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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, 4 reviews
Home in Sag Harbor
Shelter Island Shell Beach Oasis
4 bedrooms, 5 beds, 3 bathrooms
3–8 Aug
New place to stay
Home in Shelter Island Heights
Creekside House Shelter Island
4 bedrooms, 5 beds, 3.5 bathrooms
5–11 Aug
Guest favourite
Home in Shelter Island
Charming Farmhouse with Pool
6 bedrooms, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 8 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, 40 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, 84 reviews
Top guest favourite
Home in Greenport
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.96 out of 5 average rating, 54 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, 122 reviews
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
Guest favourite
Home in Shelter Island
Peaceful Bright Country House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Shelter Island
New vacation house on the island with the pool
3 bedrooms, 5 beds, 3 bathrooms
1–6 Aug
5.0 out of 5 average rating, 8 reviews
Home in Shelter Island
Private Shelter Island Escape | Huge Yard + Pool
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 74 reviews
Guest favourite
Home in Shelter Island Heights
Silver Beach, 3 Bedroom cottage w/ pool
3 bedrooms, 4 beds, 2 bathrooms
4–9 Sept
4.91 out of 5 average rating, 53 reviews
Top guest favourite
Home in Shelter Island
Surf Scoter Cottage Shelter Island
4 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
4.91 out of 5 average rating, 94 reviews
Guest favourite
Home in Greenport
The Greenport Bungalow
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 294 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
4.92 out of 5 average rating, 142 reviews
Guest favourite
Home in Greenport
Bayview house with salt water pool & private chef
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.85 out of 5 average rating, 13 reviews
Top guest favourite
Home in Sag Harbor
Sag Harbor Summer House
3 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 8 reviews