Tudoresque
10 guests
5 bedrooms
Ossining, Westchester County
In the town of Ossining on the banks of the Hudson River, this home is reminiscent of an English Tudor mansion on the outside. Inside, there’s plenty of social space for the group to spread out – playing a game of pool in the main living room, settling in to watch Netflix by the fire, in the dedicated media room upstairs or perhaps sipping an old fashioned at the wet bar in the “sky lounge” at the top of the house.
Brooklyn Muse
10 guests
5 bedrooms
Bedford-Stuyvesant, Brooklyn
Step inside this home and you'll be welcomed by the owner’s creative spirit. From the original artworks, handcrafted elements and stylish furniture, every detail has been considered to provide the ultimate city sanctuary.
Creek Farm
10 guests
5 bedrooms
East Quogue, Southampton
Grab the whole family for a most delightful trip to the Hamptons when you stay at Creek Farm. This family-friendly home was built in the 1860s and while it has been updated since then, it is still very much an old home with all the joys that come with it.
Explore the 78 most perfect homes in our collection
Spacious 5 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 5 bedroom homes that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.
