
Vacation rentals in Shelter Island
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Top-rated vacation rentals in Shelter Island
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Vacation rentals for every style
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Popular amenities for Shelter Island vacation rentals
Other great vacation rentals in Shelter Island

Apartment in Shelter Island Heights
5 out of 5 average rating, 7 reviewsCHIC WATER VIEW APT. ON SHELTER ISLAND
Guest favourite

Home in Shelter Island
5 out of 5 average rating, 13 reviewsWaterfront Treehouse with Pool as seen on HBO
Guest favourite

Home in North Fork
4.91 out of 5 average rating, 11 reviewsWaterfront home for design lovers
Top guest favourite

Home in Shelter Island
4.93 out of 5 average rating, 80 reviewsFamily Friendly Island Home
Guest favourite

Home in Shelter Island
4.92 out of 5 average rating, 38 reviewsLight, spacious 3bdr home steps to Wades Beach
Top guest favourite

Home in Shelter Island
5 out of 5 average rating, 9 reviews6-acre Hidden Estate for 10 w/FP, Pool, Chef's Kit
Guest favourite

Guesthouse in Shelter Island
4.9 out of 5 average rating, 10 reviewsStylish Studio Suite on Shelter Island
Guest favourite

Home in Shelter Island Heights
5 out of 5 average rating, 6 reviewsCharming Cottage on Shelter Island, Walk to Ferry
Quick stats about vacation rentals in Shelter Island
Total rentals
150 properties
Nightly prices starting at
$14 CAD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
50 properties have a pool
Destinations to explore
- The Hamptons Vacation rentals
- Long Island Vacation rentals
- Plainview Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Hudson Valley Vacation rentals
- Boston Vacation rentals
- Jersey Shore Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Pet-friendly rentals Shelter Island
- Kid-friendly rentals Shelter Island
- Rentals with pools Shelter Island
- Rentals with a firepit Shelter Island
- Rentals with a washer and dryer Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a hot tub Shelter Island
- Beachfront rentals Shelter Island
- Rentals with beach access Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with a patio Shelter Island
- House rentals Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with a fireplace Shelter Island
- Waterfront rentals Shelter Island
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Shinnecock Hills Golf Club
- Ocean Beach Park
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Silver Sands Beach
- Amagansett Beach
- Blue Shutters Beach
- Groton Long Point Main Beach
- Seaside Beach
- Ninigret Beach
- Sunken Meadow State Park
- Heckscher State Park
- Connetquot River State Park Preserve
- Outer Beach at Smith Point County Park