Search results; Over 1,000 homes in Shelter Island

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Guest favorite
Home in Shelter Island
Shelter island retreat
5 guests2 bedrooms2 beds1 bath
Aug 16 – 21
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Aug 16 – 21
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ﺩ.ﺇ10,117 for 5 nights

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Guest favorite
Room in Shelter Island
Stay with Rosemary KHosting for 4 years,
Grace House
Aug 1 – 6
ﺩ.ﺇ6,339 for 5 nights
5.0 out of 5 average rating, 36 reviews
Guest favorite
Room in Shelter Island
Stay with Susan CReal estate broker,
Magnolia Cape with private entrance & private bath
Aug 3 – 8
ﺩ.ﺇ4,951 for 5 nights
4.76 out of 5 average rating, 25 reviews
Guest favorite
Home in Shelter Island
Waterfront Heavenly Hideaway with separate casa
Free cancellation
Aug 2 – 7
ﺩ.ﺇ44,771 for 5 nights
4.86 out of 5 average rating, 7 reviews
Guest favorite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
1 queen bed
Aug 9 – 14
ﺩ.ﺇ3,681 for 5 nights
4.9 out of 5 average rating, 106 reviews
Top guest favorite
Room in Shelter Island
Stay with JimboMath teacher @ sihs,
Master Suite at RedHouse
Aug 6 – 11
ﺩ.ﺇ4,370 for 5 nights
4.94 out of 5 average rating, 147 reviews
Guest favorite
Home in Shelter Island
There's a Beach Getaway!
Free cancellation
Aug 3 – 8
ﺩ.ﺇ18,081 for 5 nights
4.9 out of 5 average rating, 117 reviews
Guest favorite
Home in Shelter Island
Scandinavian family home on the water
1 bed
Aug 21 – 26
ﺩ.ﺇ35,516 for 5 nights
4.94 out of 5 average rating, 31 reviews
Guest favorite
Home in Shelter Island
Modern, spacious SI home with pool
5 beds
Aug 1 – 6
ﺩ.ﺇ24,366 for 5 nights
4.98 out of 5 average rating, 86 reviews
Guest favorite
Cottage in Shelter Island
Shelter Island Cottage
Free cancellation
Sep 15 – 20
ﺩ.ﺇ29,274 for 5 nights
4.94 out of 5 average rating, 33 reviews
Guest favorite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
Free cancellation
Sep 1 – 6
ﺩ.ﺇ5,752 for 5 nights
5.0 out of 5 average rating, 37 reviews
Home in Shelter Island
Shelter Island waterfront w/pool
Free cancellation
Aug 1 – 8
ﺩ.ﺇ39,928 for 7 nights
New place to stay
Room in Shelter Island
Stay with JaneHosting for 8 years,
Room in Charming Coastal Cottage
Sep 23 – 28
ﺩ.ﺇ3,380 for 5 nights
4.96 out of 5 average rating, 23 reviews
Room in Shelter Island Heights
Stay with BethHospitality,
SEVEN on Shelter - Queen Guest Room
Aug 4 – 9
ﺩ.ﺇ11,688 for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Shelter Island
Cottage on the lake!
6 beds
Aug 14 – 19
ﺩ.ﺇ9,423 for 5 nights
New place to stay
Superhost
Home in Shelter Island
Waterfront shelter island gem
5 beds
Aug 1 – 6
ﺩ.ﺇ28,822 for 5 nights
4.95 out of 5 average rating, 22 reviews
Top guest favorite
Cottage in Greenport
Coastal Cottage | Near Beach & Town | Baby Gear
Free cancellation
Aug 5 – 10
ﺩ.ﺇ13,858 for 5 nights
5.0 out of 5 average rating, 24 reviews
Guest favorite
Home in Shelter Island Heights
Silver Beach, 3 Bedroom cottage w/ pool
Free cancellation
Aug 31 – Sep 5
ﺩ.ﺇ13,346 for 5 nights
4.91 out of 5 average rating, 45 reviews
Guest favorite
Home in Shelter Island
New vacation house on the island with the pool
5 beds
Aug 31 – Sep 5
ﺩ.ﺇ29,231 for 5 nights
5.0 out of 5 average rating, 5 reviews