Why Fall is the Best Season to Rent in the Hamptons

It’s no surprise that summer is what most day-trippers, seabirds and scene-seekers mean when they refer to “Hamptons Season.” Summer in Southampton alone has shown to increase the population by over 80,000. But, if you’ve never experienced fall in the Hamptons, it’s time to add a trip during this shoulder season to your itinerary.   MAXIMUM VALUE. TOTAL BLISS. Let’s start with perhaps the biggest sell: price. “You can rent an oceanfront home in Westhampton for $50,000 in the off-season that would cost $150,000 during the summer months,” says Douglas Elliman agent Lauren Spiegel . You don’t have to rent for the entire month, either. “Usually homeowners tend to stick to a minimum of two weeks when renting, no matter where or when,” advises Spiegel.   PEACEFUL, GORGEOUS ESCAPISM Summer in the Hamptons brings a swelling of sun-filled afternoons and joie de vivre, but it also brings traffic, crowded trains and long waits at your favorite restaurants. After Labor Day, the crowds begin to significantly mellow, yet the weather remains balmy and the oceans are still warm through October.   LOCAL HAUNTS. UNDISCOVERED GEMS. You’ll find no shortage of activities throughout the Hamptons in fall, from pumpkin-picking to wine tours. While at the same time, visiting the Hamptons in the off-season provides an invitation to the less-promoted amenities of the area, including gorgeous hiking trails, stretches of empty shoreline, and offbeat restaurants and dive bars—not to mention, this year, we’re expecting a breathtaking showing of autumn foliage. The only question left is: where to stay?     33 Osborne Lane, East Hampton Village Fringe, New York This newly-renovated six-bedroom, modern barn house rests in the heart of East Hampton. In early October, East Hampton hosts the Hamptons International Film Festival  where you can get a first look at upcoming films and attend conversations between industry personalities, among other events. If you prefer a more private viewing though, plan your own screenings in the state-of-the-art media room. High season: $80,000 Off season: $45,000 Contact agent Tania Deighton for more rental information.     45 Old Depot Road, Quogue North, New York  This four-bedroom, three-bathroom residence is located in Quogue, a historic village in the southern portion of Southampton. In addition to its strong sense of preservation, Quogue is a town for nature-lovers. Spanning 300 acres, the  Quogue Wildlife Refuge offers 7 miles of walking trails that are home to a diverse mix of wildlife including hawks, owls, foxes and a bald eagle. After a day of hiking, return to your temporary homestead at 45 Old Depot Road to make a farm-fresh dinner or warm up in the spacious living room by the fireplace. High season: $30,000 Off season: $6,000 Contact agent  Lauren Spiegel  for rental information.     390 Old Montauk Highway, Montauk, New York Montauk has been affectionately known as the “end of the world” because it is the farthest point east on Long Island’s south shore. From this exquisite five-bedroom, four-bathroom home, you can revel in gorgeous ocean views of Montauk’s coast from nearly every vantage point on the property, or as you stroll along its secluded private beach. Fresh seafood is available in local eateries year round, and even the water sports continue well into fall. With its on-site guesthouse, spa overlooking the Atlantic Ocean, and full-range of impressive amenities (including use of the membership-only famous Montauk Lake Club), you’ll feel worlds away from the hustle and bustle of city life. High season: na Off season: $100,000 Contact agents Susan Ceslow or Jan Nelson  for rental information.     280 Roses Grove Road, Water Nill North, New York Located down a long driveway in Water Mill, this new approximately 8,500-square-foot gambrel-styled home sits tucked away on almost five gorgeous acres, waiting to be discovered by its next visitors. Water Mill is home to the  Parrish Art Museum located in a 14-acre meadow in a Herzog & de Meuron-designed building, and nearby  Hank’s Pumpkintown  has pumpkins of all sizes ready for the picking. Enjoy a day at home, playing tennis, watching films in the movie theater, or relaxing on the large balcony that overlooks Peconic Bay, or return home after a day of sightseeing to breathe in the beautiful surroundings. High season: $100,000 Off season: $50,000 Contact agent  Aaron Curti   for rental information.     40 Dune Road, Bridgehampton South, New York This stunning, Dune Road, modern, bay front home is located south of the highway in Bridgehampton. Fall is a great time to visit Channing Daughters Winery  in Bridgehampton for a wine tasting. While there, you can also appreciate owner and sculptor Walter Channing’s works, which are on display throughout the grounds. Bring home your favorite vintage, and unwind under the stars on the roof-top deck of this approximately 5,100-square-foot, ocean-view home. High season: $400,000 Off season: $250,000 Contact agent Erica Grossman for more rental information.   Want to see more? Browse all our Hamptons rentals here , starting at $4,500.