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Airbnb, Vacation rentals and hotel deals in Shelter Island, NY

9.8 (44 reviews)
Peaceful and Private Shelter Island Getaway
Holiday home · 2 Guests · 1 Bedroom
$275 /night*
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9.6 (48 reviews)
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Holiday home · 2 Guests · 1 Bedroom
$450 /night*
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9.3 (3 reviews)
Arbor View House Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$394 /night
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10 (8 reviews)
Shelter Island Hidden Waterfront Gem
Holiday home · 2 Guests · 1 Bedroom
$500 /night*
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9.6 (36 reviews)
COTTAGE IS AVAILABLE FOR MONTHY, WEEKLY, WEEKENDS,Also WINTERS
Cottage · 2 Guests · 1 Bedroom
$500 /night*
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Cozy family cottage on Shelter Island
Holiday home · 2 Guests · 1 Bedroom
$425 /night*
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8.6 (3 reviews)
Rams Head Inn
Hotel · 2 Guests · 1 Bedroom
$221 /night
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9.7 (39 reviews)
The Menhaden Hotel
Hotel · 2 Guests · 1 Bedroom
$336 /night
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6.0 (1 review)
Beautiful Soundfront condominium
Condo · 2 Guests · 1 Bedroom
$750 /night*
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10 (34 reviews)
Sag Harbor Village Gem
Holiday home · 2 Guests · 1 Bedroom
$495 /night*
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9.8 (69 reviews)
'The Gate House' on Beach front Estate Walk to Village
Cottage · 2 Guests · 1 Bedroom
$250 /night*
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10 (2 reviews)
Chic Shelter Island Home, Pool and Gardens
Holiday home · 2 Guests · 1 Bedroom
$1,500 /night*
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8.7 (9 reviews)
The Shoals Suites & Slips
Hotel · 2 Guests · 1 Bedroom
$362 /night
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Southampton Stunner: Modern & Bright, Pool, Beach & More!
Holiday home · 2 Guests · 1 Bedroom
$950 /night*
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9.8 (79 reviews)
Waterfront Home, Dock, Kayak, Peloton, Paddleboards, HotTub, Pool, Strong WIFI
Holiday home · 2 Guests · 1 Bedroom
$1,283 /night*
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9.8 (59 reviews)
Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board
Cottage · 2 Guests · 1 Bedroom
$300 /night*
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Rosemorran Retreat
Holiday home · 2 Guests · 1 Bedroom
$997 /night
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9.8 (48 reviews)
Beautiful Renovated Beachfront Home
Holiday home · 2 Guests · 1 Bedroom
$650 /night*
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10 (29 reviews)
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
Holiday home · 2 Guests · 1 Bedroom
$1,032 /night*
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8.0 (184 reviews)
Sound View Greenport
Hotel · 2 Guests · 1 Bedroom
$201 /night
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Airbnb, Holiday Beachfront House with Air Conditioning in Shelter Island, NY

9.0 (28 reviews)
House on Chase Creek
B & B · 2 Guests · 1 Bedroom
$166 /night
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9.3 (3 reviews)
Arbor View House Bed and Breakfast
B & B · 2 Guests · 1 Bedroom
$394 /night
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9.8 (8 reviews)
The Stirling House Waterfront Inn Greenport
B & B · 2 Guests · 1 Bedroom
$316 /night
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How Does The Amenity Info Looks Like at Shelter Island, NY?
Shelter Island, NY Rental Amenities
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Check above for the most common and the least popular rental amenities in Shelter Island, and pick the one that fits your preference easily. In Shelter Island, 2788 rentals offer Internet or Wifi, 2690 rentals offer Air Conditioning, 2606 rentals offer Parking Available. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Hot Tub, Pets Friendly.
Which Price Range Is Considered As A Good Deal in Shelter Island, NY Area?
Vacation House & Cottage Rental Price Information in Shelter Island, NY
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The graph shows the percentages of vacation homes in each price bucket. Shelter Island has the largest percentage (55.68%) of homes in $500+ price range.
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Which Accommodations Should I Pick in Shelter Island, NY?
Rental Accommodation Info in Shelter Island, NY
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Before visiting Shelter Island, it is a good idea to explore all the accommodation types in this area, and pick the one that fits your group well. All the available accommodation types are: House, Cottage, Apartment, Condo, Estate, Farmhouse, Chateau / Country House, Bungalow, Townhome, Studio, Villa, Resort, Barn, Hotel, Guest House, Bed And Breakfast, Yacht, Chalet, Mobile Home, Cabin, Lodge. House is the most-liked rental type, with the largest percentage of 83.89%. The biggest home in this area available for rent is around 20000 square feet.The least popular accommodation in Shelter Island is Cabin rentals
How Many Accommodations Are Pets Allowed in Shelter Island, NY?
Percentage of Pet Friendly Rental Properties in Shelter Island, NY
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34.65% of vacation homes in Shelter Island are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Must-Visit Trails in Shelter Island, NY?
Best Trails In Shelter Island, NY
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Here are the trails we recommend in Shelter Island: Cedar Point, Long Pond Greenbelt Trail, Morton National Wildlife Trail, Mashomack Preserve, Southold Bayview Trail, Hashamomuck Pond, Sound View Dunes Park Forest Trail, Horton Point Lighthouse, Arshamomaque Preserve Trails, Dam Pond Trail.
Where Are The Campgrounds in Shelter Island, NY Area?
Most Visited Campgrounds In Shelter Island, NY
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If you love outdoors or travel with an RV, here are the campgrounds in Shelter Island: Niantic / I-95 Exit 72 KOA, Mystic KOA, Salem Farms Campground, Sunfox Campground, Grandview Camping Resort, Wolf's Den Family Campground, Odetah Camping Resort, Acorn Acres Campground, Little City Campground, Markham Meadows Campground.
What are the Airports in Shelter Island, NY?
Suggested Airports in Shelter Island, NY
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Here are the airports that located near Shelter Island:

Airbnb, Holiday Beachfront House with Fireplace in Shelter Island, NY

10 (157 reviews)
Southold Waterfront complete with Boat Dock, Boat Ramp, Hot Tub & Beaches
Holiday home · 2 Guests · 1 Bedroom
$800 /night*
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10 (2 reviews)
Chic Shelter Island Home, Pool and Gardens
Holiday home · 2 Guests · 1 Bedroom
$1,500 /night*
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10 (3 reviews)
Gorgeous Four Bedroom Home in Sag Harbor with Pool/water access
Holiday home · 2 Guests · 1 Bedroom
$700 /night*
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Airbnb, Vacation Cottage with Full Kitchen, and Other Rental Options in Shelter Island, NY

Spectacular 5 acre secluded private gem
Chalet · 2 Guests · 1 Bedroom
$2,000 /night*
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9.6 (122 reviews)
Quaint Cottage Close to LI Sound
Cottage · 2 Guests · 1 Bedroom
$200 /night*
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9.6 (36 reviews)
COTTAGE IS AVAILABLE FOR MONTHY, WEEKLY, WEEKENDS,Also WINTERS
Cottage · 2 Guests · 1 Bedroom
$500 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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