The Pond House
5 guests
3 bedrooms
Woodstock, New York
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.
Shelter Island Homes for a Hiking Trip
We selected the 132 homes worth renting in this location
Home spotlights in Shelter Island
A Timeless Tale
6 guests
3 bedrooms
Greenwood Lake, Warwick
Although a modern build, this home was designed with the craftsman style in mind. It has a twenty-first century edge that gives it just enough luxury to make it both homely and wonderfully opulent for that perfect vacation.
Soul Of The Willow
6 guests
3 bedrooms
Ulster County, Woodstock
What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock.
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.
We selected the top 3% holiday homes in Shelter Island Homes for a Hiking Trip
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Explore our collection of homes for a hiking trip in Shelter Island. They are perfect to relax in after a day of exploring the outdoors. They 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 most beautiful homes for a hiking trip in Shelter Island. Our team of Plum Experts are on-hand 24/7 should you need anything.
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