Villa Menantic
8 guests
4 bedrooms
Shelter Island Heights, Shelter Island
Set across seven private acres on Shelter Island’s Menantic Peninsula, this waterside property epitomises tranquillity. Wake up to views on one of the home's two private balconies, before whipping up breakfast in the state-of-the-art kitchen and sipping your morning coffee as you paddle in the sea.
Whale Watching
8 guests
4 bedrooms
Sag Harbor, Southampton
Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.
Seascape
8 guests
5 bedrooms
Noyack, Southampton
A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.
Art & Nature
6 guests
4 bedrooms
Cragsmoor, Wawarsing
This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike.
Explore the 566 most perfect homes in our collection
Spacious 2 bedroom homes in Shelter Island. 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 bedroom homes that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
