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.
The Presidential
13 guests
7 bedrooms
Yorkville, Manhattan
Perfect for celebratory occasions, this UES townhouse is a luxury home base for your family reunion, wedding reception, or birthday extravaganza. This home is a certified event space and boasts a personal concierge service plus an impressive list of contacts for all of your hosting necessities.
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.
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 76 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.
