Hudson Grandeur
16 guests
8 bedrooms
Cornwall, Orange County
This grand, old home in the Hudson Valley feels like a mix between a beautiful Midwest farmhouse and an English manor. A blue clapboard facade and white bannisters suggest country-chic while the pristine white columns at the entrance add the grandeur.
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.
Hawk & Falcon
10 guests
4 bedrooms
Ulster County, Rochester
Unplug, tune out and drop off the grid for a while. Nestled out of the way in the Rondout Valley in Upstate New York, this secluded barn house and cottage combo is perfect for anyone looking to get away from it all.
Long Point
8 guests
4 bedrooms
Noyack, Southampton
Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.
Explore the 100 most perfect homes in our collection
You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Montauk. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Montauk Home to Rent with a Swimming Pool today, and set up a holiday to remember.
