Search results; Over 1,000 homes in Shelter Island

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Home in Shelter Island
Shelter island retreat
5 guests2 bedrooms2 beds1 bath
Sep 21 – 26
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Sep 21 – 26
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ﺩ.ﺇ10,117 for 5 nights

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Home in Shelter Island
Mid-Century Gem with Pool. Steps to Private Beach.
3 beds
Sep 3 – 10
ﺩ.ﺇ20,369 for 7 nights
New place to stay
Guest favorite
Home in Shelter Island
Waterfront Heavenly Hideaway with separate casa
6 beds
Sep 7 – 12
ﺩ.ﺇ20,018 for 5 nights
4.89 out of 5 average rating, 9 reviews
Guest favorite
Room in Shelter Island
Stay with SharonHosting for 8 years,
Sunny Country cottage with pool
Sep 1 – 6
ﺩ.ﺇ5,102 for 5 nights
4.94 out of 5 average rating, 142 reviews
Top guest favorite
Room in Shelter Island
Stay with JimboMath teacher @ sihs,
Master Suite at RedHouse
Sep 8 – 13
ﺩ.ﺇ3,543 for 5 nights
4.94 out of 5 average rating, 158 reviews
Guest favorite
Room in Shelter Island
Stay with Rosemary KHosting for 4 years,
Grace House
Sep 6 – 11
ﺩ.ﺇ6,049 for 5 nights
5.0 out of 5 average rating, 41 reviews
Top guest favorite
Guesthouse in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
2 beds
Sep 7 – 12
ﺩ.ﺇ8,718 for 5 nights
4.99 out of 5 average rating, 71 reviews
Guest favorite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
Sep 22 – 27
ﺩ.ﺇ3,584 for 5 nights
4.91 out of 5 average rating, 117 reviews
Top guest favorite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4 beds
Sep 1 – 6
ﺩ.ﺇ12,549 for 5 nights
4.96 out of 5 average rating, 112 reviews
Guest favorite
Cottage in Shelter Island
Shelter Island Cottage
6 beds
Sep 15 – 20
ﺩ.ﺇ29,274 for 5 nights
4.94 out of 5 average rating, 33 reviews
Guest favorite
Room in Shelter Island
Stay with Susan CReal estate broker,
Magnolia Cape with private entrance & private bath
Sep 13 – 18
ﺩ.ﺇ4,951 for 5 nights
4.78 out of 5 average rating, 32 reviews
Home in Shelter Island
Cottage on the lake!
6 beds
Sep 7 – 12
ﺩ.ﺇ10,068 for 5 nights
New place to stay
Top guest favorite
Home in Shelter Island
Hamptons - Shelter Island Farmhouse
4 beds
Sep 29 – Oct 4
ﺩ.ﺇ9,945 for 5 nights
4.97 out of 5 average rating, 31 reviews
Guest favorite
Apartment in Shelter Island Heights
Squire Chase House
3 beds
Sep 14 – 19
ﺩ.ﺇ14,314 for 5 nights
4.91 out of 5 average rating, 254 reviews
Top guest favorite
Home in Shelter Island Heights
Laid Back Relaxation
4 beds
Sep 8 – 13
ﺩ.ﺇ12,821 for 5 nights
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Shelter Island
Scandinavian family home on the water
1 bed
Sep 19 – 24
ﺩ.ﺇ17,435 for 5 nights
4.94 out of 5 average rating, 34 reviews
Guesthouse in Shelter Island
Modern Waterfront Cottage Oasis
2 beds
Sep 1 – 6
ﺩ.ﺇ20,449 for 5 nights
Top guest favorite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bed
Sep 1 – 6
ﺩ.ﺇ5,752 for 5 nights
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
6 beds
Sep 28 – Oct 3
ﺩ.ﺇ22,072 for 5 nights
4.95 out of 5 average rating, 255 reviews