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

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

2 out of 5
Montauk
Located in Montauk, this vacation home is within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Quiet neighborhood, Family&Pet friendly, 5mins. from town & ocean beaches
Large Charming Historic House close to Beaches

Large Charming Historic House close to Beaches

Clinton
With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes ...
Large Charming Historic House close to Beaches
Waterfront House with picture-perfect views from all 3 levels.

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

Westbrook
Located in Westbrook (Westbrook Center), this vacation home is within a 5-minute drive of Westbrook Town Beach and Tanger Outlets.
Waterfront House with picture-perfect views from all 3 levels.
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Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

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

Clinton
When you stay at this vacation home in Clinton, you'll be near the beach and 11 minutes by foot from Clinton Town Beach.
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 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2 out of 5
Sag Harbor
With a stay at this vacation home in Sag Harbor, you'll be within a 15-minute walk of The Hamptons Beaches and Eastville Heritage House.
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
Charming Village home in the heart of Southampton

Charming Village home in the heart of Southampton

Southampton
With a stay at this vacation home in Southampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and North Main Street Historic ...
Charming Village home in the heart of Southampton
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

Watermill Retreat, minutes from Southampton Town Ctr and Beaches!

Water Mill
With a stay at this vacation home in Water Mill, you'll be within a 15-minute drive of The Hamptons Beaches and Parrish Art Museum.
Watermill Retreat, minutes from Southampton Town Ctr and Beaches!
10 Bedroom Hampton House with a regulation size Pickleball

10 Bedroom Hampton House with a regulation size Pickleball

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be near the beach, within a 5-minute drive of The Hamptons Beaches and Ponquogue Beach.
10 Bedroom Hampton House with a regulation size Pickleball
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Oceanfront Beach House lay in bed and hear the waves, boats , birds

Waterford
With a stay at this vacation home in Waterford, you'll be on the beach, within a 15-minute drive of Ocean Beach Park and Pleasure Beach.
Oceanfront Beach House lay in bed and hear the waves, boats , birds
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Top trending hotels in Shelter Island

Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AU$267 per night from 17 Mar to 18 Mar
AU$267
includes taxes & fees
17 Mar - 18 Mar
When you stay at Montauk Manor in Montauk, you'll be near the beach, within a 15-minute drive of The Hamptons Beaches and Montauk Point.
Montauk Manor
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway, Montauk, NY
The price is AU$831 per night from 16 Mar to 17 Mar
AU$831
includes taxes & fees
16 Mar - 17 Mar
Located in Montauk, Gurney's Montauk Resort & Seawater Spa is by the ocean, a 3-minute drive from Hither Hills State Park and 7 minutes from Shadmoor State ...
Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$337 per night from 30 Mar to 31 Mar
AU$337
includes taxes & fees
30 Mar - 31 Mar
With a stay at Water's Edge Resort & Spa in Westbrook (Westbrook Center), you'll be a 4-minute drive from Tanger Outlets and 8 minutes from Clinton Crossing ...
Water's Edge Resort & Spa
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Hyatt Place Long Island East End

Hyatt Place Long Island East End

3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 30 Mar to 31 Mar
AU$186
includes taxes & fees
30 Mar - 31 Mar
With a stay at Hyatt Place Long Island East End in Riverhead, you'll be on a river, just a 5-minute walk from Suffolk Theater and 6 minutes by foot from All ...
Hyatt Place Long Island East End
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See all available properties in Shelter Island
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.