Straight Down the Middle
8 guests
4 bedrooms
Shelter Island Heights, Shelter Island
Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.
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.
Swan's Nest
7 guests
4 bedrooms
Bridgehampton, Southampton
You don't even need to step out of this home to take in the view of Sam’s Creek and Mecox Bay, with the sea stretching out in the distance. At this cottage by the water, built up on stilts, you’ll be able to watch it all from the comfort of home.
Coastal Rhapsody
12 guests
7 bedrooms
Stonington, New London County
If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.
Explore the 112 most perfect homes in our collection
Discover a selection of the best coastal homes in Shelter Island. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book your next getaway today and enjoy a short or extended stay in the best coastal homes in Shelter Island. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
