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300+ stays

Stays in Shelter Island

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SUPERHOST
Entire apartment in Greenport
Harbor Front House II
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchen
Price:$100 / night
Entire house in Sag Harbor
New Listing: Head out East to this wooded oasis!
6 guests3 bedrooms3 beds2 baths
PoolWifiAir conditioning
Price:$4,672 / night
Entire apartment in Sag Harbor
Artists Apartment & Guest Cabin.
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchen
Rating 4.77 out of 5;101 reviews
Price:$128 / night
Entire house in East Hampton
3 Bed, 3 Bath House w Pool & Private Beach Access
7 guests3 bedrooms5 beds3 baths
PoolWifiAir conditioningKitchen
Rating 4.76 out of 5;46 reviews
Price:$242 / night
Entire house in Shelter Island
Shelter Island Sundrenched Retreat /walk to beach
6 guests3 bedrooms5 beds2 baths
WifiAir conditioningKitchen
Price:$222 / night
Entire house in Shelter Island
Luxurious 'Shelter Island Hideaway' w/ Pool!
10 guests4 bedrooms5 beds4 baths
PoolWifiAir conditioningKitchen
Rating 5.0 out of 5;5 reviews
Price:$528 / night
SUPERHOST
Entire apartment in Shelter Island Heights
Squire Chase House
6 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchen
Rating 4.92 out of 5;148 reviews
Price:$350 / night
SUPERHOST
Entire cottage in East Hampton
Carriage House - Cottage in East Hampton Village
4 guests1 bedroom3 beds1.5 baths
WifiAir conditioningKitchen
Rating 5.0 out of 5;68 reviews
Price:$199 / night
SUPERHOST
Entire guesthouse in Southampton
5 Star Rated Private Cottage Southampton/Sag Hrbr
2 guestsStudio2 beds1 bath
WifiAir conditioning
Rating 4.96 out of 5;56 reviews
Price:$271 / night
Entire cottage in Sag Harbor
Sag Harbor Water Sunsets & Easy Stroll to Village!
6 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchen
Rating 5.0 out of 5;9 reviews
Price:$477 / night
SUPERHOST
Entire house in Shelter Island
George's Studio 20-B-0001
4 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchen
Rating 5.0 out of 5;15 reviews
Price:$289 / night
SUPERHOST
Entire house in Shelter Island
Case-Jennings House on Shelter Island 20-B-0001
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchen
Rating 4.99 out of 5;143 reviews
Price:$282 / night
SUPERHOST
Entire house in Shelter Island
Huge Island Getaway Pool HotTub By Beach
12 guests6 bedrooms7 beds5.5 baths
PoolWifiAir conditioningKitchen
Rating 5.0 out of 5;24 reviews
Price:$852 / night
SUPERHOST
Entire cottage in Southold
Sweet Southold Charmer
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchen
Rating 4.91 out of 5;242 reviews
Price:$357 / night
SUPERHOST
Entire guest suite in Shelter Island
Studio sweet on Shelter Island
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchen
Rating 4.67 out of 5;12 reviews
Price:$175 / night
SUPERHOST
Entire cottage in Shelter Island
Shelter Island Waterfront Getaway
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchen
Rating 4.97 out of 5;36 reviews
Price:$350 / night
Entire cottage in Shelter Island
Romantic Shelter Island Cottage w/2 Pools & Pond
5 guests2 bedrooms3 beds2 baths
PoolWifiAir conditioningKitchen
Price:$507 / night
SUPERHOST
Entire apartment in Sag Harbor
Sunsets and Beach
2 guests1 bedroom4 beds1 bath
WifiAir conditioningKitchen
Rating 4.87 out of 5;126 reviews
Price:$182 / night
Entire cottage in New Suffolk
Mermaid cottage
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchen
Rating 4.75 out of 5;12 reviews
Price:$225 / night
SUPERHOST
Entire house in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
6 guests3 bedrooms3 beds1 bath
WifiAir conditioningKitchen
Rating 4.97 out of 5;118 reviews
Price:$377 / night
1 20 of 300+ places to stay
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