300+ stays

Stays in Shelter Island

More than 1,900 guests have stayed in Shelter Island.
On average they rated their stays 4.9 out of 5 stars.
SUPERHOST
Entire rental unit in Shelter Island Heights
Squire Chase House
6 guests3 bedrooms3 beds2 baths
WifiKitchen
$371 per night
SUPERHOST
Entire residential home in Shelter Island
George's Studio 20-B-0001
4 guests2 bedrooms2 beds1.5 baths
WifiKitchen
$375 per night
Entire cottage in Shelter Island
Waterfront Cottage on Private Estate
4 guests1 bedroom2 beds1 bath
WifiKitchen
$305 per night
SUPERHOST
Entire residential home in Shelter Island
Case-Jennings House on Shelter Island 20-B-0001
4 guests2 bedrooms2 beds1 bath
WifiKitchen
$350 per night
SUPERHOST
Entire cottage in Shelter Island
Shelter Island Waterfront Getaway
2 guests1 bedroom2 beds1 bath
WifiKitchen
$375 per night
Entire rental unit in Shelter Island
Modern Waterview Apartment in Silver Beach
2 guests1 bedroom1 bed1 bath
WifiKitchen
$300 per night
SUPERHOST
Entire guesthouse in Shelter Island
Waterfront carriage house studio
4 guests1 bedroom2 beds1 bath
PoolWifiKitchen
$364 per night
Entire rental unit in Shelter Island Heights
CHIC WATER-VIEW APT W POOL, TENNIS, FREE PARKING
3 guests1 bedroom2 beds1 bath
PoolWifiKitchen
$400 per night
SUPERHOST
Entire residential home in Shelter Island
SHELTER ISLAND House w Pool peaceful 2+ acres
6 guests3 bedrooms4 beds2 baths
PoolWifiKitchen
$700 per night
Entire residential home in Shelter Island
Secluded Shelter Island cottage
5 guests3 bedrooms5 beds1.5 baths
WifiKitchen
$318 per night
Entire cottage in Shelter Island
Classic Shelter Is. 2 bedroom residential home
4 guests2 bedrooms2 beds2 baths
WifiKitchen
$299 per night
Entire residential home in Shelter Island
ISLAND RETREAT Newly renovated 5 bedrooms Sleeps 8
8 guests5 bedrooms5 beds2 baths
WifiKitchen
$450 per night
SUPERHOST
Entire guesthouse in Shelter Island
Sleek and Chic cottage/Pool House
2 guestsStudio1 bed1 bath
PoolWifiKitchen
$145 per night
SUPERHOST
Entire guest suite in Shelter Island
Charming & Elegant Shelter Island Suite
2 guests1 bedroom1 bed1 bath
Wifi
$299 per night
Entire residential home in Shelter Island
Full waterviews, steps to the beach, kayaks available
6 guests4 bedrooms6 beds2 baths
WifiKitchen
$378 per night
Entire cottage in Shelter Island
Cozy Shelter Island 2 Bedroom 1 Bath Cottage
7 guests2 bedrooms5 beds1 bath
WifiKitchen
$407 per night
SUPERHOST
Entire guest suite in Greenport
Village suite w/private entry near the beach
2 guests1 bedroom1 bed1 bath
Wifi
$196 per night
SUPERHOST
Entire residential home in Shelter Island
Beautiful spacious home -heated pool & water views
6 guests5 bedrooms10 beds3.5 baths
PoolWifiKitchen
$706 per night
SUPERHOST
Entire residential home in Shelter Island
Spacious Shelter Island home near bay & beach
5 guests4 bedrooms5 beds2 baths
WifiKitchen
$350 per night
Entire guesthouse in Shelter Island
Lovely Island Cottage
2 guests1 bedroom1 bed1 bath
WifiKitchen
$400 per night
1 – 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.