Wainscott Woods Retreat Homes for Two People

We selected the 700 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

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Home spotlights in Wainscott Woods Retreat

Woodland Hymnal

Woodland Hymnal

  • 4 guests

  • 2 bedrooms

Woodstock, Ulster County

This beautiful old clapboard church has been turned into a woodland retreat like no other, where deer regularly stroll among the trees. Just outside Woodstock, there are craft beer breweries, farm shops and mom and pop coffee shops a short drive away, and trails into the Catskills are all around.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

This characterful beach house is located in a quiet neighbourhood of Centerport, perfectly placed for you to explore Long Island. Perched on the headland, it boasts spectacular bay views.

We selected the top 3% holiday homes in Wainscott Woods Retreat Homes for Two People

Explore the 700 most perfect homes in our collection

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Most popular homes in Wainscott Woods Retreat

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Woodpecker's Stop

Woodpecker's Stop

  • 2 guests

  • 1 bedrooms

Ulster County, Woodstock

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

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Frequently asked questions

Explore our collection of homes for 2 people in Wainscott Woods Retreat. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 2 person homes that Wainscott Woods Retreat has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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