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Search results; Over 1,000 places in Shelter Island

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Guest favourite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
Hosted by Puja
11–16 Apr
4.97 out of 5 average rating, 189 reviews
Guest favourite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
Hosted by Julia
15–20 Apr
4.89 out of 5 average rating, 64 reviews
Home in Shelter Island
Hamptons - Shelter Island Farmhouse
Hosted by Jake
1–6 Apr
Guest favourite
Home in Shelter Island
CASA GYPSEA - a chic and peaceful 3 bedroom house
Hosted by a business
14–19 Apr
5.0 out of 5 average rating, 50 reviews
Guest favourite
Flat in Shelter Island Heights
Squire Chase House
Hosted by Jason
1–6 Apr
4.91 out of 5 average rating, 227 reviews
Guest favourite
Guest suite in Shelter Island
Private two-bedroom stay on Shelter Island
Hosted by Lily
26 Apr – 1 May
4.89 out of 5 average rating, 28 reviews
Guest favourite
Home in Shelter Island
Scandinavian family home on the water
Hosted by John
27 May – 1 Jun
4.93 out of 5 average rating, 15 reviews
Guest favourite
Guest house in Shelter Island
Sleek and Chic cottage/Pool House
Hosted by a business
1–6 Apr
5.0 out of 5 average rating, 25 reviews
Guest favourite
Guest house in Shelter Island
Lovely Island Cottage
Hosted by Lorin
1–6 Apr
4.95 out of 5 average rating, 22 reviews
Home in Shelter Island Heights
Laid Back Relaxation
Hosted by Jared
1–6 Apr
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Shelter Island
Shelter island retreat
Hosted by Alexis
1–6 Apr
4.97 out of 5 average rating, 156 reviews
Guest favourite
Villa in Shelter Island
The Lord‘s Villa & Estate
Hosted by Aimee
1–6 Apr
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Shelter Island
Beautiful beach home with pool & water views!
Hosted by Karen
1–6 Apr
4.92 out of 5 average rating, 52 reviews
Home in Shelter Island
Waterfront Haven
Hosted by Simon
1–8 Apr
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Shelter Island
Waterfront Treehouse with Pool as seen on HBO
Hosted by Jessica
4–9 Apr
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Shelter Island
Spacious house with pool.
Hosted by Maura
1–6 Apr
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Shelter Island
Sandpoint by Rove Travel | Modern 5BR w/ Pool
Hosted by Rove
1–6 Apr
New place to stay
Guest favourite
Cottage in Shelter Island
Shelter Island Waterfront Getaway
Hosted by Maureen
1–6 Apr
4.97 out of 5 average rating, 93 reviews