charming Farmhouse with Pool
5.0 out of 5 average rating, 8 reviews, 6 bedrooms, 3 bathrooms
1–6 Aug
Top guest favourite
Home in Shelter Island
Family Friendly Island Home
4.93 out of 5 average rating, 84 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Cottage in Shelter Island
Shelter Island Cottage
4.95 out of 5 average rating, 41 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
Home in Shelter Island
Captain Don’s Paradise
4.92 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4.97 out of 5 average rating, 122 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
Home in Sag Harbor
Shelter Island Shell Beach Oasis
New place to stay, 4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 5 beds, 3 bathrooms
7–12 Aug
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Shelter Island
Shelter Island Retreat, 5 bdrms near everything!
5.0 out of 5 average rating, 24 reviews, 5 bedrooms, 5 beds, 2 bathrooms
23–30 Aug
Top guest favourite
Home in Shelter Island
Newly Renovated w/ Pool, Hot tub & Fireplace
4.91 out of 5 average rating, 35 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4.92 out of 5 average rating, 95 reviews, 4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
4.99 out of 5 average rating, 74 reviews, 1 bedroom, 2 beds, 1 bathroom
22–29 Aug
Top guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
4.92 out of 5 average rating, 142 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
4.96 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Aug
Guest favourite
Home in Shelter Island
Mid-Century Gem with Pool. Steps to Private Beach.
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
7–14 Sept
Top guest favourite
Guest suite in Greenport
Private Suite in a Greenport Historical Townhouse
4.97 out of 5 average rating, 121 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Room in Shelter Island
Master Suite at RedHouse
4.95 out of 5 average rating, 167 reviews, 1 king bed, 1 bathroom
21–26 Aug