Search results; Over 1,000 places

Display total before taxes
Guest favorite
Home in Shelter Island
Light, spacious 3bdr home steps to Wades Beach
1 min walk
Apr 30 – May 5
$500 per night
4.92 out of 5 average rating, 36 reviews
Guest favorite
Home in Shelter Island
Shelter island retreat
5 min walk
Apr 30 – May 5
$450 per night
4.96 out of 5 average rating, 162 reviews
Guest favorite
Home in Shelter Island
Huge Island Getaway Pool HotTub Walk To Beach
10 min drive
Apr 20 – 25
$480 per night, originally $995
4.95 out of 5 average rating, 244 reviews
Guest favorite
Place to stay in Shelter Island
Casual Island Getaway - Walk to the Beach
10 min drive
Apr 17 – 22
$195 per night
4.89 out of 5 average rating, 95 reviews
Guest favorite
Home in Shelter Island
Beautiful Home on Shelter Island
11 min walk
Apr 21 – 26
$630 per night
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Shelter Island
All Seasons Rental
10 min drive
Apr 22 – 27
$150 per night
4.72 out of 5 average rating, 39 reviews
Top guest favorite
Home in Greenport
Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)
20 min drive
May 4 – 9
$105 per night, originally $217
4.93 out of 5 average rating, 463 reviews
Guest favorite
Home in Shelter Island
Stunning water views, huge pool, family resort
1 min walk
Apr 18 – 24
$800 per night
4.92 out of 5 average rating, 51 reviews
Top guest favorite
Cottage in Shelter Island
3 Bedroom Cottage Gem
10 min drive
Apr 20 – 25
$475 per night
4.96 out of 5 average rating, 105 reviews
Guest favorite
Home in Shelter Island
Scandinavian family home on the water
13 min walk
May 27 – Jun 1
$800 per night
4.92 out of 5 average rating, 26 reviews
Guest favorite
Condo in Greenport
Beachside Waterview 2Br Condo w/ Pool in Greenport
20 min drive
Apr 20 – 25
$140 per night
4.92 out of 5 average rating, 137 reviews
Top guest favorite
Home in Shelter Island
Hamptons - Shelter Island Farmhouse
10 min drive
May 27 – Jun 1
$630 per night
5.0 out of 5 average rating, 22 reviews
Guest favorite
Home in Shelter Island
All season island beach oasis - Hamptons area!
10 min drive
Apr 20 – 25
$400 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Shelter Island
Beautiful beach home with pool & water views!
10 min drive
Apr 17 – 22
$572 per night, originally $635
4.93 out of 5 average rating, 59 reviews
Top guest favorite
Room in Shelter Island
Master Suite at RedHouse
10 min drive
Apr 27 – May 2
$135 per night
4.93 out of 5 average rating, 138 reviews
Cottage in Greenport
Coastal Cottage | 3-Min Walk to Beach, Near Town
20 min drive
May 2 – 7
$359 per night
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Home in Sag Harbor
Beach Cottage | Steps to Water | Firepit
20 min drive
May 1 – 6
$284 per night
5.0 out of 5 average rating, 15 reviews
Top guest favorite
Villa in Shelter Island
The Lord‘s Villa & Estate
10 min drive
Apr 22 – 27
$1,159 per night
5.0 out of 5 average rating, 19 reviews