Book Holiday Homes in Shelter Island
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Featured Holiday Homes in Shelter Island

Quiet neighborhood, Family&Pet friendly, 5mins. from town & ocean beaches

Large Charming Historic House close to Beaches

Waterfront House with picture-perfect views from all 3 levels.

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Charming Village home in the heart of Southampton

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

10 Bedroom Hampton House with a regulation size Pickleball

Oceanfront Beach House lay in bed and hear the waves, boats , birds
Shelter Island Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Shelter Island vacation homes are the perfect way for you to wing it.
Holiday houses in Shelter Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Shelter Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Shelter Island adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shelter Island with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Shelter Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Shelter Island Holiday Homes essential information
Accommodation | 1627 Holiday Homes |
---|---|
Lowest Price | AU$186 |
Highest Price | AU$831 |
Popular accommodation | Quiet neighborhood, Family&Pet friendly, 5mins. from town & ocean beaches, Large Charming Historic House close to Beaches, Waterfront House with picture-perfect views from all 3 levels., Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included, Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi, Charming Village home in the heart of Southampton, Watermill Retreat, minutes from Southampton Town Ctr and Beaches!, 10 Bedroom Hampton House with a regulation size Pickleball, Oceanfront Beach House lay in bed and hear the waves, boats , birds |
Holiday Homes in Shelter Island
More accommodations in Shelter Island
Top trending hotels in Shelter Island

Montauk Manor

Gurney's Montauk Resort & Seawater Spa

Water's Edge Resort & Spa

Hyatt Place Long Island East End
More ways to explore Shelter Island
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^Subject to availability and chosen travel dates.