Book Luxury Summer Rentals in Shelter Island

We selected the 930 homes worth renting in this location

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Home spotlights in Shelter Island

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

The Striped Sea Bass

The Striped Sea Bass

  • 6 guests

  • 3 bedrooms

Bay Point, Noyack

If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.


We selected the top 3% holiday homes in Shelter Island Vacation Rentals for Summer

Explore the 930 most perfect homes in our collection

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Most popular homes in Shelter Island

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

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Check upcoming rates & availability for Shelter Island Vacation Rentals for Summer


Frequently asked questions

Explore our remarkable range of luxury Summer Rentals in Shelter Island. There's no time for average stays, so treat yourself to a stay in one of the most impressive rentals around. Each and every home in our selection is put through numerous rounds of thorough testing, with everything from shower pressure to a home's design being closely checked for quality. Only the finest 3% of homes are awarded the prestigious Plum Award, so you can book with total confidence. Rentals in our range come fully furnished, with a well-equipped kitchen, essential bathroom toiletries, and all linen included to make you feel right at home. Book a memorable trip to an unforgettable Vacation Rental for Summer in Shelter Island today, and make the most of the year's warmest season. If you require any assistance, call on the help of our experts - they're on-hand to help you discover the perfect home.

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