Skip to content
300+ stays

Stays in Shelter Island

Showing you results for "Shelter Island, NY"
Review COVID-19 travel restrictions before you book.
Learn more
Entire house in Shelter Island
Luxurious 'Shelter Island Hideaway' w/ Pool!
10 guests4 bedrooms5 beds4 baths
WifiAir conditioningPoolKitchen
Price:$538 / night
Entire house in Peconic
Grand Family Home
14 guests5 bedrooms7 beds3.5 baths
WifiAir conditioningPoolKitchen
Price:$461 / night
SUPERHOST
Entire house in Shelter Island
Huge Island Getaway Pool HotTub By Beach
12 guests6 bedrooms7 beds5.5 baths
WifiAir conditioningPoolKitchen
Price:$546 / night
Entire house in East Hampton
3 Bed, 3 Bath House w Pool & Private Beach Access
7 guests3 bedrooms5 beds3 baths
WifiAir conditioningPoolKitchen
Price:$233 / night
Entire apartment in Sag Harbor
Artists Apartment & Guest Cabin.
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$123 / night
SUPERHOST
Entire house in Greenport
Nofo Bungalow-In The Heart of Greenport Village
6 guests2 bedrooms5 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$299 / night
SUPERHOST
Entire house in Shelter Island
George's Studio 20-B-0001
4 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Price:$289 / night
SUPERHOST
Entire apartment in Shelter Island Heights
Squire Chase House
6 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$350 / night
SUPERHOST
Entire house in East Hampton
NEW! Styled East Hampton: Private Clearwater Beach
8 guests3 bedrooms4 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$200 / night
Entire house in Shelter Island Heights
Renovated Victorian in the heart of it all
8 guests3 bedrooms4 beds3 baths
WifiAir conditioningKitchenFree parking
Price:$325 / night
SUPERHOST
Entire house in Shelter Island
Case-Jennings House on Shelter Island 20-B-0001
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$280 / night
Entire house in Southampton
Private 3.8 Acres with gunite pool
8 guests3 bedrooms5 beds2 baths
WifiAir conditioningPoolKitchen
Price:$195 / night
Entire cottage in New Suffolk
Mermaid cottage
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$125 / night
Entire cottage in Shelter Island
Large Waterfront Cottage on Private Estate
6 guests3 bedrooms4 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$275 / night
SUPERHOST
Entire apartment in Bridgehampton
Winter in the Hamptons
2 guestsStudio1 bed1 bath
WifiAir conditioningPoolFree parking
Price:$281 / night
Tiny house in Bridgehampton
Bridgehampton Private Loft Walk to Town Monthly
2 guestsStudio1 bed1 bath
WifiAir conditioningPoolFree parking
Price:$65 / night
Farm stay in Cutchogue
Farm House
4 guests2 bedrooms3 beds1.5 baths
WifiAir conditioningKitchenFree parking
Price:$105 / night
Entire apartment in Mattituck
Berry Flower Farm 2
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Price:$103 / night
SUPERHOST
Entire house in Southampton
Fantastic 3 Bedroom 2.5 Bath Home w Heated Pool
8 guests4 bedrooms5 beds2.5 baths
WifiAir conditioningPoolKitchen
Price:$183 / night
Entire apartment in Mattituck
Berry Flower Farm 1
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$89 / night
234515
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.