Search results; Over 1,000 homes in Shelter Island

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Guest favorite
Home in Shelter Island
Cozy 3BR Shelter Island Escape Near Beach
6 guests3 bedrooms4 beds1 bath
Sep 7 – 12
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Sep 7 – 12
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ﺩ.ﺇ16,144 for 5 nights

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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, 116 reviews
Home in Shelter Island
Mid-Century Gem with Pool. Steps to Beach.
3 beds
Sep 3 – 10
ﺩ.ﺇ19,508 for 7 nights
New place to stay
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, 141 reviews
Guest favorite
Home in Shelter Island
Waterfront Heavenly Hideaway with separate casa
6 beds
Sep 21 – 26
ﺩ.ﺇ20,018 for 5 nights
4.89 out of 5 average rating, 9 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
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, 157 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
Room in Shelter Island Heights
Stay with BethHospitality,
SEVEN on Shelter - Luxury King Guest Room
Sep 1 – 6
ﺩ.ﺇ9,971 for 5 nights
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, 111 reviews
Guest favorite
Home in Shelter Island
Shelter island retreat
2 king beds
Sep 21 – 26
ﺩ.ﺇ10,117 for 5 nights
4.96 out of 5 average rating, 168 reviews
Home in Shelter Island
Cottage on the lake!
6 beds
Sep 7 – 12
ﺩ.ﺇ11,236 for 5 nights
New place to stay
Superhost
Home in Shelter Island
Waterfront shelter island gem
5 beds
Sep 7 – 12
ﺩ.ﺇ12,033 for 5 nights
4.96 out of 5 average rating, 23 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, 253 reviews
Home in Southampton
Lovely Sanctuary in Southampton
3 beds
Sep 5 – 10
ﺩ.ﺇ16,708 for 5 nights
New place to stay
Guest favorite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
4 beds
Sep 1 – 6
ﺩ.ﺇ27,638 for 5 nights
5.0 out of 5 average rating, 13 reviews
Guest favorite
Home in Shelter Island
Moonlit Manor | Shelter Island Escape w/ NEW Sauna
3 beds
Sep 3 – 8
ﺩ.ﺇ7,642 for 5 nights
4.93 out of 5 average rating, 15 reviews
Guesthouse in Shelter Island
Modern Waterfront Cottage Oasis
2 beds
Sep 1 – 6
ﺩ.ﺇ20,449 for 5 nights
Top guest favorite
Home in Shelter Island
Chic, serene, designer home with pool and views
5 beds
Sep 8 – 13
ﺩ.ﺇ26,265 for 5 nights
4.98 out of 5 average rating, 41 reviews