Holiday houses in Shelter Island
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Top-rated holiday rentals in Shelter Island
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island holiday rentals
Other great holiday rentals in Shelter Island
Guest favourite
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
7–14 Oct
$1,229 NZD per night
Guest favourite
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
10–17 Jul
$1,281 NZD per night
Guest favourite
Guest suite in Southold
4.94 out of 5 average rating, 97 reviewsComfortable Suite, a walk to the beach
22–29 Mar
$275 NZD per night
Superhost
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
7–14 Nov
$584 NZD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
14–21 Sep
$1,525 NZD per night
Guest favourite
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
19–26 Nov
$1,266 NZD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
12–19 Mar
$2,037 NZD per night
Guest favourite
Home in Greenport
5.0 out of 5 average rating, 10 reviewsThe Sandy Shack - Coastal Escape
20–27 Oct
$1,150 NZD per night
Quick stats about holiday rentals in Shelter Island
Total rentals
140 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$203 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
- Long Island Holiday rentals
- Martha's Vineyard Holiday rentals
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- Montauk Holiday rentals
- Hoboken Holiday rentals
- Washington Holiday rentals
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- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Fitness-friendly rentals Shelter Island
- Rentals with a fireplace Shelter Island
- Rentals with pools Shelter Island
- Beachfront rentals Shelter Island
- Rentals with outdoor seating Shelter Island
- Kid-friendly rentals Shelter Island
- Rentals with a patio Shelter Island
- Rentals with a washing machine and dryer Shelter Island
- Family-friendly rentals Shelter Island
- Rentals with a fire pit Shelter Island
- Pet-friendly rentals Shelter Island
- House rentals Shelter Island
- Monthly Rentals Shelter Island
- Rentals with beach access Shelter Island
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