300+ stays

Stays in Shelter Island

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Entire house in Shelter Island
Luxurious 'Shelter Island Hideaway' w/ Pool!
10 guests4 bedrooms5 beds4 baths
WifiAir conditioningPoolKitchen
Price:$538 / night
SUPERHOST
Entire house in Shelter Island
Huge Island Getaway Pool HotTub By Beach
12 guests6 bedrooms7 beds5.5 baths
WifiAir conditioningPoolKitchen
Price:$612 / night
Entire house in Sag Harbor
Secret Healing Oasis with Indoor Pool
5 guests2 bedrooms2 beds1 bath
WifiAir conditioningPoolKitchen
Price:$793 / night
Entire house in Laurel
Waterfront Retreat on Peconic Bay
8 guests4 bedrooms4 beds3 baths
WifiAir conditioningKitchenFree parking
Price:$806 / 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 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 Shelter Island
Peaceful Retreat: Gourmet kitchen & fireplace!
6 guests5 bedrooms10 beds3.5 baths
WifiAir conditioningPoolKitchen
Price:$511 / 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
LUXE
Entire villa in Sag Harbor
Deerfield Delight
14 guests7 bedrooms9 beds5 baths
PoolSonos sound systemSun loungersGated property
Price:$600 / night
SUPERHOST
Entire villa in Shelter Island
The Lord‘s Villa & Estate
8 guests4 bedrooms4 beds3 baths
WifiAir conditioningKitchenFree parking
Price:$699 / 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 East Hampton
NEW! Styled East Hampton: Private Clearwater Beach
8 guests3 bedrooms4 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$129 / 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 cottage in Shelter Island
Shelter Island Waterfront Getaway
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Price:$350 / night
SUPERHOST
Entire house in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
6 guests3 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$346 / night
Entire house in Southold
Beautiful BEACHFRONT Family Home with huge yard!!
8 guests3 bedrooms5 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$299 / night
SUPERHOST
Entire house in East Hampton
Light-filled, modern home near Bay & Ocean
6 guests4 bedrooms5 beds2 baths
WifiAir conditioningPoolKitchen
Price:$271 / night
SUPERHOST
Entire cottage in Southold
Sweet Southold Charmer
4 guests2 bedrooms0 beds1 bath
WifiAir conditioningKitchenFree parking
Price:$344 / night
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1 – 20 of 300+ places to stay
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