Wainscott Woods Retreat Unique Homes

We selected the 914 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Wainscott Woods Retreat

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

This Hamptons home does island life the modern way. In the mornings, hit up the local farmers’ markets and seafood shops.

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

Sitting alongside an enchanting creek, this cabin is a tranquil haven with a lot to offer. From the hot tub and wood fired sauna to the beautiful views, this is the perfect setting for a refreshing and romantic retreat.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.


We selected the top 3% holiday homes in Wainscott Woods Retreat Unique Homes

Explore the 914 most perfect homes in our collection

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Most popular homes in Wainscott Woods Retreat

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

A Faithful Friend

A Faithful Friend

  • 10 guests

  • 6 bedrooms

Water Mill, Southampton

Zephyr Residence

Zephyr Residence

  • 10 guests

  • 5 bedrooms

Water Mill, Southampton

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Kennedies

Kennedies

  • 9 guests

  • 4 bedrooms

North Sea, Southampton

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Frequently asked questions

Plum guide offers a handpicked selection of the most unique homes in Wainscott Woods Retreat. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and secure the most unique home in Wainscott Woods Retreat for your next getaway. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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