142 Middle Line Highway, North Sea
Memorial Day to Labor Day: $450,000Coming with many different solo month rate options, ranging from $75,000 for June to $200,000 for August, this North Sea mansion seems destined for sharing. With a main house and guest house, it boasts 8,457 square feet and seven bedrooms as well as amenities like a huge recreation room, wet bar, and outdoor shower.Christopher J. Burnside and Aubri Peele of Brown Harris Stevens have the 2.8-acre listing.
15 Dune Road, Bridgehampton
August through Labor Day: $975,000Designed by Mark C. Matthews Architecture in collaboration with Francis D’Haene of D’Apostrophe Design Inc., a waterfront modern on Dune Road is the most expensive to rent of this bunch. Enjoy 360-degree water views through wrapping walls of glass while relaxing inside or walk the home’s private path to the beach for fun in the sun. At such a high price point, the lucky renter will likely want to use every inch of the property every minute they have it.Catherine Juracich, Thomas Ventura, and Alexis Godley of Douglas Elliman have the lavish listing.
9 Gull Rock Road, Sag Harbor
June: $45,000 | July: $90,000 | Memorial Day to July 31: $135,000Newly constructed in 2021, you can be part of one of this Sag Harbor property’s very first summers. Christening the modern, shingle-style beauty can include lounging by the pool, walking to the nearby private beach, or riding the two vintage Gary bikes that come with the rentral.Barbara Lobosco of Douglas Elliman has the listing.
27 Ezekills Holw, North Haven Village
July/August through Labor Day: $350,000There’s nothing like looking out at the water while swimming in the pool or chatting by the fireplace, and a home in North Haven offers exactly that. Multiple areas for entertaining outside and warm yet bright interiors— defined by wood-beamed ceilings, clean lines, and a soft palette—make it a stunning summer backdrop.The Atlantic Team at Douglas Elliman has the listing.
Hampton Road, Village of Southampton
June Rental: $25,000 | July Rental: $35,000 | August Rental: $45,000This Southampton Village home is perfect for the avid shopper or foodie who loves to walk to town and doesn’t mind sacrificing a pool. Built in 1915, the quaint 1,918-square-foot home has three bedrooms so visitors can come stay, too.With the beach just moments away, this rental represented by Cristina Matos and Gertrud Hoertnagl-Pereira of Brown Harris Stevens could be just the right fit for you and family or friends.
216 Sagaponack Road, Bridgehampton
August through Labor Day: $200,000For elevated, countryside living, a Bridgehampton estate offered for rent for the first time ever is a beautiful contender. The 4,000-square-foot home, set on over five acres, is stylishly furnished throughout with unique artwork to take in as well. Gardens perfect for Fourth of July picnicking and a long pool set a classic Hamptons scene.Catherine Juracich and Thomas Ventura of Douglas Elliman hold the listing.
39 Roxbury Lane, Wainscott
Memorial Day to Labor Day: $100,000Privacy and ease are a given at this rental in Wainscott adorned with hyrangeas and surrounded by thick trees. Spread across just one level, you’ll find three bedrooms, generous living spaces, a top-grade kitchen, and more inside. Just beyond the glass doors, a heated pool awaits.Katherine Casey and Miles Bouckoms of Douglas Elliman hold the rental listing.
