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300+ stays

Stays in Shelter Island

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SUPERHOST
Entire house in Sag Harbor
Sag Harbor Cottage, Walk to the Beach!
6 guests3 bedrooms3 beds1 bath
Air conditioningWifiKitchen
Rating 4.97 out of 5;111 reviews
Price:$580 / night
SUPERHOST
Private room in Sag Harbor
Sunset in village + standup board + bike + Kayak
2 guests1 bedroom1 bed1 private bath
Air conditioningWifi
Rating 4.92 out of 5;300 reviews
Price:$287 / night
SUPERHOST
Entire guest suite in Cutchogue
Walk to Vineyards, Beaches, Farms & Town
2 guests1 bedroom1 bed1 bath
Air conditioningWifiKitchen
Rating 4.89 out of 5;249 reviews
Price:$192 / night
SUPERHOST
Entire house in Sag Harbor
New! Hamptons Sag Harbor Village Pool& Beach House
8 guests4 bedrooms6 beds2 baths
PoolAir conditioningWifiKitchen
Rating 4.88 out of 5;66 reviews
Price:$1,071 / night
SUPERHOST
Private room in Sag Harbor
Queen Room in village + bike + kayak
2 guests1 bedroom2 beds1 private bath
Air conditioningWifi
Rating 4.89 out of 5;311 reviews
Price:$281 / night
SUPERHOST
Entire villa in East Hampton
Luxury STEPS from East Hampton Village!
6 guests4 bedrooms4 beds5.5 baths
PoolAir conditioningWifiKitchen
Rating 4.77 out of 5;31 reviews
Price:$1,456 / night
SUPERHOST
Entire house in Shelter Island
Case-Jennings House on Shelter Island 20-B-0001
4 guests2 bedrooms2 beds1 bath
Air conditioningWifiKitchen
Rating 5.0 out of 5;136 reviews
Price:$260 / night
SUPERHOST
Entire cottage in East Hampton
Carriage House - Cottage in East Hampton Village
4 guests1 bedroom3 beds1.5 baths
Air conditioningWifiKitchen
Rating 5.0 out of 5;59 reviews
Price:$299 / night
SUPERHOST
Entire house in Greenport
Nofo Bungalow-In The Heart of Greenport Village
6 guests2 bedrooms5 beds2 baths
Air conditioningWifiKitchen
Rating 4.97 out of 5;104 reviews
Price:$513 / night
SUPERHOST
Entire house in Greenport
Walk to it all! - Eat, Drink, Beach, Shop - Apt #2
6 guests2 bedrooms3 beds1 bath
Air conditioningWifiKitchen
Rating 4.95 out of 5;118 reviews
Price:$500 / night
SUPERHOST
Entire house in Southampton
This House is totally sanitized after every guest
8 guests4 bedrooms5 beds2 baths
PoolAir conditioningWifiKitchen
Rating 4.99 out of 5;73 reviews
Price:$695 / night
SUPERHOST
Entire house in East Hampton
Ritz-East Hampton Cottage- 5 stars
4 guests2 bedrooms3 beds2 baths
Air conditioningWifiKitchen
Rating 4.95 out of 5;127 reviews
Price:$529 / night
SUPERHOST
Entire house in East Hampton
East Hampton Safe Haven from New York City
12 guests5 bedrooms7 beds3.5 baths
PoolAir conditioningWifiKitchen
Rating 4.88 out of 5;58 reviews
Price:$1,000 / night
SUPERHOST
Entire guesthouse in Sag Harbor
Cottage in the Hamptons/Sag Harbor
2 guests1 bedroom1 bed1 bath
PoolAir conditioningWifiKitchen
Rating 4.97 out of 5;107 reviews
Price:$202 / night
Entire cottage in Southampton
Beautiful beachy Southampton cottage
3 guests1 bedroom1 bed1 bath
Air conditioningWifiKitchen
Rating 4.88 out of 5;67 reviews
Price:$314 / night
SUPERHOST
Entire cottage in East Hampton
Hamptons Styled Beach Cottage
6 guests3 bedrooms6 beds1.5 baths
Air conditioningWifiKitchen
Rating 4.89 out of 5;18 reviews
Price:$400 / night
SUPERHOST
Entire apartment in Sag Harbor
Village studio walk to havens beach and village
2 guestsStudio1 bed1 bath
Air conditioningWifiKitchen
Rating 4.87 out of 5;86 reviews
Price:$166 / night
SUPERHOST
Entire guest suite in Greenport
Village suite w/private entry near the beach
2 guests1 bedroom1 bed1 bath
Air conditioningWifi
Rating 4.93 out of 5;108 reviews
Price:$221 / night
SUPERHOST
Entire house in Shelter Island
The Lord‘s Cottage on the Water
4 guests2 bedrooms3 beds2 baths
Air conditioningWifiKitchen
Rating 4.85 out of 5;46 reviews
Price:$422 / night
SUPERHOST
Entire guesthouse in Southampton
Wonderful Private Spacious Pool House
6 guestsStudio5 beds1 bath
PoolAir conditioningWifiKitchen
Rating 4.97 out of 5;34 reviews
Price:$429 / night
1 20 of 300+ places to stay
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