Search results; Over 1,000 places in Shelter Island

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Guest favorite
Cottage in Shelter Island
Shelter Island Waterfront Getaway
2 guests1 bedroom2 beds1 bath
May 3 – 8
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May 3 – 8
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ﺩ.ﺇ 9,191 for 5 nights
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
May 7 – 12
ﺩ.ﺇ 3,660 for 5 nights
for 5 nights
4.89 out of 5 average rating, 95 reviews
Home in Shelter Island
Waterfront Heavenly Hideaway with separate casa
6 beds
May 3 – 8
ﺩ.ﺇ 15,067 for 5 nights
for 5 nights
4.67 out of 5 average rating, 3 reviews
Guest favorite
Apartment in Shelter Island Heights
Squire Chase House
3 beds
May 3 – 8
ﺩ.ﺇ 14,315 for 5 nights
for 5 nights
4.91 out of 5 average rating, 245 reviews
Top guest favorite
Guest suite in Shelter Island
Chic and Cozy Suite with Private Entrance
1 bed
May 3 – 8
ﺩ.ﺇ 5,687 for 5 nights
for 5 nights
5.0 out of 5 average rating, 36 reviews
Top guest favorite
Guesthouse in Shelter Island
Bayfront 1BR/2BR detached guesthouse with pool
Free cancellation
Jun 21 – 28
ﺩ.ﺇ 11,946 for 7 nights
for 7 nights
5.0 out of 5 average rating, 64 reviews
Top guest favorite
Cottage in Shelter Island
3 Bedroom Cottage Gem
4 beds
May 3 – 8
ﺩ.ﺇ 11,472 for 5 nights
for 5 nights
4.96 out of 5 average rating, 105 reviews
Guest favorite
Home in Shelter Island
Scandinavian family home on the water
3 beds
May 27 – Jun 1
ﺩ.ﺇ 16,574 for 5 nights
for 5 nights
4.92 out of 5 average rating, 26 reviews
Home in Shelter Island
New vacation house on the island(new pool)
5 beds
May 3 – 8
ﺩ.ﺇ 17,004 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cottage in Shelter Island
Large Waterfront Cottage on Historic Estate
4 beds
May 17 – 22
ﺩ.ﺇ 8,395 for 5 nights
for 5 nights
4.78 out of 5 average rating, 55 reviews
Home in Shelter Island
Shelter Island 4 BR w Pool & Private Beach Access
6 beds
May 3 – 10
ﺩ.ﺇ 37,453 for 7 nights
for 7 nights
New place to stay
Guest favorite
Home in Shelter Island
Shelter island retreat
2 king beds
May 3 – 8
ﺩ.ﺇ 10,116 for 5 nights
for 5 nights
4.96 out of 5 average rating, 162 reviews
Superhost
Room in Shelter Island
Stay with Susan CReal estate broker,
Magnolia Cape with private entrance & private bath
May 3 – 8
ﺩ.ﺇ 4,951 for 5 nights
for 5 nights
4.71 out of 5 average rating, 21 reviews
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
6 beds
Sep 8 – 14
ﺩ.ﺇ 50,809 for 6 nights
for 6 nights
4.95 out of 5 average rating, 246 reviews
Top guest favorite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
3 beds
May 11 – 16
ﺩ.ﺇ 14,507 for 5 nights
for 5 nights
5.0 out of 5 average rating, 63 reviews
Guest favorite
Guesthouse in Shelter Island
Stylish Studio Suite on Shelter Island
1 bed
May 4 – 9
ﺩ.ﺇ 7,964 for 5 nights
for 5 nights
4.89 out of 5 average rating, 9 reviews
Top guest favorite
Cottage in Shelter Island
Waterfront Getaway on Shelter Island
3 beds
May 18 – 23
ﺩ.ﺇ 20,126 for 5 nights
for 5 nights
4.91 out of 5 average rating, 23 reviews
Superhost
Home in Shelter Island
There's a Beach Getaway!
4 beds
May 3 – 8
ﺩ.ﺇ 15,929 for 5 nights
for 5 nights
4.9 out of 5 average rating, 115 reviews
Top guest favorite
Cottage in Shelter Island
Shelter Island Cottage
6 beds
May 3 – 8
ﺩ.ﺇ 18,511 for 5 nights
for 5 nights
4.94 out of 5 average rating, 33 reviews