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Search results; 179 places in Shelter Island

Flat in Shelter Island Heights
Shelter Island Waterview Villa
2 beds
20–25 Apr
New place to stay
Guest favourite
Flat in Shelter Island Heights
Squire Chase House
3 beds
20–25 Apr
4.91 out of 5 average rating, 227 reviews
Flat in Shelter Island
Modern Waterview Apartment in Silver Beach
1 queen bed
30 Aug – 4 Sep
5.0 out of 5 average rating, 14 reviews
Flat in Shelter Island
Private One Bedroom Apt
1 queen bed
20–25 Apr
New place to stay
Superhost
Flat in Sag Harbor
Well-appointed one bedroom Apt
2 beds
19–24 Apr
4.87 out of 5 average rating, 15 reviews
Guest favourite
Flat in Southold
Bright, Southold Studio Apt near beach & town
2 beds
28 Apr – 3 May
4.96 out of 5 average rating, 100 reviews
Guest favourite
Flat in Sag Harbor
Sag Harbor Village Oasis
1 king bed
21–26 Apr
4.88 out of 5 average rating, 133 reviews
Flat in Greenport
Harborview King with Balcony at Greenport
1 king bed
21–26 Apr
Guest favourite
Flat in Greenport
Quiet Neighborhood and only steps to Town
20–25 Apr
4.86 out of 5 average rating, 141 reviews
Flat in Sag Harbor
"Tranquil Sag Harbor Hideaway"
1 queen bed
28 Apr – 3 May
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Greenport
Lovely 2-bedroom apartment in a historic home
2 beds
29 Apr – 4 May
4.97 out of 5 average rating, 61 reviews
Guest favourite
Flat in Sag Harbor
Updated apartment in historic village home
2 beds
27 Apr – 2 May
4.98 out of 5 average rating, 131 reviews
Guest favourite
Flat in Sag Harbor
Pet friendly, artists apartment & guest cabin.
2 queen beds
26 Apr – 1 May
4.84 out of 5 average rating, 171 reviews
Guest favourite
Flat in Greenport
Greenport Village View - Walkable 2BR Stay
3 beds
30 Apr – 5 May
4.97 out of 5 average rating, 195 reviews
Guest favourite
Flat in Greenport
Vintage 1880 Victorian gem.
On Sandy Beach
21–26 Jul
4.96 out of 5 average rating, 24 reviews
Guest favourite
Flat in Greenport
Lovely 1st floor of farmhouse, wineries/downtown
19–24 Apr
4.9 out of 5 average rating, 29 reviews
Guest favourite
Room in Southold
Stay with RobertRetired,
Cozy guest room - quiet getaway - wine country
24–29 Jun
4.99 out of 5 average rating, 116 reviews
Guest favourite
Flat in Greenport
Farmhouse vibe in heart of Greenport
3 beds
20–25 Apr
4.95 out of 5 average rating, 20 reviews