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.
Secret Coves
7 guests
5 bedrooms
Prospect Heights, Brooklyn
Fabulous for family reunions or large group gatherings, this four-story Brooklyn townhouse is a fantastic choice that sleeps up to fifteen guests. Originally built in 1887, many of its original features have been beautifully preserved and you'll be spoiled with choice on where to sleep and socialise - in the chef's kitchen, or the private garden or should you wish to explore, you're moments from the Barclay Centre and the shops and cafes of Prospect Heights.
The Architect's Gallery
10 guests
5 bedrooms
Cairo, New York
This 150-year-old Hudson Valley farmhouse sits on 16 acres of land that includes an apple orchard. It’s an idyllic base for those seeking an escape to the peace of the Catskills – though the town of Windham is just a ten-minute drive.
A Summer's Eve
15 guests
7 bedrooms
Greenburgh, Westchester County
If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.
Explore the 72 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.
