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.
The Old Life-Saving Station
13 guests
6 bedrooms
East Marion, Southold
Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman.
Sea Urchin Escape
6 guests
3 bedrooms
Provincetown, Barnstable County
On the very tip of Cape Cod's curved finger, Provincetown is an East Coast beach destination like no other. Not overly developed, it's managed to retain its small-town vibe and reputation as a haven for artists and writers.
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 116 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.
